Pharmaceutical Review

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Pharmaceutical
Kremers
Edward
Hoffmann,
Frederick
>
/
I
Pharmaceutical Review.
Founded in 1882 nv
DR. FREDERICK HOFFMANN.
Edited by
DR. EDWARD KREMERS.
WITH THE CO-OPERATION OF
Dr. Dasiel Base, Professor oJ Chemistry, Prof. J. U. LlOYD, Professor of Chem
University of Maryland. Department istry, Cincinnati Eclectic Medical In
of Pharmacy, Baltimore. stitute, and Pharmaceutical Manu
Prof. J. H. Beai., Professor of Applied facturer.
Pharmacy, PittflburgCollege of Phar Dr. A. B. Lyoss, Pharmaceutical Chemist,
macy. Detroit, Mich.
Dr. I. W. Brasdel, Assistant Professor Mr. Harry B. MaBos, Editor Bulletin of
of Organic Chemistry, University of Pharmacy, Detroit, Mich.
Washington.
Dr. Cbabi.es E. CaBpabi, Professor of Dr. F. B. Power, Director of the Well
Chemistry and Physics, St. Louis come Research Laboratories, London,
College of Pharmacy. England.
Dr. Viroil Coih.estz, Professor of Chem Prof. W. A. Puckser, Professor of Chem
istry and Physics, New .York College istry, University of Illinois School of
of Pharmacy. Pharmacy.
Dr. R. Fiscrer, Assistant Professor of Dr. J. 0. SrHi.oTTEbHEcK, Professor of
Practical Pharmacy, University of Pharmacognosy, University of Michi
Wisconsin. gan.
Dr. H. M. GobDtN, Professor of Organic Dr. A. B. Stevess, Professor of Phar
Chemistry and Drug Assaying, North macy, University of Michigan.
western University School of Phar Dr. R. H. True, Physiologist in charge
macy. of Drugs and Medicmal Plants,
Dr. H. Kraemeu. Professor of Botany Bureau of Plant Industry, Depart
and Pharmacognosy, Philadelphia ment of Agriculture, Washington,
College of Pharmacy. D. C.
VOL. XXYI.
MILWAUKEE,
Pharmaceutical Review Publishing Co.
1 80S.
TABLE OF CONTENTS.
Editorial. . Page
An object lesson in the enforcement of pure drug legislation 225
Association of state and national food and drug departments 257
American Pharmaceutical Association 289
Contributions.
German pharmaceutical institutes. By Edward Kroners 1
Progress in alkaloidal chemistry during the year 1906. By H. M.
Gordin 9, 33, 70, 107
Historical fragments.
14. Pharmaceutical notes from Nuttall's Journal of Travels in
Arkansas Territory. By Edward Kremen 19
Assay of fluidextract of belladonna leaves. By A. B. Lyons '22
Plant pigments. By /. W. Brandel. 44, 65, 119, 141, 185, 215, 279
Percolation. By /. W. Brandel and Edward Kremers 51, 74, 208
The volatile oils, 1901— 03. My /. IF. Brandel 56, 88, 246, 271, 371
Hematoxylin as an indicator in the titration of phosphoric acid. By
A. B. Lyons 97
The isoterpeues of Flawitzky. By Edward Kremers 102
Some chemical remarks on the citro compounds of iron. By ./. E.
Gerock 129
Citro-compounds of iron. By A. B. Stevens 131
The estimation of hydrastine. By W. A. Puckner 132
The cultivation of hydrastis. By John Uri Lloyd 138
Phytochemistry in America.
1. Helen Cecilia DeSilver Abbott. By Nellie Wakenmn 151
2. Henry Trimble. By Nellie Wakeman 3118
The apothecary — a literary study. By Edward Kremers.
2. Du Mein Jena 153
3. Kussmaul, Jugenderinnerungen eiues alten Arztes 252
Beschreibung aller Staude auf Erden 342, 358
Table for preparation of alcoholic menstrua. By A. B. Lyons 161
Phytochemistry and hay fever. By F. Rochussen 170
PhytochemicBl notes. From the laboratory of Edward Kremers.
68. California eucalyptus oils 177
69. Quantitative determination of oxidase in the leaves of
Monarda fistulosa. By Nellie Wakeman 314
Some genera1 observations on the United States Pharmacopoeia. By
Benj. L. Murray 193
Literature on medicinal plants and drug plant culture. By Albert
Schneider 201, 236
Page
Deficient drugs and galenicals.
1. The deterioration of spirits of nitrons ether. By Richard
Fischer 227
Notes, mainly bibliographical, on two American plants. Sleepy grass and
Creosote bush. By Albert C. Crawford 230
Coniferous oils of the Northwest. By I. W. Braadel.
1. Oil from tie leaves of Red Cedar. By A. H. Vewey 248
2. Needle oil from Douglas Spruce. By Maude Sweet 326
Deterioration of some standard pharmaceuticals. By A. E. Barnard., 308, 321
Thymoquiuone and bydrothymoqninone. By N. Wakemao and
' E. Kremers 329, 364
Precipitated sulphur. By S. M. Sorley 353
Books reviewed.
American Pharmaceutical Association — Proceedings 128
Bartley, E. H. — Manual of physiological and clinical chemistry 30
Baumert, G. — Lehrbuch der gerichtlichen Chemie 158
Ileckarts, H. — Jahresbericht der Pharmazie 127
Jahresbericht der Pharmazie 384
Cohlentz, V. — The newer remedies 223
Crawford, A. C. — The supposed relationship of white snakeroot to
milk sickness 126
The use of suprarenal glands in the physiological testing of drug
plant* 427
(See Marsh, C. D.)
Dawbarn, K. H. M. — An aid to materia medica 283
Dorveaux, P. — Les pots de pharmaeie 286 ,
Ebert, A. E.~ (See Hiss.)
Enter, II. von. - Grundlagen und Ergebnisse der Pflanzenchemie 319
Gerard, E. — Traitd pratique d'analyse des deurees alimentaires 381
Gily, E. (See Koch, L.)
Green, J. K. — An introduction to vegetable physiology 31
Hinkle, A. — American root, drugs 126
Cultivation and handling of golden seal 283
Hiss, A. E. — New Standard Formulary 333
Holmes, E. M. — Museum report 26
Klugh, G. — (See Henkle, A.)
Koch, L. — Pharmakuostisches Praktikum 28
Kraemer, H. — A textbook of botany and pharmacognosy 377
Lenz, W. — Medizinische Untersuchungen fur Apotheker 30
Lloyd, ■/. U. if C. G. — Hydrastis canadensis 379
MaeEwan, /'. — The art of dispensing 316
Maiden, .1. H. — A critical revision of t he genus eucalyptus 126
Mahnejac, F. — Comment {purer son eau 221
Marsh, C. D. — Results of loco- weed investigations in the field, and
laboratory work on loco-weed investigations 160
Mason, H.' IS. — Window displays for druggists 150
195350
PaIse
Merck, E. — Annual report 192
Meyer, H. — Determination of radicles in carbon compounds 286
Natl. Syl. Com. — Report of progress 351
Noyes, W. A. — Kurzes Lehrbnch der Chemie 180
Puckner, W. A. — A laboratory outline of quantitative analysis 351
Rambnud, P. — La pharmacie en Poitou 25
Robin, A. — Les ferments mdtalliques 280
Ruddimann, E. A. — Manual of materia medica 27
Incompatibilities in prescriptions 349
Sacken, L. — Die chemisette AfHnitat and ihre Messuug 281
Schimmel & Co. — Works, Miltitz near Leipzig 352
Schmidt, J. — Synthetisch-organische Chemie der Neuzeit 28.1
Senfeldder, L. — Dispensatorium pro pharmacopoeis Viennensibus in
Austria 254
Squibb, E. ft — Materia medica ■. 222
Stewart, F. E. — A compend of pharmacy 381
Thoms, H. — Arbeiten aus dem pharmazeatischen Institut der Univer-
sittit Berlin 222
Thorp, V. H. — Outlines of industrial chemistry 187
Tingle, J. B. — (See Meyer, P)
Tschirch, A. — Die Chemie und Diologie der pflanzlichen Sekret<> 316
Haudbuch der Pharmakognosie 317, 349
INDEX OF AUTHORS.
Allen, C. E. 32
Barnard, H. E. 308, 321
Bradley, H. C. 30, 31
Brandel, I. W., 44, 51, 56, 65
74, 88, 119, 141, 185, 215, 246, 248, 263, 271, 279, 281. 326, 371
Crawford, A. C 230
Denniston, ft. H., 126, 282
Dewev, A. H, 248
Erlanger, J., 126, 127
Fischer, ft 227, 381
Gerock, J. E. 129
Qordin, H. M. ; 9, 33, 70. 107
Kahlenberg. L., 281
Kremers, E. 1, 19, 20, 27, 51, 74, 102, 128, 153, 157, 159, 100, 177
187, 188, 192, 221, 222, 223, 225, 252, 254, 257, 263, 283, 284
286, 289, 316, 319. 329, 342, 351, 352, 358, 364, 379, 383, 384
Llovd, ./. U., 138
Lyons, A. B 22, 97, 161
Murray, Benj. L. 193
Puckner, W. A 132
Rochussen, F., 167
Schtotterbeck, J. O., 29, 317, 349
Schneider, A 201, 236
Sorley, S. M. 353
Stcvens, A. B., 131, 316, 349
Sweet, M., 326
True, ft. H. : 377
Wakeman, N. A 151, 314, 331, 338, 364, 381
SUBJECT INDEX.
Page Page
Abbott, Helen Cecelia <te Sllver 151 Bellis perennls 72
Abrus precatorlus 188 Benzoin odorlferum 207
Acaccla gregli ■ ■ • ■ 235 Berberis auulfolium 203
Acer. pseudo-platanus 142, ilo Blxa orellana 207
Achillea millefolium 71 Blumea balsamlfera 208
Aconltum napellus 125 Borago officinalis 69
vulgare 12© Bourbon rose. 'Hermosa' 141
Aesculus hippocaslanum 45 Budlera globoaa 123
pavla • • 142
Agave Americana 209, 213 Cactus flagelllformls 70
Ajuga reptans 1*0 grandlflorus 237
Alcoholic Menstrua, tables for..... 161 phyllanthus 70
Algarobla glandulosa 205 speclosus 70
Alkaloids (See Gordln). Caffeine 76
Allium nigrum 123 Chrysanthemum blcolor 7Z
schoenopros 123 Calceolaria rugos 143
Alopecuras genleulatus 230 Calendula offlcinalls 72
Alplnla offlclnarum 203 Calllopsls blcolor 72
Alstonla constrlcta 212 Calllstephus chinensls 72
Althaea rosea 123 Calycanthus florldus 70
Ambrosia artemlslafolla 171 Camella Iaponica 144
Amer. Pharm. Assn 289 species 144
Ammonia water, deterioration of.. 321 Campanula glomerata 70
Amonum angustlfolium 90 grandlflora 70
Amygdalus communis 213 perslcifolla 70
Anchusa offlcinalls 69 pyramydalis 70
Andropogon citratus SO ranunculoldes 70
nardus 60, 02 Camphorasma monspellca 95
schoenanthus 60 Camphor spirits 112
Anemone hortensls 141 Canna indlca 143
pavonlna 1*1 ■ llmbata 143
Anemopsls Callfornlca 211 Caparls splnosa 70
Anoda hastata 124 Carduls species 72
Anthemls tlnctorla 71 Carlca papaya 210
Anthoxanthum odoratum 230 Carterla larreae 234
Antirrhinum majus 143 Cascara sagrada 214
Aplum graveolens 203 Cassia llgnla j7S
Apothecary in literature Ilgustrina 1*£
135, 252, 342, 358 Castanea punula 210
Aquilegla speclosa 141 Cedronella cana 120
vulgare 125, 141 Cedrus atlantlca 58
Arctolls grandlflora 71 libanl ■ • 58
Areca catechu 209 Celosla crlstata 66, 09
Arlstolochia glauca 64 plumosa • • 69
Artriplex hortensls 71 Centaurea cyanus 68, 72, 216
Arundo phragmltes 230 gymnocarpa 72
dracunculuB 69
Arundo phragnutes 230 scablosa '«
Asarlum arlfollum 94 Cephalanthus occldentalls 208
Ascleplas currasavlca 69 Ceratostigma plumhageoldes 125
tuberosa 69 Cherlanthus chelri 45
Asplenlum Fellx foemina 204 scoparius k , 45
Assay of fluid extracts , 22 (Levkoy) 45
Aster 71 Chenopodlum Californicum 43
chinensls 71 Cichorlum cruenta 72
movaeangelae 71 lntybus 72
tenella 71 Clnnamonum Ceylanlcum ;iTd
wild 71 pedatlnerlvum • • 275
Atlanthus glandulosa 211 Cltro compounds of iron 129. 131
Avena sativa 230 Citrus decuvnara 142
Azalea pontlca 119 Clematis integrlfolla 141
Clitorla ternatea J"
Belladonna, assay of 22 Cochiearla officinalis 277
Page Page
Coniferous oils of N. W 248 Geranium 119
Convallarla majalls 88, 208 ■ robertinnum 120
Convolvulus arveusis 73 sangulneum 120
tricolor 73 Gilgiu aggregata 125
mauritlanus 73 Glauclum llavlum 207
tricolor 73 Glycerla aquatlca 230
Coriandrium sativum 144 Gossyplum berbaceum 47, 124
Cornus mascula 119, 216 Grlndella robusla 237
Coronilla varia 122
Cosmos 72 Haematoxylum campecheanum 48
Covlllea tridentata 232 llagenla abysslnica 207
Crataegus oxycantha 45, 141 Hay fever and phytochemistry 167
Crauca papaya 214 Hedera helix 208
Creosote bush 233 lledysarnm carouarlum 122
Crocus maeslacus 120 Hellanthus annus 73
salivus 120 tuberosus « 239
Croton procumbeus 205 llelichrvsum arenarlum 73, 218
Cryptomeria japoulca 59 bracteatum 73, 218
Cuphea mlnlata 72 monstrosum 73
vlnosa 72 Hellotropus peruvlanum 70
Cynoglossum officinalis 69 Hematoxylin, as an indicator 97
Cvpripedlum pubescens 212 Hemerocallls fulva 123
spectabile 42, 203 Hesperis malronalls 119
Iloteromelas arbutifolla 211
Dahiia variabilis 08, 72 Hibiscus rosa sinensis 124
Dairy and Food Dep'ts 257 — syrlacus 124
Dammarla australis 42 Hortensta speciosa 142
orientalls 59 Humulus lupulus 207
Daphne mezerum 144 Hyaciuthe 123
Delphinium consollda 40, 141 Hyaclnthus botryoides 123
discolor I'll Hybrid tea rose 141
formosum 141 Hydrangea quercifolla 142
hybridum 141 Hvdrastlne, assay of 97
— Zalil 45, 141 Hydrastis, cultivation of 138
Deterioration of ammonia water... 321 Hydrothymoqulnone 329
of lime water 323 Hyoscyamus, assay of 24
of spirits of camphor 312
of tincture of iodine 308 Iberis umbellala 119
Dianthus cartham 71 vlolacea 119
carlhuseanorum ^1 Dllcium rellglosum 96
caryophyllus 71 Impatlens balsamlna 120
chalcedonla 71 Indlgofera tinctorla 47
species 71 Iodine, tincture of 319
Digitalis purpurea 143 Ipomoea mutabllls 73
Drug plant culture 201 purpurea 73
Drugs and galenicals, deficient. (See Iris croacata 120
Contributions.) florentina 61
■ hispanlca 120
Echinacea angustlfolla 211 hortensls 120
Evhium pyrenalcum 69 pumila 120
vulgare Iron, citro compounds of 129, 131
Elettarla cardamonum 90 Irntls tlnctora 47
F.rysinum officinalis 119 lsoterpenes of Flawitzky 102
perofsk 119 Ixla crocata 120
Ervnginm aquatlcum 20
Eschscholtzla Callfornlca 206 Jena, du mein '53
Eucalyptus globulus 177
Fupatorlum ageratoides 126 Knempferla galanga 89
Euphorbia eremocarpus 241 Kalmla latlfolla 210
ocellata 211 Kussmaul —>-
Fablana indlca 143 Dac sulphurls 353
Flawltzkv. lsoterpenes of 102 I.agerstroemla indlca 67, 123
Food and Dairy Dep'ts 257 I.amium maculalum 1-1
Fouqulera splendens 152 — purpureum 121
Krltlllarla imper 123 I.antana camara 14*
Fuchsia procumbens . , 124 delicatisslmum 144
Fumarla officinalis 119 I.arrea mexlcana j33
I.athyrus latlfollns 122
Gallinum mollugo 142 - odoratus 12-
vernum 142 tlngltanus 122
Gurrya fremontli 214 l.aurus benzoin -1
Caultheria procumbens 188 Davateria trlmestris 124
Cuura biennis 124 Leucojum vernum 09, -10
Gazarrla rlngens 73 I.iastrls odorntissima -'12
Gelsemlnm sempervlrena -06 I.IIinm candidnm 123
Genista tinctorla 12<- tlgninnm splendens 12J
Gentlana aculis 119 I.lme water, deterioration of 323
Page Tage
Llnarla cymbalarla 143 — — Cltronella 62
vulgaris 143 — — Convallaria majalls 88
i. muai pyrenne 1-3 Cryptomeria japonlca 59
syriacum 123 Damuier orlentalis 59
Liquid amber styraeltlua 21 Douglas spruce 32(1
Lobelia cardlnalla 07, 70 Eucalyptus, California 177
erlnus 70 —■ —• Ualangal 89
■ syphilitica 70
Lophauthes anlsatus 121 —• — Geranium,
Ginger East Indian 59
89
Lotus cornlculatus 122 Hops 92
Luplnua crulckshankll 122 —■ — Kaempferla galanga 89
mutabilis 122 Laurel leaves 276
Lychnis chalcedonla 71 — - — Lemon grass 66
Lyclum barbarum 143 Mace 240
l.ycopodlum clavatum 212 — — Matlco 91
Lysomacbla numularia 120 Musiard 277
Nlgella 95
Maha parrgirl 62 Nutmeg 246
Ma I v:i rosea 124 — — Onion 88
rotundlfolln
• sylvestrls 124
124 Orris 88
— — Pulmarosa 1.. 59
Marah murlcatus 210 — — Pepper, black 91
Marrublum vulgare 214 Plper famechoni 91
Medleago sativa 122 — — Polygonlum perslcarla 94
Medicinal plants, literature on. 201, 236 — — Rose 371
Megarrhiza Caltfornlca 208, 241 — — Sandalwood 92
Metanicotlne 9 Sasafras 276
Metrosideros lanceolata 124 Savin 56
semperflorens 124 Spoonwort 277
Mieromerln douglasll 207 Star anise 95
Milk of sulphur 353 — Japanese 95
Mimulus glutinosis 238 — — Tul>erose 64
MlraMUs jalapa 124 1'ganda aloe 64
Monardas 329, 364 Vetlver 61
Monarda coccinea 121 Ylangylang 90
■ didyma 07, 121 Olea Europa 237
■ ecarlate
flstulosa 121
121, 314 Onanthrlx decumbens
Orchis coriophora
211
124
Morpnenol 12 —■ — vernus 124
Morphine 1- Oreodaphne Californlca 208
Murraya exotica 142 Oxalls tetraphylla 125
Mydriatic alkaloid 18 Oxidase, determination of 314
Myristica fragrans 246 Oxycodelne 33
Mysotls palustrls 70
versicolor 70 Panlcularia aquatica 230
Papaver bracteatum 125
Nepeta catarica 121 burzerli 125
Nlgella damascena 95, 141 nudlcaule 125
Nlcotiann virglnlana 143 pvrenaicum 125
Nonea rosea 70 rhoeas 125, 220
NuttaU's journal of travels 19 Paspalum scroficulatum 230
Pelargouium inquinans 120
Oenothera 124 peltatum . . 120
■ aculis 124 — — species 120
grandlfiora 124 zonale 120
speclosa 124 Pentslemon rtlffusum 143
Oil of Aloe Uganda
.—■ — Alpinia maiactensis 64
89 Percolation (See Contributions).
Petunia hvbrida . . ■. 143
Apopin 276 Pharmaceutical Institutes, Berlin.. 1
—.
—— —■ Asarum arlfolium
Atlas cedar 94
58 Pharmaceuticals, deterioration of.. 308
Pharmacopoeia. V. S 193
Beech seedlings 91 Phaseolus multiflorus 122
• Black pepper 91 Philadelphia caronaria 142
Boldo leaves 246 Phosphoric acid, titration of 97
Calamus 63 Phragmltes vulgaris 230
Cameroon cardamon 90 Photochemistry and Hay fever.... 167
— — Camphor 247 Photochemistry in America (See
— —. Canada Camphorosma
snake.root
Monspellaceae 9495 Contributions).
Phvralis alkekenkl 144
— — Cananga 90 Pigments, plant (See Brandel).
Cardamon. Ceylon 90 Pigmentation, plant, theories of. . . 145
Cassia 274 Piper famechoni 91
Cedar, atlas 58 Pipeiidene 87
— red 248 Pisum sativlum 122
— — Ceylon cardamon 90 Podalyrla anstralls 122
■ cinnamon 273 Polemonlum coeral. grandfl 120
—■ — Cinnamon. Ceylon 273 Polyanthus tuberosa 64
leaves 274 Polycala amara 125
— pedollnervlum 275 vulgare lz«
Page Page
Polygonium perslcarla 94 ulmaria 142
tlnctora i 47 Spirits of camphor 312
Potentilla formosa 141 Spirit of nitrous ether 227
— — reptans 141 Stlpa caplllata 232
Power, V. P., opposite page 193 hystriclna 233
Primula verls 12o inebrians 232
Pulmonarla angustlfolla 70 leptortachya 233
officinalis 7O neeseana 232
Panics granatum 204 parvlflora 232
Purine — — prlnglll 233
Pyrethrum clnerarlaefollum 212 siberica 232
vaseyl 232
Quinine 7O virldula 232, 233
— robusta 232
Khamnus Californiea 204, 207i Sulphur, precipitated 353
frangula 215 Symphytum officinalis 73
purslilana 207
Rhododendron arboreum 119 Tanacetum vulgar? 73
— — occldentalls 238 Thalleroquln 84
Rhus cotlnus 186 Thi.a viriilis 211
Rlclnus communis 109 Thebaine 86
Roblnla hispldla 122 Theobromine Ill
pseudacacia 45, 122 Thuya glgantea 248
Rosa alba 373 menzlesil 248
—— centifolla 142, 3< 3 pllcata 248
—. — «lnnnamonea 142 Thymoquinone 329, 364
damascena 373 Thymoqulnhydrone 330
galllca 142 Thvmus serphylllum 121
odorata 141 Tincture of iodine 309
Rose, hybrid tea 141 Tobacco alkaloids Ill
Rumez hymenocepalus 218 Trlfollum agreatls 122
Ruta graveolens 216 — pratense 122
Trimble, Henry 838
Sabai serrulata 214, 237 Tiompneolum majus 120
Salvia alttssima 121 Tropeines 117
— — azurea 121 Tulfpa ovulus soles 123
■ cocclnea
neoiorosa 121
121 U. S. P., some general observations 193
nobllis 121 Veratrum nigrum 123
— — officinalis 121 Verbascum nigrum 143
palustris 121 thapsus 143
Pitcheri
■ pratensls 121
121 Verbena hybrlda 144
. officinalis 144
serphyllum 121 (red) 144
— — sylvestris 121 tenera maonetta 144
Sambueiis nigra 70 Verontea agrestls 143
Saponarla officinalis 71 • chamaldrys 143
Saraca lndlca 151 spicata 143
Sassafras officinalis 214 triphyllos 143
Schinus molle 211 Viburuum opulus 7O
Scllla amoena 123 Vlcea faha 122
campanulata 123 Vlgna sonensls 23,1
slblrlca 123 Vlnea minor 69
Scutellaria 47 Viola cornuta 144
Serratula species 73 maxima 144
Sllene armerla 71 tricolor 144, 210
Sleepy grass 230 Viola (Violets) 144
Solanlnl 80 Volatile oils. (See Brandel.)
Solanum dulcamara 144
sodomalum 81 Xylopia ethiopica 96
Sophora Iaponlca 122, 216
Sparteine 81 Yerba santa 241
Spartlum scoparlum 122 Yucca angustlfolla 1»2
Spathyema foetlda 279
Spirea fillpendula 142 Zinnia elegans 73
opullfolla 1*2 Zygadenus fremontll *<»
VOLUMK 2<i. JANUARY, 1908. Number 1 .
German Pharmaceutical Institutes.
I. Pharmaceutical Institutes of the University of Berlin.

Pharmaceutical science as well as pharmaceutical education in
Germany has received a new impetus with the establishment of two
new university institutes, viz. at Berlin and Strassburg. More(>j?er,
the prospects for a third seem favorable. That the establishment of
Laboratory for Qualitative Analysis.

This cut gives a good Idea of the general arrangement of the general laboratories.
these institutes should be contemporaneous with the advanced

requirements made in the education of the German pharmacist makes
them appear as an outward expression of a general forward move
ment on the part of German pharmacy. This is gratifying indeed,
(1)
2 PHARMACEUTICAL REVIEW.
for the tendency toward commercialization has made itself felt in

Germany as well as e. g. in England and the United States, though
outwardly it did not become so apparent. German pharmacists are,
therefore, to be congratulated that while they have not tried to
check wholesome commercial development, they have stemmed the
tide of commercialization of their venerable calling by the creation
of new scientific and educationul organs. That they have succeeded
in reasonable measure is shown on the one hand in the healthy
growth of the German Pharmaceutical Society, a creditable counter
part to the German Chemical Society; on the other hand in the
Factory.
Extraction apparatus and evaporating pan to the right. Still with vacuum pump,
centrifuge and shaking apparatus to the left.
response on the part of the government to the continued demands

for adequate homes for pharmaceutical students at German uni
versities.
If it seems strange to pharmacists on this side of the ocean, that
Fliickiger should have died without witnessing the erection of a
pharmaceutical institute at the University of Strassburg, where he
was active so many years, whereas so many other branches of
learning were provided not only with adequate but elegant homes;
PHARMA CEUTICAL REVIEW. 3
how much more surprising is it to contemplate the fact that the

university at the Prussian and Imperial Capital has been without a
pharmaceutical institute throughout the nineteenth century. The
first Chemical Institute built by Hofmann was not only supplemented
by a second institute, but has recently been replaced by a new
structure. But during these decades of intense chemical activity,
the pharmacy student was merely tolerated and when in 1895 the
Prussian government finally took a new start, the pharmacy student
had to go begging for a place in which he could work.
This indifference, not to say hostility on the part of the University
as well as the government seems all the more inexplicable when one
Poppy Garden.
The Pharmaceutical Institute (rear view) stands on a corner of the new Botanical
Garden. Aside from the medicinal plants exhibited in the Garden,
a plot of Itround has been set aside for the cultivation
of plants for phytochemlcal research.
recalls the fact that the first professor of chemistry, M. H. Klaproth,

at the University of Berlin was a pharmacist and that later phar
macists played no small role in the developement of chemistry at
the Prussian capital. One need only recall the names of Hermbstadt
and Heinrich Rose. And yet to him who is at all familiar with the
position which pharmacy has occupied among the professions, who
. knows how pharmacy has been treated with possihly few exceptions
at all our larger institutions of learning, to him the history of
pharmaceutical 'education at Berlin reads like an old story. The

same struggles, the same indifference and even animosity, both
within and without. However, the saddest aspect of it all is this>
that the pharmacists themselves have not demanded, in clear 'add
unmistakable terms, that representation for their ancient', and
honorable calling at the highest institutions of learning which it
deserved.
To relate, even in general outline, the developement of pharma
ceutical education at Berlin before the dedication of the Pharma
ceutical Institute at Dahlem, 'ds not necessary int.this brief sketch.
Those who are interested in pharmaceutical education will await
with interest the complete historical account which we may expect
from the present Director in 1910, at which time the University
expects to celebrate its first centenary. Our present object is not
to look backward, but to acquire an insight into what the new
Cellar.
1—10. Gen ral storage rooms etc. 20. Coal cellar.
11. Koom lor ga* meters. 21—24. Stairways.
12—14. Pipes tor beating etc. 25. Ether storage,
in. Steam radiators. 26. Acid storage,
lfi. Ventilator and air filter. 27. Ventilator for the large lecture
17. Accumulators. room.
18. Engine room and bench for 28. Steam radiators.
engineer. 29. Air filter.
19. Boiler room.
Institute has already done in the few years of its existence, making
this the criterion for what we may expect in the future.
Neither is it the intention of the writer to give a detailed account
of the building or of its equipment. A description of the building
has already been supplied by Dr. G. Fendler* and a detailed
description of the equipment may be expected from the Director
himself within a few years.
While the words spoken by A. W. v. Hofmann at the unveiling
of the Wohler statue at Gottingen in 1890, viz. "Es kommt nicht
• Apotheker Zeltung, 1908.
FH A KMA CE VTICA /" REVIEW. 5
auf den Kiifig an, die F rage list, ob der Vogfll, der drinnen sitzt,
singen kann," is as true today;as it was in the early days of labor
atory instruction ; yet it is undoubtedly equally true that Hofmann
himself could not have accomplished what he did without his
Chemical Institute which was regarded as magnificent in its day.
The floor plans of the Dahlem Institute which are herewith
reproduced, also the few views of the interior, will give a better idea
than could be conveyed by words of the scope of the work whicl^ is
contemplated and carried out.
In order better to appreciate the facilties for instruction it is
necessary to know the number of students who have taken part in
the laboratory instruction. Thus e. g. 101 students participated
during the winter semester 1902—03, and 118 during the summer
Basement
80. Vacuum distillation. hi Refrigerator,
81 —3<>.Toilets and laboratories. h Cabinet 'tor apparatus
37. Koom for heating sealed tubes. k) Centrifuge, shaking appara
38. Electro-chemistry. tus, vacuum pump.
31i.Elementary analysis. 1) Still,
40—45? Corridors and stairways. m) Table,
46. Main entrance. n)
47. Vestibule. 52. Engine room.
4S. Entrance to the wing. 53. Wjish room.
49. Entrance to the large lecture 54. otHce of superintendent of build
room. ing.
50. Laboratory for preparations. 55. Elevator.
51. Factory, 56. Supply room I.
a) Steam kettle. 57. Bath,
In Extraction apparatus, 5S. Llbrarv.
ct Kilter press. 59.
<i < Press. BO—66. Dwelling
67—7(>. •' " of stoker.
inspector.
ei Evaporation table.
f) Scales. 71 —72. " " janitor.
g) Table.
semester 190.'5, i e. during the first year of the institute. For the
past year the attendance was 195 during the winter semester
1906—07 and 205 during the summer semester 1907.
That the instructional force was adequate to devote sufficient
time to individual students is shown by the list of names of the
staff of instructors for the year 1906—07. In addition to the
Director, Prof. Dr. Thoms, there were engaged in the Institute the
following scientists: the first assistant Prof. Dr. Traube, the

assistants Dr. G. Fender, Dr. C. Mannich, Dr. J. Herzog, Dr. A.
Schoenewald; the laboratory assistants Messrs. Lucius, Vogelsang,
Kuhn, Steinbach and Pries; the Private assistants Dr. J. Kochs,
Dr. T. Zernick, Dr. Nothack and Dr. Winter; in research work there
were also engaged the voluntary assistants Dr. Lenz, Dr. Richter,
Dr. Cusi and Dr. Banke.
During the same year the following courses of lectures were
given:
Prof. Thoms, Pharmaceutical chemistry: inorganic daring the winter
semester, organic during the summer semester.
The chemistry of foodstuffs and beverages, also urine analysis
during the summer semester.
Toxicological chemistry during the winter semester.
Prof. Traube — Chemical analysis during both semesters.
Prof. Gilg — Pharmacognosy.
Dr. Busse — Bacteriology for pharmacists.
First Floor.
78. Balcony. 90. Office of director.
74. Hydrogen HUlphide. Private laboratory of director.
75—78. Toilets fmd lavatories. 92. Koom for stenographer ami clerk.
79. Dark chamber. 93. Supply room II.
80—81. Balance rooms. 94. Elevator.
82. Conference room. 95. Cabinet for chemicals.
83—87. Corridors and stairways. 9fl. Lecture preparation room.
88. Quantitative analysis. 97. Large lecture room.
89. Organic chemistry. 98. Wardro e.
It should be stated that since the completion of the new Botani
cal Garden, the lectures in pharmacognosy are now given in the
recently completed Botanical Institute.
The Pharmaceutical Institute is, therefore, in reality an Institute
for Pharmaceutical Chemistry, the courses in physics and botany
being given in the respective institutes.
If the students preparing for the "Staatsexamen" are well pro
vided with space, equipment and instruction, the research student
is by no means forgotten. How true this is can best be shown by
a list of articles that have been published each year since the dedi
cation of the Institute.
PHA RMA CE I TICA t REVIEW. 7
These articles have been collected in the "Arbeiten aus dem

Pharmazeutischen Institut der Universitat Berlin" of which four
volumes have appeared thus far. Even after the present new struc
ture ha4 crumbled to dust, these volumes will stand a lasting
monument to the scientific spirit with which the Director and his
staff have entered upon their work. Four years are but a short
period, but they are full of promise for the future. May education
and research continue to go hand in hand, each stimulating the
other, and may they assist in the regeneration of our calling.
That equipment and methods are thoroughly modern, is possibly
best illustrated in the accompanying views of the machinery mounted
in the basement. While it is no longer to be expected that the
pharmacist prepare his own chemicals or even all of his galenicals,
it is important that he have some notion of the methods employed
in their manufacture. To this end he must not only visit large
laboratories but he must be given an opportunity to make typical
a a ojb ® 0
IB a B0 o El
Floor.
99. Hydrogen sulphide, 118. Elevator,
100—101. Toilets and lavatories, 114. nalance room.
102. rhiorlne. 11.1. Toxlcoloelcal analysis.
104. Volumetric analysis. 116. Private laboratory.
105-109. Corridors and stairways, 117. Balance room.
110. tjualltative analysis. 118. Cabinet.
111. Ether distillation, etc. 119. Small lecture room.
112. Supply room 111. 120. Large " "
examples of these preparations on a somewhat larger scale than is
possible with the ordinary laboratory equipment.
Chemical research, especially phyto-chemical research is equally
in need of such apparatus. The distillation of volatile oils, the
extraction of alkaloids on a large scale are essential to satisfactory
work. That the means for such work is provided is shown by the
accompanying cuts. That these means are put to good use is revealed
by the publications issued in the four volumes already referred to
For satisfactory plant chemical work an experimental gardt-n
has become as necessary as the machinery to work up the products
chemically. Such a garden is also provided. Indeed the grounds of
the Pharmaceutical Institute are but a part of the new large
PHARMACEUTICAL REVIEW.
Botanical Garden at Dahlem. The instructional vulue of such a

neighborhood, not to mention its aesthetic and sanitary advantages
will be readily appreciated.
Last, and it seems>'to me that I hear an echo of "not least"
from my colleagues on this side of the ocean, the Institute is ade
quately provided with janitors and others who in Germany are so
appropriately classed in the group of "Unterbeamten". In addition
to aisuperintendent of the building, there are a machinist, a stoker
and six janitors. That one of these janitors is sufficiently experienced
to act as a second lecture assistant goes without saying. That the
building is kept as neat and clean as is possible cannot be empha-
Third Floor.
121. AnalystH of colonial products. 125. Rulanre room.
122. '' " footl-tuffs and bever- 12i>. Photogrnphi«' room,
ages. . 127. Drus Cabinet.
12a. MkTOHOoplc room. 128. Corridor
124. Bacterlology. 129. Stairway.
sized strongly enough in the country where this aspect of the educa
tion of our youth is often neglected.
Now that the University of Berlin has at last recognized the
needs of the pharmaceutical student there is still hope for the other
universities. The idealsof the older generation of German pharma
cists, for a time at least, seemed shattered and internal strife and
commercialism seemed rampant. Now, however, the scientific spirit,
fostered in the modest building at Dahlem, shines once more like a
ii'uiding star. The calling that produced a Scheele and a Liebig
should never forget its traditions as a mother of scientists. E K.
Progress in Alkaloidal Chemistry during the Year 1906.'
Itv //. .1/. Gnrdm.
Metanicotine.
E. Maass and A. Hildebrandt find that when metanicotine is
reduced with sodium and absolute alcohol the product is not as
previously (Ber. 190"), 1831) reported hexahydrometanicotine but a
mixture of hexa- and octo-hydrometanicotine which can be separated
from each other by distillation with steam. The constitution of the
bases and their relation to metanicotine is shown by the following
formulas :
in. C11s HC CH2
en CH2
HC 0 _ i, H,.C
I hi; i:n2 | HC CH2
I ! I
HC CH NH.CHa HoC / CH- NH.CHa
N' Ml
Mettinlrotlne. He*uh vrtromftu nicotine.
<H2
CHs
I1..C CH
Hit' I'Hs
l2C Cll2 NHCHs
Ml
Octohyd romet anient iin'.
The octohydrometanicotine is identical with the octohydronicotine

previously obtained by Mian in the reduction of nicotine. The latter
compound though obtained from nicotine must also be looked upon
as a derivative of metanicotine for the leason that the octo com
pound boils at a temperature higher than the boiling point of nico-
* Cuntlnupd from Vol. 2", puRf 3(17.
tine but lower than that of metanicotine and it is well known that
reduced substances generally boil below the boiling points of the
substances from which they are obtained by reduction.
The metanicotine used for this work was obtained by a slight
.modification of Pinner's method (Ber. 1894, 1053). After reduction
with sodium and absolute alcohol the product was fractionally
distilled wi'th steam, the fractions of the distillate acidulated with
hydrochloric acid and, after concentrating to a syrup, the residue
spread on porous plates. Part of the thick liquid was absorbed by
the plates while another part remained as a crystalline powder. On
decomposing the crystalline powder with sodium hydroxide and
distilling the oily liquid which separated out the octohydrometa-
nicotine distilled over at 258.5—260°.
The porous plates were then powdered and extracted with hot
alcohol. After distilling off the alcohol, the residue was dissolved in
water and the liquid shaken out with ether after adding sodium
hydroxide. After removal of the ether and distilling the residue the
bexahydrometanicotine passed over at 248—250°.
Hexahydrometanicotine, C10H20N2, is a colorless oil boiling at
248—250°, having an odor like piperidine, becoming yellow on
standing and emitting vapors that irritate the respiratory organs.
It is easily soluble in alcohol or ether but insoluble in water. It is
optically inactive and at 20° has a specific gravity of 0.9578 com
pared with water at 4°.
The hydrochloride of hexahydrometanicotine, C1oH2oN2?2HCl is
a very viscous hygroscopic oil that cannot be obtained in crystalline
form. It is easily soluble in water, alcohol and chloroform, difficultly
soluble in acetone but insoluble in ether or ligroin.
A chloroplatinate of hexahydrometanicotine, C10H20N2.2HCl.PtCU,
was prepared by adding an alcoholic solution of platinum tetra
chloride to an alcoholic solution of the hydrochloride. It forms an
oily liquid which becomes solid when kept under absolute alcohol
but resin ifies on drying on porous plates. Recrystallized from hot
water it forms yellowish-red prisms melting at 225° with decompo
sition.
A chloraurate of hexhydrometanicotine could not be obtained in
crystalline form. It is precipitated from water as an oily liquid
which is soluble in alcohol but insoluble in water, acetone or ligroin.
PH A KMA CE VTICAL REVIK W. 11
Octohydrometanicotine, f'loHaaNa, is a colorless oil boiling nb

258.5—260° and having a penetrating odor. It is easily soluble in
water but separates out again on the addition of alkali. It is
optically inactive and at 20° has a specific gravity of 0.9173 com
pared with water at 4°.
A hydrochloride of octohydrometanicotine, C10H22N2.2HCl, was
prepared by adding hydrochloric acid to an aqueous solution of the
base and evaporating the liquid to dryness. It was purified by
treating it with acetone to dissolve resinous matter and recrystalliz-
ing from water. The salt is easily soluble in water, a little less
soluble rn alcohol- and insoluble ra ether, acetone or ligroin. It
melts at 202°.
A chloroplatinate, CioH2aNa.^HCl.PtCU, was mail© by treating
the alcoholic solution of the hydrochloride with an aleaholic solution
of platinum tetrachloride and rubbing up the oily double salt with
absolute alcohol. Recrystallized from water it forms dark red crys
tals melting at 202.5°.
A chloraurate, C10H22N2.2HCI.2AUCIa, was prepared by adding
an alcoholic solution of gold chloride to an alcoholic solution of
the hydrochloride and recrystallizing the double salt from dilute
alcohol. The chloraurate forms yellow leaflets melting at 142° with
out decomposition. It is soluble in ether and alcohol but insoluble
in water, acetone and ligroin. (Ber 1906, 3697.)
Mettaylmorphimethine.
According to R. Pschorr, H. Roth and F. Tannhiiuser a-methyl-
morphimethine is converted into /8-methylmorphimethine not only
by heating the former with potassium hydroxide in alcoholic solution
but even by heating the a-compound by itself in vacuum to about
220—240°. The identity of the ^-compound obtained by the authors'
method with the compound obtained by using alcoholic potassium
hydroxide was shown by a comparision of the benzonte and iodo-
methylate of which the former was made by boiling the ^-compound
with benzoic acid in solution in benzene and the hitter by digesting
the /3-compound with methyl iodide in benzene. The benzoate was
purified by recrystallizing it from a mixture of alcohol and petroleum
ether. The iodomethylate was recrystallized from water.
(I?er. 1906, 19.)
hHMlUAVKVTICAL 11EYIFAY.
Morphine. ■
J. C. Irvine finds that inactive lactic acid can be easily resolved
into the d- and l-acids by means of morphine, the morphine 1-lactate
crystallfzing quickly from dilute aqueous solutions while morphine
d-lactate crystallizes only after long standing in a vacuum desiccator.
By this method the yield of pure 1-lactic acid is almost quantitative
while the amount of lactic d-acid is about 50 per cent of theory. The
purity of the acids was established by the specific rotation of the
zinc salt and estimation of water of crystallization, but as the rota
tion of the metallic lactates display small rotations in solution the
purity of the acids was also tested by converting them into methyl
lactate and afterward into methylic methoxypropionate (Trans.
1899, 75, -1-8.")), which has a specific rotation of 95.21°.
The d- and 1-lactic acids were obtained by the zinc ammonium
salt method of resolution and the morphine salts prepared by neut
ralizing hot aqueous solutions of the acids with the alkaloid. The
morphine 1-lactate contains no water of crystallization and in 5 per
cent aqueous solution has a rotution [a]i>2(' = —91.8°.
The salt of the d-acid readily forms super-saturated solutions
and only crystallizes slowly in clusters of radiating prisms. It con
tains a molecule of water of crystallization and in 5 percent aqueous
solution has aspecific rotation ['']n20= —92.7°.
The inactive lactic acid used for resolution by morphine was
syrupy and contained 2.'i.2 per cent, of anhydride as was shown by
titration before and after hydrolysis. The acid was diluted to 8
times its volume with water and after boiling for six hours to
hydrolyze the anhydride the hot liquid was neutralized with mor
phine. On cooling the salt of the 1-acid crystallized out while the
salt of the d-acid remained as a syrupy liquid. The 1-acid was liber
ated from the morphine salt by ammonia and purified through the
calcium salt. From the calcium 1-Iactate the acid was set free by
oxalic acid and separated from traces of calcium oxalate by extrac
tion with a mixture of alcohol and ether.
The 1-acid was obtained as a colorless syrup and converted into
a zinc and a silver salt. By decomposing the latter with methyl
iodide a specimen of methylic l-lactate containing a small proportion
of methylic 1-methoxypropionate was prepared. By the method
previously described (loc. fit.) this was converted into methylic
l-methoxypropionate and found to possess a rotation of [«]i,-n =■
l'llMiUACElTWAL REVIEW.
94. 7°. The highest rotation recorded for this substance is [«]d20 =
+ 95.5°..;
In order to see whether the acid is not changed during the
methylation (Trans. 1901, 79, 972) the methylic 1-methoxy propionate
was warmed with hydriodic acid at the lowest temperature at which
in a Zeisel apparatus silver iodide was deposited ("85°) and, after
removal of the excess of hydriodic acid at 80° under reduced pressure
and converting the 1-acid into a silver salt by means of silver oxide,
the silver salt was decomposed by sulphuretted hydrogen and the
liberated 1-lactic acid converted into the zinc salt. Analysis of this
salt showed that no change in the configuration of the acid takes
place in the methylation. •
The preparation of d-lactic acid from morphine d-lactate was
carried out exactly as described in the case of the 1-acid. The d-acid
was analyzed as a zinc salt.
In connection with this work the author finds that although
active zinc lactate when crystallized in the usual manner readily
loses its water of crystallization at 110°, the residue left on evapor
ating an aqueous solution of the salt on the waterbath does not
become completely anhydrous even at 150°.
(J. Chem. Soc., 1906, 935.)
According to L. Georges and Gascard small quantities of mor
phine can be estimated colorimetrically by making use of the fact
that morphine liberates iodine from iodic acid coloring' the liquid
yellow or reddish-yellow. Addition of ammonia to the liquid changes
the color to yellowish-brown. The estimation is carried out by com
parison with solutions of morphine of known strength prepared
under identical conditions. (J. pharm. chim., 1906, 513.)
C. Mai and C. Rath have tried to make use of the color reactions
of morphine in order to devise a colorimetric method for the estima
tion of very small quantities of this alkaloid. The liberation of
iodine from iodic acid and the deep violet color given by Froehde's
reagent are not suitable for this purpose. Better results were ob
tained with Marquis' reagent which will detect 0.00003 gram mor
phine in 1 c. c. of liquid but the exact conditions for quantitative
work will be reported lateôn. (Arch. Pharm., 1906, 300.)
It. Pschorr finds that when morphine is digested with liquid
anhydrous hydrochloric or hydrobromic acid the alcoholic OH group
is replaced by CI. The products are therefore identical with chloro
14 PHARMACEUTICAL REViEW.
or bromomorphide previously obtained by Schryver and Lees (J.

Chem. Soc., 1900, 1092) by the action of the halides of phosphorus
upon morphine. In chloromorphide or bromorphide as well as in
chlorocodide and bromocodide (Ann., 210, 107; J. Chem. Sou., 1902,
563) the halogen is easily replaceable by radicals containing sulphur.
Thus with potassium sulphydrate a compound is formed which con
tains an SH group instead of chlorine. This compound is then
oxidized to a dimolecular compound as follows:
2CisH2»N02CI + 2KSH > [2Ci8H2»N02.SH] +0 > (CiBH29N02.S-)2
Chlorocodide. Btathiomorphide.
If instead of a sulphydrate an alkaline mercaptide be used alkyl-
thio derivatives are formed :
Ci8H28N02CI + NaSC2Hs = CisH29N02.SC2H5 + NaCl
Etbylthiocodide.
When the iodomethylate of chlorocodide is boiled with sodium
hydroxide both halogens ore split off and instead of the correspond
ing "methine" base, chloromethylmorphimethine, halogen free amor
phous products are formed. The chloromethylmorphimethine can be
obtained in the form of a hydrochloride by the action of phosphorus
trichloride upon a-meth.ylmorphimethine in chloroformic solution.
The decomposition products of chloromethylmorphimethine obtained
by boiling it with acetic anhydride are the same as those obtained
from a-methylmorphimethine, namely, acetylmethylmorphol.dimethyl-
oxethylamine and a base having the composition of tetramethyl-
ethylenediamine. The formation of acetylmethylmorphol from chloro
methylmorphimethine shows that in the decomposition by means of
acetic anhydride the alcoholic hydroxyl, not the indifferent oxygen
atom is eliminated, as in the latter case from chloromethylmorphi
methine containing a chlorine atom instead of the alcoholic OH
group there ought to be formed a chloroacetyhuethylmorphol. It is
remarkable that among the decomposition products of chloromethyl
morphimethine containing an N(CHa)a group there is found mono-
methyloxethylumine, HO.C2H4.NH.CHs. If phosphorus trichloride
be made to react with a-methylmorphimethine in the absence of a
solvent the product consists of the hydrochloride of the phosphorous
acid ester of methylmorphimethine.
If instead of phosphorus»4«shk»«d« pheepborua pentachloride be
made to react with a-methylmorphimethine a dichloride of methyl
PllAKMA CELTICA L REVIEW. 15
morphimethine, C1gH2sNOaClg, is formed which when decomposed

with acetic anhydride gives a derivative of trioxyphenanthrene
(diactoxymethoxyphenanthrene) together with the same bases that
are formed from chloromethylmorphimethine. The trioxyphenan
threne derivative contains an acetoxy-group linked to one of the
two "bridge" carbon atoms of phenanthrene as upon oxidation it is
converted into 3-methoxy-4-acetoxyphenanthrenequinone. Judging
from the identity of the melting points the diacetoxymethoxyphenan-
threne seems to be identical with the compound obtained by Knorr
in the decomposition of oxycodeine CI8HaoNOs(OH). The OH group
of the oxycodeine must therefore be at one of the "bridge" carbon
atoms.
The chloromorphide, C17H18NO2Cl, was prepared by digesting
morphine for several days at ordinary temperature with anhydrous
liquid hydrochlorie acid in an explosion tube, evaporating the acid
and after adding excess of sodium bicarbonate extracting the chloro-
morphide with ether. After recrystullizing from methyl alcohol it
melts at 192° (corr.). The yield is about 40 per cent, of theory.
The chloromorphide was converted into an iodomethylate by warm
ing it with methyl iodide. The iodomethylate melts at 207° (corr.).
Bromomorphide was obtained in the form of a hydrobromide by
treating morphine with liquid hydrobromic acid in presence of some
phosphorus tribromide. The hydrobromide melts at 196° with de
composition. The free bromomorphide can be easily obtained from
the hydrobromide. The yield is about 65 per cent. The bromomor
phide forms an iodomethylate melting at 200°'.
On digesting bromomorphide with phenyl isocyanate in chloro-
formic solution the corresponding ester of phenylcarbamic acid is
formed, showing the presence of an OH group.
The bisthiomorphide, (C18H29NO2.S—)2, was prepared by boiling
chloro- or bromomorphide with alcoholic potassium sulphydrate,
diluting with water and after saturating with carbon dioxide extract
ing with chloroform. The bisthiomorphide melts at 201°. When the
bisthiomorphide is methylated by means of sodium methylate and
methyl iodide it is converted into bisthiocodide iodomethylate. The
bisthiocodide underlying this iodomethylate can be prepared from
bromocodide (R. Fischer, Inaug. Diss., Berlin, 1903) by the same
method by which bisthiomorphide is made. The bisthiocodide is
soluble in alkalies and melts at 200°.
On treating bromocodide with ethyl mercaptan and sodium in

alcoholic solution while passing a current of hydrogen through the
solution ethylthiocodide is formed. The yield is about 90 per cent.'
Chloromethylmorphimethine could not bo prepared by treating
the iodomethylate of chlorocodide with sodium hydroxide, only
amorphous chlorine free products being obtained in the reaction. It
was iprepared by digest ing a-methylmorphimethine with phosphorus
trichloride in chloroformic solution at ordinary temperature in a
dry atmosphere and pouring the product into ether. The hydro
chloride formed in the reaction was purified by recrystallization from
alcohol and ether. It melts at 177—178°. The free chloromethyl
morphimethine could not be obtained in crystalline form. It was
converted into the iodomethylate by methyl iodide using acetone
and ether as solvents. The iodomethylate melts at 163° (corr ).
The hydrochloride of the phosphorous acid ester of methylmor-
phimethine, C19H22NO2.O. P(OH)2.HCl, ol.tained by treating a-methyl-
morphimelhine with phosphorus trichloride without using any sol
vent, has the same crystalline form and the same melting point as
the hydrochloride of chloromethylmorphimethine, C10H22NO2CI.HCl,
prepared from the same reagents in presence of chloroform as sol
vent. Even a mixture of the two compounds shows no change in
melting point.
The basic products obtained by heating chloromethylmorphi
methine with acetic anhydride differ according to the conditions of
the reaction. At a temperature of 170° under pressure the chief
product is methyloxethylamine, but if the heating is done in an oil
bath for a shorter time dimethyloxethylanine is obtuined. The bases
were identified as chloraurates. Another compound found among
the products of the last reaction is tetramethylethylenediamine.
If the chlorination of a-methylmorphimethine is carried out by
means of phosphorus pentachloride in chloroformic solution, methyl-
morphimethine dichloride, C1BH28NO3OI2,, is obtained. When treated
with methyl iodide in acetone solution the dichlorine derivative is
converted into an iodomethylate, C19H23NOaCl2.CH3l, which separates
out upon addition of ether. When heated with acetic anhydride the
methylmorphimethine dichloride yields the same decomposition pro
ducts as chloromethylmorphinjethine.
(Ber., 1906, 3130.)
PHA IMA CELTICAh REVINY. 17
Morphenol.
E. Vongerichten and 0. Dittmer have succeeded in converting mor
phenol into 3.4.5-trioxyphenanthrene by fusing the former with
potassium hydroxide, pouring the reaction product into water
acidulated with sulphuric acid and then passing a current of carbon
dioxide into the liquid. The precipitated trioxyphenanthrene is
purified by suspending it in water and shaking with ether and
separated from unattacked morphenol by shaking the ethereal
solution with very dilute sodium carbonate in which the trioxy
phenanthrene is easily soluble whereas the morphenol is .almost
completely insoluble in sodium carbonate. In pure water the trioxy
phenanthrene is considerably more soluble then morphenol. Con
centrated sulphuric acid colors it yellowish-red without any fluores
cence (difference from morphenol). Exposed to the air it gradually
assumes a dark gray color. On exposing an alkaline solution of the
trioxyphenanthrene to the air the solution soon assumes an intensely
yellowish-brown color.
The formation of the trioxyphenanthrene from morphenol can
be represented by following equation :
H0/*\
l 14
no
ho/
I !
I I !•
Morphenol, 8.4.5-trloxyphenanthrene.
Like phenanthrene, 'the trioxyphenanthrene is easily converted

(after acetylization) into an orthoquinone which has some similari
ties with morphol quinone but is not identical with it. Hence none
of the OH group of the trioxyphenanthrene is in the position 9 or
10 as in that case the quinone obtained from the trioxyphenanthrene
would be identical with morpholquinone.
in PHA RltA CEV TICA L RE VIEW.
110/ \
Morpholqulnone.
On heating the trioxyphennnthrene on the water bath for three
hours with methyl iodide in presence of sodium methylate in a
closed tube, evaporating the product and taking up the residue with
ether a trimethoxyphenanthrene was obtained in the form of an oily
liquid . It was purified by converting into a picrate by menus of an
alcoholic solution of picric acid and then decomposing the picrate
with ammonia.
The oxidation products of the tr.ioxyphenanthrene and its tri-
acetyl derivative could not be obtained in crystalline form.
(Ber. 1906, 1718.)
Mydriatic Alkaloid.
Ernst Schmidt and A. Kircher find that the seeds of that variety
of Datura fastuosa which is designated nor. ooernl. plen. contain
0.22 per cent, scopolamine and 0.034 per cent, hyosciamine whilst
those of the variety designated nor. alb. plen. contain 0.20 percent,
scopolamine and 0.023 per rent, hyosciamine. A small amount of
atropine is present in both varieties. Datura fastuosa is, therefore
not identical with Datura alba (comp. Shinoyama and Koshima,
Apoth. Zeit., 18!)2, 458).
Datura arborea obtained in the market was found to contain
scopolamine and hyosciamine in the proportion 1 :A. Another sample
of the plant grown in 'Marburg, several years old and gathered
when in flower, contained mainly scopolamine. A sample of a younger
plant gathered after it had flowered contained chiefly hyosciamine.
The root of this plant contained only a little hyosciamine.
(Arch. Pharm., 1!)06, 06.)
NOKTH W ESTERX U XIV EBHITY,
School of Pharmacy.
( To be continued. )
PHARMACEUTICAL REVIEW. 19
Historical Fragments.
By Edward Kremers.
14. Pharmaceutical Notes from Nuttall's Journal of Travels into

the Arkansas Territory.
Xuttall is probably best known to pharmaceutical students
through the abbreviation of his name occasionally found after the
scientific names of medicinal plants, such as Chimaphila umbellata,
Nutt., the prince's pine or pipsisewa. He was born, we are told, 1
in the market town of Settle, West Riding, Yorkshire, in 1786. His
parents being in humble circumstances, at an early age he was ap
prenticed to a printer. Discontent caused him to journey to London
and, at the age of twenty-two, to America, arriving at Philadelphia
in 1808.
In spite of the disadvantages under which he had labored, he
had been a student both of the classics and of the natural sciences.
In Philadelphia he met Dr. Benjamin Smith Barton, who stimulated
him in his botanical studies on which his reputation as a scientist
chiefly rests. Excursions in every direction were made. As a result
there appeared, in 1818, "The genera of North American plants and
a catalogue of the species to 1817."
In October of that year he started on a journey to the southwest
via Pittsburg and down the Ohio and Mississippi rivers to the Ar
kansas. Snring and summer of 1819 were spent in the Arkansas
territory where his chief work consisted in the collection of plants.
The record of this trip was published in 1821 2 and has recently been
republished as volume thirteen of the series of "Early Western
Travels."
The historical value of the account was the cause for its republi
cation in this series, and the general reader will be well repaid for its
perusal. However, while as a record of travel it is very interesting
i ThwaitcH: Early western travels, vol. 18, p. 11.
' A journal of travelH lutn the ArkuuHaH terrrltory during the year 1819. with
occasional observations on the mannerH of the aborigines IIIustrated by a map
and other ensrrnvlrg*, by ThomnH Nuttall, F L. S., honorary member of the Ame
rican HhiloHophieal Society, and of the Academy of the Natural Sciences, etc.,
Philadelphia, printed and published by Thos H. Palmer, \H2\.
20 PHA KMA CEUTWAL REVIEW.
reading, the writer was greatly disappointed in one particular. He

had hoped to find a pharmaceutical harvest equal to that gleaned
from the journals of the two Michaux. 3 While Xuttall shows re
peatedly that he is interested in the economic aspects of botany as
well as in systematic botany, he evidently cared little or nothing for
the medicinal uses of plants while on his journey.
Inasmuch as he did not expect to be taken ill, he did not provide
himself with medicine, so that when taken sick with the fever
(p. 266 2) he had to get along as well as he could with a substitute
for what he would otherwise have used.
His lack of interest in the medicinal uses of drug plants becomes
strikingly apparent on two occasions. Calling attention to the depi-
lation practiced by the Quapaws (p. 121), he states: "They employ
artificial means to eradicate that pubescence from their bodies, which
is, indeed, naturally scanty," but evinces no interest to learn what
depilatory agents are being used by them.
On another occasion (p. 189), while giving a rather detailed
account of the Cherokecs, lie relates the following observation:
"From some. cause or other, it appears that the women of the Chcro-
kees frequently made use of means to promote abortion, which at
length became so alarming, as to occasion a resort to punishment by
whipping." Here again any medico-botanical instincts that Xuttall
may have had remained dormant.
On still a third occasion he betrays the lack of interest in drugs
that might be expected of a modern therapcutic nihilist. He depicts
the sanitary conditions existing in New Orleans which made it possi
ble that over 5000 individuals should die of yellow fever in a single
summer. While calling attention to the shocking condition in the
hospital and the expense of medical assistance, not a word is said
about the character of the medical treatment or the use of drugs,
(p. 315.)
There are, however, a few gleanings on drugs to be recorded.
While on one of his botanical excursions he records (Feb. 3) : "I ob
served spring up, the Eryngium aquaticum, occasionally employed as
a medicine by the inhabitants, acting as a diuretic, and in larger
doses proving almost emetic." (p. 110).
On the same day he jots down another note of pharmaceutical
3 This journal, vol. 23, pp. 58 anil 80.
* Page references reter to the reprint.
PHA KMA CKITIC. I L KE VIEW. 21
interest: "The sweet gum tree (Liquidambar styraciflua) , which

produces no resin in the northern states, where it is equally indigen
ous, here, as in Mexico and the Levant, exudes the odoriferous Storax
of the shops." (p. 113.)
On the 28th of the next month, he refers to the culinary use
made of two drug plants in the following words: "The decoctions of
the wood of sassafras and spice hush (Laurus benzoin), which abound
in this country, are certainly very palatable substitutes for tea."
(p. 161.)
On August 14 th he records the practice of hunters relative to an
animal drug resorted to in the trapping of beavers: "Scarcely any
thing is now employed for bait but the musk or castoreum of the
animal itself. As they live in community, they are jealous and
hostile to strangers of their own species, and following the scent of
the bait, are deceived into the trap." (p. 2(>G.)
Although these gleanings are exceedingly meagre, it is apparent
that Xuttall thought, at least occasionally, of the medical practices
of both the aborigines and the early settlers, not a few of whom were
of a mixed breed. Further evidence of this we find in two statements
recorded by him relatively early during his wanderings through
Arkansas.
Having made the agreeable acquaintanceship oi a regular
physician, in "an insignificant village, containing three stores, desti
tute even of a hatter, a shoe-maker, and a taylor, and containing about
20 houses, after an existence of nearly a century," he adds, "such is
the nationality of these ignorant people, that French quackery has
hitherto been preferred to the advice of a regular physician."
Of the medical practice of the natives he records the following
general statement: "The cure of diseases, though sometimes at
tempted with rational applications, is not infrequently sought, among
the Quapaws. and many other natives of the continent, in charms and
jugglery."
Quite numerous, on the other hand, are his references to the
distribution and economic value of coal and salt and to the commerce
of the latter; to sugar and flour, to honey and buffalo tallow: and to
some of the features of "the hot springs of the Washita." (p. 282.)
Meagre though these gleanings are, they may, nevertheless, prove
serviceable to the future writer of the history of American drugs and
medicinal plants.
Assay of Fluidextract of Belladonna Leaves.
By A. H. Lyons.
The pharmacopoeial process for the assay of fluidextracts of the

mydriatic drugs gives in skillful hands fairly satisfactory results.
It has its difficulties, particularly when applied to preparations of
hyoseyamus, which contain an exceedingly small quantity of alkaloid.
The following alternative process is one I have settled upon myself
as the simplest and best.
Put into a 200 cc. measuring flask 20 cc. of solution of lead
subacetate (U. S. P.). Add 150 cc. of distilled water, mix and add
with constant shaking 20 cc. of the fluidextract. Make up with
distilled water to exactly 200 cc. Filter, using if necessary a double
filter, and returning the first portion of the filtrate until it passes
through quite clear. The filtrate should contain still some lead sub-
acetate; it is not desirable that the excess should be very huge,
and it may therefore be a better way to use at first only 15 cc. of
the lead solution, then after adding the water and the fluidextract
observing whether the mixture has any sweet taste, indicating that
the lead is in excess. If not, more of the lead solution should be
added, about 1 cc. at a time, until the sweet taste becomes perceptible.
The measure should then be made up to 200 cc. This in fact is the
method I usually follow.
When the filter has practically finished dripping, add to the
filtrate about a gram of granulated sodium phosphate, and stir
until the salt is dissolved. If the mixture still has perceptible sweet
ness, add more of the phosphate, until this is in slight excess. Allow
the mixture to stand at rest in a beaker a few minutes and test a
few drops of the clear liquid that will shortly separate with a little
sodium phosphate. If this produces any turbidity, add to the mix
ture more of the phosphate, until this is surely in slight excess. All
this takes but a few moments' time, although in the description
it may seem a complicated operation.
Filter once more, when the filtrate will be quite clear and almost
free from color. Transfer exactly 100 cc. of the filtrate, representing
10 cc. of the original fluidextract to a separator, add 25 cc. of
chloroform and about 2 cc. of water of ammonia. Shake carefully,
using a rotary motion. Generally there is no serious danger of
emulsification, but the possibility of such an occurrence must be
always borne in mind. Nearly the whole of the alkaloid will pass
into the chloroform in this first washing. Allow the chloroform to
separate completely and draw it off. Repeat the extraction with
two additional portions of chloroform, 20 and 15 cc. Evaporate
the chloroform in a tared beaker, dry on a water bath and weigh.
Then determine the alkaloid in the usual wny by titration.
The following is the routine method of making such titrations
which I habitually follow. I keep a carefully standardized deci-
normal sulphuric acid as the basis of the titration. Theoretically a
decinormal hydrochloric acid is perhaps preferable, provided this is
kept in a bottle with an accurately ground glass stopper and its titre
occasionally verified. I do not attempt to keep on hand a volumetric
alkali of .suitable strength (e.g. N/so or "/as) for titrating alkaloidal
residues. Instead, I use a solution prepared extem poraneously, and
only approximately of the strength preferred. Until lately, my practice
has been to keep on hand a solution of potassium hydrate of approxi
mately "normal" strength, containing a little barium chloride to
keep it free from carbonate. When I had occasion to make a titra
tion, 1 would put 2 cc. of this solution into a 50 cc. measuring flask
and fill it up to the mark with distilled water as free as possible from
carbon dioxide. In place of this 1 am now using preferably Mme water
diluted with an equal volume of pure distilled water. In either case
the detail of the titration is the same. It is conducted as follows:
The alkaloidal residue is dissolved in 2 cc. of alcohol. To the
solution is added 2 cc. of decinormal sulphuric acid, 20 cc. of distilled
water and 5 drops of cochineal indicator. Into a small fiask is
introduced at the same time 2 cc. of the same alcohol, 2 cc. of the
decinormal acid. 20 cc. of the same distilled water and 5 drops of
the same indicator. Alkali (lime water or potassium hydrate solu
tion) is then added from a graduated pipette until the color changes.
The amount of alkali consumed is read off, 2 cc. more of acid is
added and the titration repeated. The two results will exactly cor
respond unless by any chance the alcohol or the distilled water used
were not strictly neutral — a possibility always to be kept in mind
in these delicate titrations. The second titration in any case gi1es
us the exact strength of the alkali we are using. If it differs from
the first, we may still go on with the determination, since we know the
exact amount of the error due to imperfect neutrality of our solvents.
The next step is to titrate the alkaloidal solution, noting the
exact amount of alkali required to neutralize the excess of acid. We
have now all the data for our calculation. We subtract the amount
of alkali consumed in neutralizing excess of acid in the alkaloidal
24 PHA KMA (JK UTICA L Ki: I IEW.
soltition from the amount consumed in the first blank experiment.

The difference gives the alkalinity of the alkaloidal residue in units
whose value is easily reduced to the "normal" standard. Suppose,
for example, that we have found our alkaloidal residue to be the
equivalent of 4.55 cc. of our "standard" alkali, and that we have found
(in our second blank titration) that 2ec. of decinorrr.al acid require for
neutralization 7.45cc. of our "standard "alkali (i. e. Icc. of decinormal
acid •corresponds with 3.725 cc'. of the "standard" alkali). Then
4.55 -f- 3.725 = 1.22 + cc. will be the quantity of decinormal alkali cor
responding with the alkaloid present, and since each cc. of decinormal
alkali corresponds with 0.0287 gm. of atropine, our residue contained
1 22 X 0.0287 -= 0.035 + gm. of alkaloid estimated as atropine.
The calculation reduced to the form of a "rule" is very simple.
Subtract the result of the final titration expressed in cubic centi
meters from the result of the first blank titration, multiply the
remainder by 57.4 and divide the product by the result of the second
blank titration. The quotient will he the quantity of atropine
present, expressed in milligrams. Fluidextract of belladonna root
or of stramonium would be assayed in exactly the same way as the
fluidextract of belladonna leaves. For the assay of tincture of
Belladonna or Stramonium, take 100 cc. of the tincture, evaporate
to about 25 or 30 cc., treat with 10 cc. of solution of lead sub-
acetate, after making up to 85 cc., add distilled water to make up
exactly 100 cc. and proceed substantially as above described, using
finally for the assay the equivalent of only 50 cc. of the tincture.
For the assay of Fluidextract of Hyoscyamus, use 25 cc.
each of the lead solution and the fluidextract, make up o
250 cc. and take of the filtrate 125 or preferably 150 cc. In my
experience the alkaloid is taken out more readily from this dilute
solution than it is in the pharmacopoeial assay process, and in a
condition much better suited for titration in that it is nearly free
from color. The quantity of chloroform required is not materially
greater than in the process first described, 30, 25 and 20 cc. being
sufficient. For the assay of the tincture of Hyoscyamus, it is best
to take at least 2('0 cc., evaporate to about 50 cc., dilute with
water to 175 cc., add solu ion of lead acetate 20 cc. (or q. s.) and
make up with water to 200-ec. I prefer myself to use the whole of
the filtrate, but those who are not quite at home in mathematical
calculations will prefer to use a definite aliquot port — 100 or 125
cc., although this quantity will represent only 10 or 12.5 grams of
hyoscyamus. The remaining details of the assay are to be carried
out exactly as described above.
7'11 Ml 1/1 CELTICA L REVIEW. 2.">
.1
Literary.
Books Reviewed.
La pharmacie en Poitou jusq'u a 1'an XI. Par Pierre liamhaud.
Tome trentieme (deuxieme serie), annee 1!)0<>, de Bulletins et
M<5moires de la Soeiete des Antiquaires de l'Ouest. Poitiers.
1907.
This monograph of eight hundred pages and eight plates is the
result of nine years of activity on the part of its author and caps
the climax of what has thus far been accomplished in recent years
by French writers of monographs of local pharmaceutical history.
Let us briefly review the situation. It is little more than half a
century ago that the comico-classicol "l'Histoire de la pharmacie"
was published by Philippe in 1853. It remained the only French
work of its kind until the "l'Histoire de la pharmacy" by Andre-
Pontier was published in 1900. The studies of Grave and Gilbert
do not fall into the same category. Valuable as are the work of
Andre- Pontier and similar attempts, they have been useful above all
in demonstrating that the time was not ripe for writing a general
history of pharmacy, nor even a pharmaceutical history of a single
country. Thanks to the indefatigable work and inspiration of the
Librarian of the ficole SupeYiure de Pharmacie at Paris, it has be
come fashionable in France to study and write up the pharmaceuti
cal history of a single locality. Such local monographs have
appeared for Mordeaux, Lille, Avignon, Bourgogne, and now for
Poiton. All of these are based on the study of local documents and
institutions.
Although a monograph of eight hundred pages seems rather
formidable as a local history of a single calling, we yet welcome it
as a manifestation of a spirit rightly directed. It may be regarded
as another extreme when compared with the intuitive effusions of
Philippe, but these monographs, no matter how voluminous, will
some day be utilized by a master mind who will write a history of
pharmacy in France such as was an impossibility before these
monographs existed.
However, these monographs are not only useful as stepping-
stones, they certainly must imbue French pharmacy with an idealism
that is sadly needed in this age of commercialization. Slill more,
their contents are by no means devoid of interest though largely
documentary. It may be regarded as a trifling matter that the

French spelling of the word apothecary was "apoticaire" in 1420,
and "appoticquaire" in 1480 in the same community, yet to the
philological student documentary evidence of this sort is as valuable
for one word as it is for another.
However, the volume is by no means composed exclusively of
reprints of documents: — "Contract of apprenticeship in pharmacy,
March 10, 1617 (from the minutes of a notary at Poitiers); Letters-
patent granted by Francis Z to the apothecaries at Poitiers, June
18, 1541 : Extract from the inventory of David Helie, master apoth
ecary of Poitiers, made April 10, 1656; etc." These documents
cover but one hundred pages. By far the largest portion of the
volume is devoted to a description, in minute detail, of all that
pertains to the history of pharmacy of that community. Thus, the
first chapter is devoted to pharmacy as practiced by the monks in
the monasteries; the second chapter to the private apothecary of
the higher nobility in which we learn incidentally that he was given
the nineteenth place in the household of Louis II de la Tremouille
in 1484. He was placed after the barber, the valet de chambre
etc. The two chamber maids and the nurse are the only ones whose
pension is smaller than his. In the third chapter we are introduced
to the first spicer-apothecaries in the twelfth and thirteenth centuries,
the precursors to the independent apothecaries proper. Every detail
of the apothecary's life is discussed: his apprenticeship, his "Wan-
derjahre", his studies, his examination to mastership, his establish
ment as apothecary, his work in the "officine", his social status.
In like manner the apothecary shop is treated: "The equipment of
a pharmacy, its inspection" etc. Other aspects of pharmaceutical
activity are discussed in the chapters devoted to "The apothecaries
and the reformation''; "The commerce in drugs at Poitou" ; "The
practice of pharmacy by the widows of the apothecaries"; "The
illegal practice of pharmacy by surgeons, druggists, and spicers";
"The practice of pharmacy by charlatans'"; "Apothecaries as writ
ers"; etc.
We welcome this new monograph in the same spirit with which
we have greeted its precursors. There can be no doubt but that
others will follow anil that before a generation has passed the local
history of French pharmacy will be available to historians to a
degree totally unknown in any other country. E. K.
Mt'SEUM Report. A series of notes on donations to the Museum

and Herbarium during the years 1903—6, compiled by E. M.
Holmes, Curator of the Museum. Brochure, pp. IV, 83. The
Pharmaceutical Society of Great Britain. 1907.
In the year 1895, the Council authorized the publication of the
first Museum Report. . This seemed desirable, not only because of
the large number of donations received, but also because the work
of the Curator resulted in no small amount of information, concern
ing foreign drugs and medicinal plants, that seemed of sufficient
practical value to justify its publication in convenient form. This
first report covered the years 1893—4. A record report covering
the years 1895—1902 was published in 1903. A third report, cover
ing the last three years, viz. from 1903—6, has only recently made
its appearance.
Whereas, in the second report the Curator states that "the in
formation .... obtained in some cases has proven to be of scientific
rather than of immediate practical value, and has not. been deemed
suitable for publication in the Journal of the Society", the pn sent
report is almost entirely made up of reprints from ''The Pharmaceu
tical Journal." Iu their present form the articles become an inter
esting record of the growth of the Museum and more particularly of
the activity of the Curator. Those who have had an opportunity
to see this museum can appreciate the enormous amount of work it
represents. It is a pity that the space devoted to it cannot be
trebled and that the general public does not share more in the
benefits to be derived from such a collection. Especially at the time
when pharmacy tends so strongly towards commercialization, a
public educator, such as a museum of drugs might well be, would
offset, to some extent at. least, the belief that druggists are to be
regarded as mere vendors of drugs as they are mere salesmen of
toilet and sundry other articles. E. K.
A Manual of Materia Medica, especially designed for students of

pharmacy, by Edsel A. Ruddiman. Lea Brothers &
Co. New York. 1907.
The author has provided a manual which is very suggestive in
size and general make-up of the well known materia medica of Maisch,
except that there are no illustrations. In about 420 pages the whole
field of materia medica, including vegetable and animal drugs, acids,
salts, organic and synthetic compounds, alkaloids, neutral principles
and oils, is condensed, the author believing that a systematic
arrangement of facts makes them easier to memorize.
The order of study of vegetable drugs is nearly that of Culbreth's
materia medica. When taken up in the manner given in Culbreth
28 PllA KMA CE I TICAL KEY IE W.
this arrangement is very satisfactory and instructive, but when

taken up in the manner given in the manual the arrangement has
absolutely no significance. In Culbreth the drugs are arranged
according to a natural botanical system of classification and each
group of plants is preceded by a concise description of the botanical
characters of the plants comprising that group. In Ruddiman's
book there is not the faintest suggestion of division into groups
and the value of such a grouping is entirely lost to the student.
This method in a book in which memorization of condensed facts is
the role, is hardly to be commended. The same may be said of
the order of the organic and synthetical drugs. Even the student
who has had the regular course in organic chemistry might be be
wildered by the sequence in which the materials are considered.
With some exceptions the text harmonizes with an important
part of our present knowledge of the materials mentioned. In con
nection with a course of lectures and demonstrations this book be
comes valuable and for this purpose is commended. It is also of
value in preparing for state examinations. The mechanical construc
tion of the book is excellent. ./. O. Schlotterbeck.
Phaumaknostischeb Phaktikum. Kine Einleitung zur mikroskopischen

Untersuchung von Drogen and Drogenpulvern, zum Gebrauche
in praktischen Kursen der Hochschulen, von Dr. Ludwig
Koch and Dr. Ernst Gilg. Mit 140 Abbildungen. Verlag
von Gebriider Borntraeger. Berlin. 1907.
Since this volume is an enlargement, both in size and scope, of
Koch's '"Einfuhrung in die mikroskopische Analyse der Drogenpulver,'"
the reader is referred to the review of that book given in this journal
Vol. 25, page 27—29. In the former work the student was led
directly into the study of the drug in its powdered form. In this
book the consideration of each powdered drug is preceded by the
histological study of the crude, unpowdered drug. Dr. Ernst Gils
has prepared this portion of the text while Dr. Ludwig Koch is
responsible for the text pertaining to the powdered drug. The writer
of this review has always considered the method adopted in the
newer book to be the only rational method of studying drugs and
their powders. The structural fragments in a powder never have
their full significance to the student unless he possesses a knowledge
of the normal unbroken elements in the crude drug obtained by
razor sections or knife scrapings. The study of drug powders in
dependently is rather unsatisfactory and is like putting the cart before
the horse.
PHA tillACE UTICAL REVIE W. 2'J
In the former book but 37 drug powders were discussed, in the

new book 78. The former contained 49 original illustrations, the
latter 140. The new volume contains 100 additional pages.
The former volume was highly recommended to all interested in
this line of study. The present enlarged volume is much more valu.
able and should certainly be found in every working library upon
this subject. J. 0. Schlotterbeck.
Manual of Physiological and Clinical Chemistry, by E. H.

Bartley. P. Blakiston's Son & Co., New York. 1907.
This little manual of Professor Bartley 's embodies an idea, cur
rent among a steadily decreasing number of physicians and teachers,
that a man should be taught only what he is likely to need later in
his profession, without regard to the laying of a solid foundation
of scientific knowledge upon which to rest the superstructure of
clinical tests and short cut methods of a pseudo-scientific character.
Within the two hundred odd pages of the volume, the author has
undertaken the truly difficult task of teaching the rudiments of
physiological chemistry, quantitative analysis, chemical and clinical
examination of the blood, gastric contents, urine, feces, and milk.
From time to time he adds excursions into more special fields, from
Cryoscopy with the theory and technique of the molecular lowering
of the freezing point, to a short course in the modification of cows'
milk for infant feeding. Turning the pages at random we quote a
few of the many topics touched upon, the better to convey an idea
of the apparent scope of the work: "Exercises in Experimental
Physiological Chemistry", "The Examination of Artificial Foods",
"Clinical Examination of Blood", "The Balance", "Measuring Instru
ments", "Diagnosis of Renal Diseases", "Chemical Analysis of Gall
Stones", "Umikoff Reaction" (for human milk), "Qualitative Experi
ments with Milk" (a series of seventeen very superficial reactions),
"Detection of Impure Water in Milk", etc., etc. The book is rich in
tests for this and tests for that, but devoid of the fundamentals of
physiological chemistry upon which these tests depend. For example
in the section devoted to carbohydrates we find a description of
Fehling's tests for the Hexosee, with no explanation of the reaction,
no indication of the particular groupings in the molecule that render
the reaction possible, nor suggestion that many other aldehydes
give the identical result. Even the empirical formulae given are not
reliable, for in this same section we find the Pentoses figured as
CbH1oOs.
Obviously any such volume is far from being devoid of worth.
Even so heterogeneous a combination of physics, chemistry, clinical

diagnosis, and food analysis as this may have a very useful place.
That place is not, however, in the early instruction of the coming
medical men of this country. The trend of our leading schools and
foremost teachers is for broader and deeper foundations, not for a
handful of empirical tests. If the clinician has a thorough under
standing of the principles of chemistry, physics, and physiological
chemistry, the routine reactions of his clinical examinations have a
significance, an elasticity of application, a resourcefulness, that the
man brought up on the rule of thumb method exemplified by this
manual can never acquire. Until a man has passed beyond the stage
where he has to be told what a balance, a standard solution, or a
proteid, is, he is hardly in a position to deal intelligently with the
"Diagnosis of Henal Diseases".
Tne appearance therefore of a manual of this character, with its
extreme superficiality of treatment, cannot be welcomed by us with
unlimited enthusiasm, nor can its use in the class room be recom
mended. As a text book for medical students it is in no way an
advance. There are several such on the market of greater merit. If
on the other hand a physician or teacher desires a ready reference
volume where he can turn to some forgotten test or desired formula
— like Uarfoed's test for dextrose, or Ewald's Test Breakfast — this
is as good as or better than any volume of its size and weight with
which we are familiar. H. C. Bradley.
MeDIZINISCH-CHEMISCHE I'.NTERSUCHUNGEX FUR APOTHEKER, VOI1 Dr.

W. Lenz. Julius Springer, Berlin. 1907. M. 3.60.
This little volume is of much less pretense and greater worth
than the preceding. As its title suggests it is designed especially for
pharmacists who are required to make clinical and chemical exami
nations of urines, feces, blood, and stomach-contents. The chapters
on these subjects are concise, accurate, and discriminating. They
give more real chemistry than is to be found in many larger and
more complete works, and are addressed evidently to men who
already have the ground work of analytical chemistry at their dis
posal. In the chapter on urine analysis, for example, the reactions
for all the normal and many of the pathological compounds are
given with the best methods for their quantitative estimation. In
.selecting only a few of the most reliable tests, and detailing one or
two of the most effective methods for exact estimation, much of the
useless lumber which encumbers the older and fuller treatises on this
subject is eliminated. At the same time each method is given in
PHA RMA CELTICA L REVIEW. .11
thorough detail, with an example to illustrate the method of cal

culating results, preparation of standard solutions, and other useful
information. At the same time enough of the chemistry involved is
explained and formulae given., so that a very fair knowledge of the
processes involved may be had. We can therefore recommend the
book, not only to technical chHmists who have occasion to make
clinical examinations, but to physicians and teachers as well, as an
up to date, handy collection of well selected, reliable reactions and
methods of analysis. It is the kind of book that is made for a
definite purpose, meets the purpose well, and will not lie idle on a
bookshelf. H. C. Bradley.
An Introduction to Vegetable Physiology. By J. Reynolds

Green. Second edition. Philadelphia. P. Bin kiston's Sons
& Co. 1907. Pp. xx + 4o9. 182 illustrations.
A revision has just appeared of this textbook, the first edition
of which was published in 1900. The original work was the result
of a successful endeavor to write an introduction to the subject of
plant physiology, "which, while putting physiology into its proper
prominence among the branches of botanical study, shall serve to
pave the way of the student and of the general reader to the more
complete discussion of the subject which may be met with in the
advanced textbooks of Sachs, Vines and Pfeffer."
Before the publication of this book, there was no elementary
textbook in English devoted to vegetable physiology, nor is there
yet in any other language one which meets exactly the same needs.
It is not surprising that the work was well received upon its first
appearance, nor that the demand has justified a second edition.
The reader is disappointed to find so little change, in view of the
great activity in certain departments of physiological investigation
in the past seven years. The oaly considerable change in the order
of treatment of topics consists in removing the discussion of respira
tion from its former place, in close relation with the aeration of
plants, and incorporating it with the chapter on the energy of plants
— a change which constitutes a marked improvement.
The treatment of the factors concerned in producing the trans
piration current, unsatisfactory as it was in the former edition, is
still more so now because of the author's failure to take cognizance
of the results of recent investigations. The importance of root
pressure in this connection is, as before, much exaggerated. The
relations of evaporation and osmosis to transpiration are discussed
in a very illuminating way ; but sufficient emphasis is not laid upon
the great force that, as has been lately shown, osmotic pressure
may exert in the leaves; and there is no mention of the importance
of the cohesive power of a column of water as a factor upon which
the existence of the transpiration current depends.
The description (in the chapter on reproduction) of the phenomena
of nuclear and cell division is both inadequate and inaccurate, and
betrays the author's unfamiliarity with the present state of know
ledge concerning this fundamentally important division of his subject.
Throughout the other chapters, the treatment is on the whole a
happy one. The style is admirably lucid and adapted to the needs
of elementary students; though the author's desire for clearness of
exposition has in some cases led him into rather too great freedom
of repetition, and in others into dogmatic statements concerning
matters which are really far from settled. In the latter respect, it
is conceivable that the pedagogical value of the volume might have
been increased by displaying rather than hiding the gaps in our
knowledge, in the hope of stimulating an occasional student to
further inquiry.
There has been no improvement in the illustrations, of which,
though many are excellent, many others are extremely crude or
actually misleading and could easily have been replaced by much
better figures. Possibly the undue economy shown in the retention
of antiquated drawings is to be blamed to the publishers. A similar
economical turn has led in many cases to the repetition of the same
figure in different connections — not necessarily a fault if occasionally
resorted to with good reason, but here appearing so often as to be
really amusing. Twenty-three figures occur each in two places in
the volume, usually to illustrate two very different points; eight
are used three times each, one four times, and one makes no less
than seven appearances. By the free use of this device, a relatively
small number of cuts may be made to produce upon the casual
reader an impression of lavish illustration.
As in the earlier edition, the entire lack of bibliographical
references is a serious defect. C. E. Mien.
ERRATUM.
Throughout Dr. Lyons' article, Some New Alcohol Tables, p. 353 of the
December Review, for Alosley read Morlfijr.
Volume 26. FEBRUARY, 1908. Number 2.
Progress in Alkaloidal Chemistry during the Year 1906*
By H. M. Gordin.
Oxycodeine.
L. Knorr and W. Schneider have investigated the compounds
obtained in the exhaustive methylation of oxycodeine which, to-
together with codeinone, had been previously obtained by Ach and
Knorr by oxidation of codeine (Ber. 36, 3067). As has been shown
by Knorr (Ber. 36, 3074) codeinone resembles thebaine in the be
havior towards reagents, both giving thebenine when treated with
dilute hydrochloric acids and morphothebaine when treated with
fuming hydrochloric acid. Boiling acetic anhydride converts both
into ethanolmethylanine and 3-methoxy-4.6-dioxyphenanthrene. Oxy
codeine on the other hand behaves towards reagents like codeine.
With acetic anhydride oxycodeine gives a diacetyl compound which
is hardly affected by boiling acetic anhydride at 180° and the products
obtained in the exhaustive methylation of oxycodeine are analogous
to those obtained in the same reaction from codeine, the latter being
converted into a-methylmorphimethine which is decomposed by
acetic anhydride, while oxycodeine is converted into oxymethyl-
morphimethene which is also decomposed by acetic anhidride into
ethanoldimethylamine and methyldiacetyltrioxyphenanthrene, C14H7-
(O.CH.s)(O.CHa.CO)2- This compound being derived from oxycodeine
must be different from the 3-methoxy-4.6-diucetyldioxyphenanthrene
obtained by the action of acetic anhydride upon codeinone. In the
same way the trioxyphenanthrene underlying the methyldiacetyl-
trioxyphenanthrene derived from oxycodeine, containing the new OH
group which enters the molecule in the oxidation of codeine to oxy
codeine, cannot be identical with the trioxyphenanthrene which
underlies the 3-methoxy-4.6-diacetyldioxyphenanthrene obtained from
codeinone and which must contain the alcoholic OH group of codeine
but no new OH group. As the yield of oxycodeine is very small no
thorough investigation of the trioxyphenanthrene derived from it
* Continued from page 18.
(33)
could be made, but from the facility with which the new OH group
enters the reduced part of the codeine molecule the conclusion is
drawn that this OH is attached to a tertiary carbon atom of the re
duced phenanthrene, i.e., to the same carbon atom to which is attached
the nitrogen containing side ring of the "morphium" alkaloids.
The oxycodeine used in this investigation was analyzed as a
picrate and a picrolonate. The picrate separates out in an oily
condition from a hot saturated aqueous solution, but on slow cooling
it crystallizes in prisms. The picrolonate is formed on mixmg the
components in alcoholic solution and separates out as an oily liquid
which soon bpcomes crystalline.
Oxycodeine iodomethylate hail been previously prepared by Ach
and Knorr using ethyl alcohol as a solvent and found to contain
half a molecule of alcohol of crystallization. The authors prepared
it by boiling oxycodeine with methyl iodide using methyl alcohol as
solvent and found it to contain one molecule of methyl alcohol of
crystallization.
Oxymethylmorphimethine, C10H23NO4, was prepared by boiling
oxycodeine iodomethylate with strong sodium hydroxide and extract
ing the aqueous liquid with ether. Upon slow evaporation of the
ether the oxymethylmorphimethine separates out in crystals which
contain ether of crystallization and melt between 50—00° losing the
ether and becoming syrupy. On exposure to air the crystals lose
their ether of crystallization and become sticky.
Oxymethylmorphimethine dissolves in concentrated sulphuric acid
with a yellow color which disappears upon dilution with water. In
this it differs from oxycodeine and the four isomeric methylmorphi-
methines which all give with cold sulphuric acid characteristic color
reactions. When the yellow solution of oxymethylmorphimethine in
sulphuric acid is gradually warmed it assumes a raspberry red color
till the temperature rises to 60° when the red color again disappears.
A hydrochloride, a picrate and a picrolonate of oxymethyl
morphimethine were prepared and analyzed.
When oxymethylmorphimethine is heated to 100° with alcoholic
potassium hydroxide (10%) a compound is formed which melts at
130° and forms an iodomethylate of a very high melting point
(about 300°). The compound differs from oxymethylmorphimethine
in that it dissolves in sulphuric acid with a violet-red color which
upon addition of water passes through blue-violet into green. These
PHARMACEUTICAL REVIEW. :ir>
properties of the compound would seem to indicate that it is not

au isomeric oxymethylmorphimethine as was supposed at first but
is identical with /3-methylmorpl'imethine.
On warming oxymethylmorphimethine on the water bath with
acetic anhydride, decomposing the excess of the anhydride by pouring
the solution in hot water, adding an excess of sodium carbonate
and shaking out with ether, diacetyloxymethylmorphimethine was
obtained in crystalline form. The diacetyl compound behaves to
wards sulphuric acid exactly like oxymethylmorphimethine. It forms
an iodomethylate melting at 260° when treated with methyl iodide
in methyl alcoholic solution.
On treating oxymethylmorphimethine with methyl iodide an
iodomethylate was obtained which crystallized from water with 1%
molecules of water of crystallization which is not removed in desic
cator.
On boiling oxymethylmorphimethine with acetic anhydride it is
decomposed into a basic substance, ethanoldimethylamme, HO.CH2.-
CH2-N(CH3)2, and a nitrogen-free compound, methyldiacetyltrioxy-
phenanthrene. The ethanol dimethylamine was isolated in the form of
its characteristic chloraurate. The methyldiacetyltrioxyphenanthrene
was purified by washing its ethereal solution successively with dilute
sodium hydroxide and dilute sulphuric acid and then recrystallizing
repeatedly from alcohol. It melts at 201° (the isomeric ;i-methyl-
4.6-diacetyltrioxyphenanthrene obtained from codeinone melts at
162-163°). (Ber. 1906, 1414.)
L. Knorr continues his investigations of the morphium alkaloids.
In a previous paper (see preceding paragraph) it was shown that
oxymethylmorphimethine obtained from oxycodeine can be decom
posed by acetic anhydride into ethanoldimethylamine and methyl-
diacetyltrioxyphenanthrene. This phenanthrene derivative must have
the same relation to methylacetylmorphol obtained from codeine as
oxycodeine to codeine, i. e., the methyldiacetyltrioxyphenanthrene
obtained from oxycodeine still contains the OH group (in the form
of an acetoxyl group) which is introduced into codeine upon oxida
tion with chromic anhydride.
When this methyldiacetyltrioxyphenanthrene is oxidized methyl
acetylmorphol quinone of known constitution is obtained. The
tertiary alcoholic OH group introduced into codeine when it is con
verted into oxycodeine is therefore destroyed in the oxidation of the
methyldiacetyltrioxyphenanthrene to the quinone. Hence this OH

group must be in position 9 or 10 of the phenanthrene nucleus and
the two carbon
CHs.O/ 2 \ CHs.O/
is 1t
4 1 I I
CHsCO.O\ /\ CH3C0.0\ /\
CrOs V Vo
{„■CHsCO >
\
Methyldlacetyltrioxy- Methylacetylmorphol-
phenanthrene from oxycodeine. qutnone.
atoms which form the "bridge" in the phenanthrene molecule must

be present in the form of CH groups in codeine and in methylmor-
phimethine. It follows from this that neither Freund's formulae for
thebaine and codeine (Ber. 1905, 3234; 1906, 844) nor Pschorr's
formula of morphine (Ber. 1902, 4382) are correct. (In Freund's
formula for codeine the "bridge" is unsaturated, in Pschorr's formula
the "bridge" in codeine is dihydrated but in methylmorphimethine
it is unsaturated.)
CH.h.O/ /\
CI I ,.o/\
/ \/ N
°< |cH \/ \H2
\ .A
°< H|
CH \
\N.CH3
% H
I N II
HO.HC\ /CH HO.HC\ /\ /CH»
^CH^ V
Ho \/CH2
Codeine Codeine
(FreuniPs formula). (Pschorr's formula).
PHARMACEUTICAL REVIEW. a7
CHs.O
11
! HI
IIO.HC\ / —CH2.CHa.N(CHs)2
II
Methylmorphimethine
(PHchorr'H formula).
If Freund's formula for codeine were correct both oxycodeine and
oxymethylmorphimethine ought to have phenolic character. Accord
ing to Pschorr's formula at least oxymethylmorphimethine ought
to have phenolic character. As neither of these compounds behave
like phenols these formulas cannot be correct.
The oxidation of methyldiacetyltrioxyphenanthrene was carried
out by means of chromic acid in glacial acetic acid solution accord
ing to Vongerichten's method (Ber. 1898, 52). A comparison of the
resulting methylacetylmorpholquinone with the methylacetylmor-
pholquinone obtained from methylacetylmorphol showed that both
were identical. (Ber. 1906, 3252.)
Piperidine.
On comparing the oxidation velocities of diethylamine and piperi
dine Th. Wallis found that the latter is so much more easily oxidiz-
able than the former that the difference could not be explained by
the cyclic structure of piperidine. It must be assumed that even the
best grade of commercial piperidine contains some partially reduced
pyridines which are much more easily oxidizable by potassium per
manganate than piperidine and that these impurities act like oxygen
carriers causing the rapid oxidation of the hexahydro base. If
piperidine be purified by converting it into nitroso-piperidine the
impurities can be removed by subjecting the nitroso compound to
the action of potassium permanganate in acetone solution. Under
these conditions the impurities are easily oxidized and separate out
together with the manganese dioxide in form of potassium salts
whereas the piperidine, remaining unattacked, can be recovered by
PllA KMACEUTICAL REVIEW.
decomposing the nitrosamine with hydrochloric acid and distilling

the piperidine hydrochloride thus obtained with potassium hydroxide.
Purified by this method piperidine has the same physical properties
as ordinary piperidine but differs from the latter in being unaffected
by potassium permanganate in alkaline solution.
The presence of partially reduced pyridines in ordinary piperidine
is also shown by the fact that the acetyl derivative of ordinary
piperidine quickly absorbs bromine in aqueous or chloroformic solu
tion whereas the acetyl derivative of piperidine previously purified
by the method describee! above hardly reacts with bromine even in
the course of an hour.
Attempts to purify piperidine by treating it with sodium and
boiling alcohol so as to convert the partially reduced pyridines into
piperidine were not successful. The product had the same oxidation
velocity as the original piperidine.
Another attempt to purify piperidine was made by treating it
with benzol sulphochloride in alkaline solution, subjecting the benzol
sulpho compound to fractional crystallization and then decomposing
the separate fractions by means of strong hydrochloric acid under
pressure at 150°. !t was found that while the piperidine obtained
from the first fraction had a much lower oxidation velocity than
the original piperidine it was nevertheless not as pure as when
purified by the first method described above.
The nitrosopiperidine was made by treating a strong solution of
piperidine in presence of excess of sulphuric acid with a saturated
solution of sodium nitrite and extracting the nitroso compound
(most of which separates out as an oily liquid) with ether. The
ethereal solution was dried with potassium carbonate, the ether'
distilled off and the nitrosamine distilled in vacuum.
' The oxidation of the impurities in this nitrosopiperidine was
carried out by adding potassium permanganate to a solution of the
nitroso compound in acetone till the color did not disappear after
six hours' standing. In the cold the reaction requires about two
days, in the heat the reaction is finished in about three hours. After
filtering off the manganese dioxide the unchanged nitroso piperidine
was obtained from the filtrate by evaporating the acetone, taking
up the residue with ether, and, after removal of the ether, distilling
the nitrosamine in vacuum.
PllA KMA CEITICA I. K KYI K IV. 39
The amount of potassium permanganate consumed in this reac

tion is much greater when t he liquids are allowed to get hot during
the reaction than when they are kept down by cooling to ordinary
temperature. As the properties and even the yield of pure piperidine
are the same in both cases the difference in the amounts of potassium
permanganate consumed, must be explained by assuming that at a
higher temperature either the impurities undergo a further oxidation
or the acetone itself is oxidized.
The elimination of the NO group from the nitroso piperidine
could not be conveniently effected by means of sulphur dioxide in
hydrochloric acid solution. It was carried out by passing hydro
chloric acid gas into a solution of a nitroso compound in toluol till
the evolution of nitrosyl chloride ceased and piperidine hydrochloride
separated out.
The pure piperidine was obtained from the piperidine hydro
chloride by distilling the salt with excess of potassium hydroxide.
(Ann. 345, 277.)
Purine.
0. Isay has devised the following synthesis of purine. 5-nitrouracyl
(I) is converted by means of phosphorous oxychloride into 2.4-di-
chlor-5-nitropyrimidine (II), the latter when treated with ammonia
in the cold is transformed into 4-amino-2-chlor-5-nitropyrimidine (III)
which upon reduction with hydriodic acid and phosphonium iodide
gives 4.5-diaminopyrimidine (IV) and the diamino compound when
condensed with formic ncid yields purine (V).
N'H CH N==CH N--CI1
| I PO.CU i I NH« | | HI
CO C.NO2 > C.Cl L'.NOs > C.C1 C.NO2 >.
I| il I I I PH4I
NH CO N C.Cl N C.NH2
(I) (III (HI)
N=-CH ,N==6CH
> CH
I C.NH2
I H.COaH > aCH I bC.t.NH.
I
N C.NHa sN *C .
(IV) (V)
Purine.
The yield of purine by this method is very small for the reason
that the preparation of the o-nitronracyl and its conversion into
2.4-dichlor-5-nitropyrimidine are connected with considerable loss of
material.
The 5-nitrouracyl was prepard from methyluracyl by the method

of Behrend and Lehmann (Ann. 240, 4; 251, 238). It was separated
from the 5-nitrouracyl-4-corboxylic acid formed in the reaction by
recrystallizing the compound from hot water.
The 2.4-dichlor-5-nitropyrimidine was prepared by heating 5-nitro-
uracyl with a large excess of phosphorus oxychloride to about 185°
in sealed tubes under constant shaking. The length of time required
to carry the reaction to a finish depends upon the amount of hydro
chloric acid present in the phosphorus oxychloride. It is, therefore
best to redistill the oxychloride so as to remove all the acid and
then add a couple of drops of the latter. The reaction product is
distilled in vacuum at 55° and the unchanged oxychloride removed
by means of ice water. The pyrimidine compound is then shaken
out with ether and, after removal of the ether, purified by distillation
in vacuum. It forms shining leaflets melting at 29.3° and boiling
at 153—155° at a pressure of 58 mm. Its vapors have a penetrat
ing odor and attack the eyes.
On treating the 2.4-dicblor-5-nitropyrimidine (II) with cold
alcoholic ammonia the 4-amino-2-chlor-5-nitropyrimidine separates
out immediately as a white precipitate and can be recrystallized
from hot water. By using standardized ammonia it could be shown
that the reaction takes place according to the following equation :
C*N2H(N02)C12+ 2NHs = NH4C1 + C.N2H(N02)CI(NH2).
As in most pyrimidine derivatives the chlorine atom in 4 is more
easily replaceable by the NH2 group than the chlorine atom in the
mesoposition the compound obtained in the last reaction must eon-
tain the NH2 group in 4, not in 2. This was also shown by the
fact that after converting the NO2 by reduction into the NH2 group
the resulting compound gave all the reactions of orthodiamines.
The 4-amino-2-chlor-5-nitropyrimidine is soluble in strong hydro
chloric or sulphuric acids and separates out unchanged upon dilution
with water. It is also soluble in alkalies but cannot be recovered
from such solution. It is not affected by boiling silver nitrate and
has a neutral reaction. It affects the eyes and the mucous membrane
of the nose and throat and causes burns on sensitive skin.
Sulphur dioxide had no effect upon 4-amiuo-2-chlor-5-nitropyri-
midine but hydriodic acid and phosphonium iodide reduced it to
4.5-diamino-pyrimidine (IV) which melts at 202.5° and boils at 229°
under a pressure of 32 mm. It is very easily soluble in water and
alcohol but insoluble in ether. It forms a hydrochloride, a hydro-

bromide, a chloroplatinate, a chloraurate and a picrate.
When the 4.5-diaminopyrimidine is boiled with anhydrous formic
acid and, after removal of excess of acid, the liquid made alkaline
with ammonia formyl-4.5-diaminopyrimidine separates out in pris
matic crystals.
N==CH
I I
CH C.NH.HCO
II II
N C.NHa
Formyl—4.5—iHamlnopyrlmidlue.
As experiments had shown that only such pyrimidiue derivatives
had an alkaline reaction as contained an NH2 group in 4 or 6
and the formyl compound had an alkaline reaction in aqueous solu
tion the compound must contain the formyl group in 5.
On heating the formyl compound first in an atmosphere of car
bon dioxide and then in vacuum it is transformed into purine ( V)
which distills over as an oily liquid and which soon solidifies to a
mass of needle-shaped crystals. The identity of this purine with the
compound obtained by E. Fischer was established by a comparison
of the melting points of the substance itself as well as of its picrate
and nitrate. Other reactions of purine described by Fischer were
also given by the synthetic compound of the author.
The 4.5.diaminopyrimidine (IV) was also condensed with other
substances as follows :
1. On heating the diamino compound with acetic anhydride in
an atmosphere of carbon dioxide to 210° and then distilling the
residue in vacuum 8-methylpurine distills over as a yellowish oil
which solidifies to needle-shaped crystals.
N==CH
I I
CH C.NH■
I I >C.CHa
N C . N*'
8-Methylparlne.
(VI)
The compound is soluble in water with a neutral reaction and melts
at 2(i5—266°. It gives all the reactions of the purine compounds.
2. On heating the 4.5-diaminopyrimidine with urea to 165°
ammonia is given off and 8-oxypurine is formed which melts at 31 2°
and is identical with the compound obtained by Fischer by reducing
8-oxy-2.6-dichlorpurine
12 i'H lin1ACEVriCAL REVIEW.
N-=CH
I I
CH C.NH
I I >co
N C.NH/
8-Oxypurine.
(VII)
3. On heating the 4.5-dianimopyrimidine with thiourea to 220°
in an atmosphere of carbon dioxide it is converted into 8-mercapto-
pyrine, which is soluble in ammonia and fixed alkalies, and when
heated emits an odor of caoutchouc
N==CH
I I
CH
I (J.NHs
I scs
N C.NH
8-Mercaptopurine.
iVIII)
4. On heating 4.5-diamidopyrimidine with benzyl to 175° an
azine of following constitution is formed
N-=CH
I I
CH (\N= -O.CflHb
:.S==U.C«Hb
Aline.
(IX)
The aziue is insoluble in water or alkalies, easily soluble in alco
hol, benzol and toluol. It melts at 170..")° and becomes electric
when rubbed up.
On heating the 2.4-dichlor-5-nitropyrimidine (I!) with alcoholic
ammonia in closed vessels to about 100° both chloriue At.wms are
replaced by NH2 groups with ±he -formation of 2.4-diamino-5-nitro-
pyrimidine
X =CH
I I
C.NH2 U.NO2
I II
N C.NH2
2.4.-dlamlni>-.tWnltropyrimldlne.
(X)
The diamino compound does not melt even at 200° and sublimes
at a high temperature with partial decomposition. It is difficultly
soluble in water and and forms salts with acids.
By reducing this diamino compound with stannous chloride it is
converted into 2.4.5-triaminopyrimidine
PHA RMACECTICAL REVIf: \V. -I-:!
N^=C
I I
C.NH2 C.NH2
I I
N C.NHa
2.4.5-triamIuopyrimIdine.
(XI)
The triamino compound melts at 170—179° and is isomeric with
the triamino compound previously obtained from barbituric add by
Gabriel (Ber. 34, 3364) which melts at 245—246°. It has a strong
alkaline reaction, reduces Fehling's solution and precipitates metallic
gold from gold chloride. It is very difficultly soluble in ether, chloro
form or petroleum ether, but easily soluble in acetone or alcohol
with a red color.' It forms difficultly soluble salts with acids and
gives the murexide reaction. Exposed to the air it becomes red.
On boiling the triamino compound with crystallized formic acid
for half an hour it is converted into formyltriaminopyrimidine
N=CH
I I.
C.NH2 C.NH.HCO
II I
N C.NHa
Formyltriaminopyrimidine.
As the formyl compound has an alkaline reaction and is capable
of forming a closed ring the formyl group must be in 5, not in 2 or
4 (see above formyl-4.5-diaminopyrimidine). The formyl compound
melts at 224°, becomes solid at a higher temperature and then does
not melt at 260°. It is difficultly soluble in water or alcohol and
forms salts with acids.
On heating the formyl compound to 300° it is converted into
2-aminopurine or isoadenine
N CH
I I
C.NHa C.NHs
II I >CH
N C.
L'-amlnopurlne (Uondenlne).
(XII)
The isoadenine differs from adenine (6-aminopurine) in not giving
a purple color with zinc and hydrochloric acid (Ivossel and Fischer's
reaction) and is identical with the isoadenine previously obtained
by Tafel and Ach (Ber. 34, 1177). (Ber. 1906, 250.)
Northwestern University,
School of Pharmacy.
( To he continued. I
Plant Pigments.'
By /. W. Brandel.
i>
^'Nj■—CHt—< 'H=CH— / ^.
\
Diphenyl-l-2-propene-2. Flavone.
CH2 = CH- /X
CHs C2H5
Methyl-2-fthyl-2'-dlphenyl-l-2, ethylene.
C'H2 O
I CH2- - 0
n : I
o
\
OCHs CH I 'i
OCHs C
CHgO// \/ \"7 /\ / \ / • /
rir.to / " '
. /\ *\ /CH2 ! I I'
\/ \/N \/ CH2
CH | C 1 1 2 V V. N\/'
OH CH CH2
lierberlne hydroxide. Berberine.
The rather large number of dyestuffs belonging to the flavone
group, although oecuring in a great variety of plants, bear a very
simple relation to each other. The first member, chrysin, is a
dihydroxyflavone ; galangine and apigenine are both trihydroxy
derivatives of flavone, viz. ?, 1, 3, and 1, 3 4' respectively.
Acacetine is a methylether of apigenine, the methoxy group
being in position 4'. Fisetine, luteoline and kaempherol are tetra-
* Continued from Vol. 25. pnge 878.
hydroxy derivatives of flavone. Kaempherid is a methyl ether of

kaempherol. There are two pentahydroxyflavones, viz. quercetin and
morin. Rhamnetin and isorhamnetin are methyl ethers of quer
cetin and rhamnazin is a dimethyl ether of quercetin. Myricetin is
one of the theoretically possible hexahydroxyflavones.
These substances are all yellow crystalline compounds, and are
important not only as plant pigments but also as dyestuffs. Their
sodium, potassium and lead derivatives are yellow and with salts
of iron they give red or green solutions. They have been isolated
from a great variety of plants in which they all occur potentially
as glucosides with the exception of chrysine, galangine, luteoline
and kaempherid. These four are found in the plant as such. Quer
cetin is found both in a free condition and as glucoside in a greater
number of plants than any other dyestuff of the flavone group. It
is obtained upon the hydrolysis of the glucosides quercitrin, robinin,
rutin, myrticolorin and osyritrin.
It is interesting to note that whereas acacetin, an apigenine-
monomethyl ether, is found as a glucoside in the leaves of Robinia
pseudacacia, a quercetin (a dihydroxyapigenin) glucoside is found in
the flowers. We have, therefore, again the occurrence in the flower
of a leaf constituent in a more oxidized condition.
The leaf buds of different species of poplar contain chrysin, while
the full grown leaves do not. Many of the compounds of the flavone
group occur in the flowers of different plants. Quercetin as a
glucoside, which is almost white, is found in the white blossoms of
Crataegus oxyacantha*2 while in the yellow flowers of Cheiranthus
cheiri** the yellow quercetin as well as its colorless glucoside are
found. The reddish-yellow flowers of Aesculus hippocastanum**
contain both the glucoside quercitrin and the yellow dyestuff quercetin
in considerable quantity. The leaves and twigs, however, of this
same plant contain only mere traces of either quercitrin or quer
cetin. The yellow flowers of Delphinium zalili5 contain quercetin
and isorhamnetin both free and as glucoside.
Robinin, the colorless glucoside of the yellow substance kaem-
pherol is found in the white flowers of Robinia pseudacacia *e. The
free kaempherol does not seem to occur in these flowers. These and
« Journ. Chem. Soc., 69, p. 1570.
Journ. Chem. Soc., <H>, p. 157 0.
** Journ. f. p. Chem., 77, p. 34.
*s Journ. Chem. Soc.. 73, p. '2t>7.
*• Journ. Chem. SSoc. 81,, p. 478.
.if. PHA RMACEUT1CA L REVIEW.
other cases which might be mentioned would indicate the possibility

of quercetin either as such or as its potassium or sodium derivative,
which are more intensely yellow, and of other fiavone derivatives
producing the yellow color in some flowers. In fact the wide occur
rence and behavior of quercetin has been made the basis of an un
tenable hypothesis of plant pigmentation. (By Hlasiwetz.) That
these dyestuffs, or their yellow metallic derivatives, are not always
the pigments to which the flower owes its color primarily is shown
by the occurrence in considerable quantity of the glucoside robinin
and its product of hydrolysis, the yellow kaempherol in the blue
flowers of Delphinium consolida.*"
In general the compounds of this group are much stronger dye-
stuffs than those of the xanthone group. This is to be expected
from the fact that most of the compounds contain a greater number
of hydroxy groups thus rendering more eusy the formation of the
metallic derivatives of the trivalent metals used as mordants. Not
one of these compounds contains two hydroxy groups in positions
1 and 2, a condition which Lieberman and Kostanecki gave as
essential in the case of the anthraquinone dyestuffs.
Comparing the strength of the dyeing properties of these com
pounds again from the point of view of the comparative tendency
to form metallic derivatives with aluminium, iron or chromium, it
is seen that those compounds are the strongest dyestuffs which have
two or more OH groups connected to neighboring carbon atoms.
Thus quercetin
0
OH C
' \/\0H
H0\/\/ OH
o
and rhamnetin
()
OH C
/\/\0H
" Journ. Chem. Soc.. 81, p. 585.

/'//. 1 KMACEUTICA L REVIEW. IT
which is a methyl ether of quercetin, both have two hydroxy groups

connected with neighboring carbon atoms and both have approxi
mately the same dyeing property. Isorhamnetin
o
I
OH C
OH
Ho\ '_)°a
0 OU Ha
however, which is also a methyl ether of quercetin, on account of
the position of the OCH3 group, no longer has two hydroxy groups
connected with neighboring carbon atoms and accordingly dyes with
less intensity. That the dyeing property in general can be decreased
by converting a hydroxy OH group to a methoxy OL'Hs group is
again shown by the fact that whereas apigenine, a trihydroxy deri
vative, dyes a bright yellow, acacetine, a monomethyl ether of api-
geniint, dyes a very faint yellow about equal in intensity to the
dihydroxy derivative chrysine. Again kaempherid, a monomethyl
ether of kaempherol, dyes a lighter color than kaempherol.
Besides the flavone group of compounds, there still remain under
the degree of saturation CuIIan— ie several substances having a
different constitution, yet referable to hydrocarbons which are
homologues of the hydrocarbon underlying flavone.
Gossypetine, a yellow crystalline substance, is found in the yellow
flowers of Gossypium herbaceum in the form of a glucoside. Whether
the color of the flowers is due to the presence of some free gossype
tine has not been determined. Its potassium derivative is yellow,
its lead compound red, and it gives green solutions with iron salts.
It is remarkable that indigo, a substance of an entirely different
nature, can be referred to the same hydrocarbon as gossypetine.
Indigo is found as the glucoside indican in Indigofera tinctoria,
Polygonum tinctoria, Isatis tinctoria and other plants.
Scutellarem is a yellow crystalline substance obtained by heating
scutellarfn, occuring in many Scutellaria species, with potassium
hydrate. Its metallic derivatives are very similar to those of gossy
petine. Like the compounds of the flavone group, scutellarefn and
gossypetine still contain a carbonyl group and a cyclic oxide oxygen.
Indigo also contains carbonyl groups but in place of the oxide
oxygen, it contains nitrogen, still lea ving the compound heterocyclic.
4S PHARMACEUTICAL REVIEW.
Braziline obtained from Brazil wood and haematoxyline obtained

from the wood of Haematoxylum campechianum, do not contain a
carbonyl group. When crystallized from alcohol braziline and haema-
toxyline are colorless crystalline substances, which rapidly become
red undergoing oxidation. From the solutions of these two sub
stances in caustic alkali, which rapidly become brown in contact
with the air, brazilem and haematem are obtained. Brazilem and
haematem are red crystalline substances which are products of oxid
ation of braziline and haematoxyline. These two compounds again
contain a carbonyl group. They as well as their products of oxid
ation, brazilem and haematein form colored metallic derivatives
which are violet-red and sometimes even blue. The esters and ethers
of the colorless braziline and haematoxyline are also colorless while
the esters and ethers of the red brazilem and haematem are yellow.
Although the woods from which these dyestuffs are obtained com
mercially contain only braziline and haematoxyline from the ease
with which these substances can be oxidized to the more highly
colored brazilem and haematem, one might readily suspect the
presence of these latter compounds acting as plant pigments in other
parts of the plant.
Berberine, one of the few colored alkaloids and the only alkaloid
used as a commercial dyestuff, is a yellowish-brown crystalline sub
stance found in a large number of plants. Its relation to the other
dyestuffs, in being able to refer it to a similar hydrocarbon, has
already been spoken of.
Eilagic acid is the only dyestuff under this degree of saturation
which must be referred to an entirely different hydrocarbon from
the rest of the compounds, viz. diphenylenemethane. This can be
prepared from ellagic acid. Ellagic acid is a yellow crystalline sub
stance ocurring very widely in nature as ellagitannic acid. Its com
pounds with the metals are yellow. A solution of ellagic acid is
turned green and then blue-black by the addition of ferric chloride.
C1tH2—nIs to C1tH211—3o.
The compounds under the remaining degrees of saturation are
only few in number and have been studied but little. They will be
considered, together here.
Two quinones are known belonging to the degree of saturation
CnHan-is, viz. fluoranthenequinone and /J-phenyhiapbtoquinone.
PHA RMA CE I TICA L REVIEW. 4ti
They are obtained by the oxidation of the hydrocarbons fluoranthene

and /3-phenylnaphtalene to which they have been referred. They are
crystalline substances, fluoranthenequinone being red and /8-phenyl-
naphtoquinone, yellow. Upon reduction both yield colorless hydro-
quinones. Phenvlnaphtylquinhydrone, a blue crystalline substance
is obtained upon the incomplete reduction of /} phenylnaphtoquinone.
The hydroxyphenylnaphtoquinone, the colorless hydroxyphenyl-
naphtohydroquinone and the blue hydroxyphenylnaphtoquinhydrone
have also been prepared. The metallic derivatives of the hydroxy-
phenylnaphtoquinone are brown.
Pyrenequinone " belonging to the degree of saturation CnH2n-2o
is obtained in the form of red crystals, by the oxidation of the
tetracyclic hydrocarbon pyrene. It is curious to note that the two
('=0 groups are in different, widely separated cycles.
o
c
'I
0
Its corresponding hydropyrenequinone is described as having a
yellow color. Inasmuch as this is the only hydroquinone which is
colorless, the purity of the substance described may be questioned.
The only other quinone belonging to this degree of saturation
is 1, 3, diphenylbenzoquinone, which is a red crystalline substance.
No hydroxy derivatives of these compounds are known.
Four quinones are known belonging to the degree of saturation
CnHan—22. Chrysoquinone is obtained as orange-red crystals by the
oxidation of the hydrocarbon chrysene to which it has been referred.
Naphtanthraquinone, is a yellow crystalline substance which has been
referred to the known hydrocarbon naphtanthracene. There are two
known quinones referrable to the hydrocarbon naphtacene, viz.
naphtacenequinone and naphtacenediquinone. The latter is obtained
by the oxidation of the dihydroxy derivative of naphtacenequinone.
Only one' hydroquinone corresponding to these quinones is known
viz. hydrochrysoquinone. The quinhydrons have not been prepared.
Under the degree of saturation CnQan—a«, 2-naphtyl-naphtoqui-

none, 1, 4, and di-2-naphtodiquinone can be referred to the same
hydrocarbon dinaphtyl from which they also can be prepared by
direct oxidation. Hydroquinones or quinhydrones of these com
pounds are unknown. A monohydroxy derivative of 2-naphtylnaph-
toquinone and a dihydroxy derivative of di-2-naphtodiquinone can
readily be prepared, by the oxidation of the corresponding quinone
with dilute caustic alkali.
By heating 1, 2, /J-naphtoquinone belonging to the degree of
saturation CnH2n—io, with sulphuric acid, a binaphtyldiquinhydrone
belonging to this degree of saturation is obtained. This is a blue-
black powder which upon oxidation yields a yellow dinnphtyldiqui-
none and upon reduction a colorless dinophtyldihydroquinone.
There are known, furthermore, under this same degree of satura
tion, the hydroxy derivatives of two quinones which are unknown.
These compounds are culled ethylidene-/J-dihydroxy-a-naphtoquiuone
and isoamylidene-a-dihydroxy-naphtoquiuone. They are yellow sub
stances, the former of which is obtained by the condensation of
2-hydroxy-a-naphtoquinone with ethaldehyde and the latter by the
condensation of 2-hydroxy-a-naphtoquinone with isovaleric aldehyde.
Corresponding reduction products have not been obtained.
Under the degree of saturation CnH2n-26, two quinones are
known. The first called 2-benzhydrylnaphtoquinone, 1, 4, is a
diphenyhnethyl derivative of naphtoquinone, 1, 4, and the other is
a diphenylmethyl derivative of ortho naphtoquinone. The former is
a yellow substance which yields a yellowish-red dihydroxyderivative.
Picenequinone and crackenequinone both of which ore red sub
stances, belonging to the degree of saturation CnH 2n-28 are obtained
by the oxidation of the hydrocarbons picene and crackene. Crackene
quinone yields a reduction product which has undoubtedly not been
obtained in a pure form, judging from the color which is ascribed to it.
There are n0 quinones known having the degree of saturation
CnH2n—32, but the dihydroxy derivative of benzylidenedinaphtoqui-
none has been prepared. This a yellow compound, the disodium
derivative of which is a dark carmine red powder.
The degree of saturation CnH2n-3o contains the 1, 4, bis-benz-
hydrylquinone, 2, 5, which can be regarded as benzoquinone in which
two hydrogen atoms in para position are substituted by two
diphenylmethyl radicles. This is a yellow compound which upon
reduction yields the corresponding well characterized hydroquinone.
{To be continued.)
Percolation.*
By /. W. Branilel and Ed. Kremers.

Brown, A. E. 1897.
Rapid preparation of tincture of iodine.
Proc. Alabama Ph. A., 1897, p. 15. [Proc. A. Ph. A., 46, p. 745.]
The author recommends percolation.
Kelly, D. C. 1897.
Comparative experiments on repercolation.
Proc. Kansas Ph. A., 1897, p. 40. [Proc. A. Ph. A., 46, p. 683.]
From the use of the ordinary process of repercolation in the preparation
of 50 p. c. tinctures of gentian, uva ursi and squill, the conclusion is drawn
that repercolation does not completely exhaust the drug.
Musset, F. 1897.
Preparation of fluidextracts by repercola
tion.
Pharm. Centralh., 1897, p. 862. [Proc.
A. Ph. A„ 46, p. 681.]
Recommends repercolation for all fluidextracts,
with the apparatus as shown in illustration.
V Opposes the use of fine powders, preferring the
No. 3 powder of the Pharm. Germ, (passing
P7J through two m. m. meshes). Process consists of
macerating drug in a covered vessel ; place
menstruum in the percolator; pour in the drug
and stir to form a thick magma. Percolate
without packing.
Fig. 35. Repercolator for
fluidextracts.
Norris, G. B. 1897.
• Influence of temperature on percolation.
Proc. Kansas Ph. A., 1897, p. 41. [Proc. A. Ph. A., 46, p. 684.]
Experiments on the preparation of 50 p. c. tinctures of belladonua, gel-
semium, valerian,- sarsaparilla and senna by the U. S. P. process of perco
lation, at 0° C., 20° C , and 38° C., show that the extraction is moro com
plete at higher temperatures.
* Continued from Vol. 25, page 348.
Sayre, L. E. 1897.
A problem of drug extraction by percolation.
Drugg. Circ., 1897, p. 212. [Proc. A. Ph. A., 46, p. 685.]
A continuation of a previous article. Repercolation is insufficient to
totally exhaust drugs in making 50 p. c. tinctures.
Benyschek, H. 1898.
Preparation of infusions by percolation.
Pharm. Post., 1898, p. 759. [Proc. A. Ph. A., 47, p. 437.]
Recommends maceration followed by percolation in preparing infusions.
Experiments on infusions of ippcac, digitalis, senega and ergot.
s v Catford, J. Y. 1898.
f - A Automatic repercolation.
X^^^Jss. Chem. and Drugg., Aug. 1898, p.
271. [Proc. A. Ph. A., 47, p. 386.]
An apparatus to simplify repercolation.
It consists of 4 glass tube percolators con
nected end to end by means of corks cut
as shown at B. The receivers consist of
several small bottles, adjusted to hold a
definite quantity corresponding to the
reserve portion of the percolate. These
bottles are connected as shown at A.
C is a feeding bottle regulator.
Cowley, R. C. 1898.
Percolation under pressure.
Pharm. Journ., Oct. 1898, p. 418.
[Proc. A. Ph. A., 47, p. 385.]
Fig. 36. Automatic Repercolator.

Does not advocate the use of pressure in percolation
but for exhausting certain mucilaginous or finely
■powdered drugs recommends apparatus as shown in
illustration.
Fig:. 37. Percolation under pressure.
Kemp, D. S. 1898.
Water bath percolator.
Chem. and Drugg., 1898, p. 981. [Proc. A. Ph. A., 47, p. 389.]
An apparatus for percolation requiring a hot menstruum.
Nnnn, A. W. 1898.
Percolation under pressure.
Pharm. Journ., Oct. 1898, p. 371. [Proc. A. Ph. A., 47, p. 384.]
Pressure is produced by means of an ordinary bicycle pump.
Weber, Wm. 1898.
Superiority of maceration over percolation for making tinctures.
More certain and uniform products are obtained.
Wolff, D. J. 1898.
Moistening of powders.
Am. Drugg., 1898, p. 36. [Proc. A. Ph. A., 47, p. 382.]
Directions for a convenient method of moistening powders preliminary
to percolation, together with advantages.
Bernard, J. E. 1899.
Improved percolator.
Merck's Report, 1899, p. 220. [Proc. A. Ph. A., 47, p. 387.]
A, percolator.
It and H, right angled, threaded flanges*
C, tight fitting, threaded cover.
E. receiver forming tight joint at H.
P, a tube, W, a porous or perforated
septum.
Fig. 38. Percolator, improved foi

Cohen, A. I. 1899.
Pressure percolator.
Merck's Rep., 1899, p. 4. [Proc. A. Ph. A., 47, p. 383.]
A
Fig. 39. Pressure percolator.
A pressure percolator whose construction is simple, easy and inex
pensive.
a is the percolator, a well tinned can.
r. two oblong holes, cut at opposite sides.
b, a block of hard wood with hole c at center.
0, a spout of a small tin funnel.
r/, a diaphragm of hard wood with a hole
g at center in which a rubber stopper
h is fitted.
f, u series of furrows to conduct liquid to center.
1, a short glass tube with end thickened at k.
I, a rubber tube to conduct liquid to
m, the graduated receiver.
n, n, blocks of wood to support diaphragm.
Pressure is produced by connecting o with an elevated reservoir con
taining the menstruum.
Edel, F. 1899.
Maceration vs. percolation.
West Drugg., 1899, p. 57. [Proc. A. Ph. A., 47, p. 381.]
A reply to Weber's article. See 1898.
Wood, J. R. 1899.
Syphon percolator.
Pharm. Era., 1899, p. 359. [Proc. A. Ph. A., 48. p. 399.]
A device to avoid the inconvenience of

raising and lowering the syphon-tube and
receiver in regulating the flow of Hyphon per
colators. It consists of two corks, held to
gether by a pin as shown in illustration. The
function of the top piece is to prevent the
tincture from flowing out in a jet, and cause
it to fall back into the receiver in drops.
Fig. 40. Syphon percolator.

Eberle, E. G. 1900.
Expeditious mode of moistening the powdered drug.
Place powder in an ordinary covered can, add menstruum, stir
thoroughly, put in a few glass stoppers, and shake thoroughly. Advant
ages are, thorough moistening; no loss by evaporation ; glass stoppers
prevent lumping of powder.
Jacobin, J. 1901.
Use of shredded wood to prevent clogging. ■
Pharm. Post,, 1901, p. . [Proc. A. Ph. A., 50, p. 684.]
Alternate layers of "excelsior" and drug is recommended to prevent
clogging when percolating drugs of an adhesive nature like opium, etc.
(To be continued.)
The Volatile Oils: 1901 to 1903*
By /. W. liramlel
. Cathelineau and Haussera4* recommend the following method for

producing cadinene hydrochloride:
The non-phenol part of oil of cade is distilled with steam after adding
a 40 p. c. solution of soda. The oil thus obtained is emulsified with 3
parts of 90 p. c. alcohol and the cooled mixture is saturated with dry
hydrochloric acid gas. After standing for 24 hours, the alcohol is decanted
from the lower layer, which is a pasty mass of cadinene hydrochloride. The
crystalline mass is allowed to drain on cottou, and then washed with
alcohol containing hydrochloric acid.
41. Oil of Savin. G.-H.-K., p. 272.

Fromm40 has examined oil of savin after saponification with
caustic potash and distilling the product with steam. In the residue
acetic acid and small quantities of an acid C1sHa40(COOH)2 b. p.
255° and of another acid C1iH1sO»(COOH)3 m. p. 181° were identi
fied. The oil which distilled over with steam contained 25 p. c. of a
terpene b. p. 158 and sabinol.
In the first runnings of the oil of savin, S. & Co. 41 detected
diacetyl and in a fraction of the saponified oil boiling 220—250° a
compound, either a ketone or aldehyde was separated by means of
its addition product with sodium bisulphite. The regenerated com
pound boiled at 127—129° (20 m. m.); sp. gr. 0.9163 at 16°; «„ =
+ 11° 40'. It forms a crystalline phenylhydrazone, m. p. 40—45°
and an oxime m. p. 85°.
The decomposition products of the a-tauacetogendicai borne
acid obtained upon oxidizing sabinol and the ease with which
sabinol is converted into cymene when heated with 10 p. c. alcoholic
• Continued from Vol. 2."', page 366.
»»
*o Bull.
Ber.. Soc.
33, p.Chim , III, 25, p. 931.
1191.
*' S. & Co., Rep., Oct., 1900, p. 62; April, 1900, p. 43.
hydrochloric acid, led Fromm42 to offer the following formula for

sabinol :
CH2
HaC\
CHs CHs
From the same experimental results Semmler43 has devised the
formula which differs from the former
CH2
II
C
H2C/ \CHOH
l\ I
\
H«C\\ /CH2
V
L
CHs CHa
in the position of the diagonal linkage.
Semmler4a has termed the terpene from savin oil, sabinene and
determined the following constants: Sp. gr. 0.84; n„ = 1.406. It
yields an oily dibromide. Sabinene has the formula:
CH2
II
('
l\ /CH«
HsC\\ 1
X/
(;
CH
/\
( Hs CH3
" Ber., 88, p. 1191.
« Ber., «8. p. 1455.
Terpene derivatives which contaiu a double bond between the

nucleus and the sidechain are called pseudo-terpenes by Semmler, the
isomeric substances being called ortho-terpenes. Thus limonene)
CHs
I
('
/
H2C/ CH
I I
I I
H2L'\ /CH2
\y
CH
i
C
CHr CH
is an ortho-terpene, the corresponding pseudo-compound having the
formula :
CH2
II
i;
HtC/ \CH2
I I
I I
H2C\ /CH2
CH
A
/\
CH3 CH
•
It is not improbable that dipentene has the latter formula instead
of being (d + 1) limonene. Sabinene is a pseudo-terpene. Oil of savin
is official in the Belgian Pharmacopoeia with the following require
ments: Colorless or yellowish, sp. gr. at 15° = 0.910—0.930 soluble
in one-half volume of alcohol.
44a. Atlas Cedar Oil.
Atlas Cedar oil is distilled from the wood of Cedras atlamica,
Manetti, a variety of Cedrus libani, Barr. The oil is a thick, pale-
yellow liquid, with a balsamic odor. Sp. gr. 0 9517; «„2o=+48°
1"'; nt>ao — 1.51487. Soluble in 3 to 4 parts of 90 p. c. alcohol,
which becomes cloudy upon further addition of alcohol. It has a
saponification number 40.6 corresponding to 16.0 p. c. of an alcohol
C1SH260.4*
« 8. & Co., Rep., April, 1901, p. 5«.
According to Grimal*5 the oil has a sp. gr. at 15° = 0.9508;

aD = +60° 32'; nD = 1.51191; soluble in 8.5 parts of 90 p. c. alcohol ;
acid number 1.16; saponification number 6.92; acetylation number
33.84. The oil contains a ketone C9H14O (semi carbazone, m. p.
159—160°) to which the peculiar odor of the oil is due. D-cadinene
(hydrochloride m. p. 117—118°) is the principal constituent. The
cadinene regenerated, had sp. gr. 0.9212; b. p. 274—275°; nDau° =
1.5094; [a]O20o= +47° 55'. A pure dextrogyrate cadinene had not
hitherto been known. The oil also contains traces of acetone and
one or more sesquiterpene alcohols.
Boisse*5 found the oil to contain about 16 p. c. of a sesquiter
pene alcohol. Ordinary cedar wood oil contains only 2 p. c. The
efficiency of sandalwood oil depends upon the presence of a large
percent of such alcohols.
44b. Oil from Dammar Orlentalis.
Tschirch and Koch4" obtained 6 p. c. of a colorless oil with a
pleasant odor from Manila copal derived from Pnmimira orientalis.
Sp. gr. at 15° = 0.840; b. p. 165—170°.
44 c. Oil from Cryptomeria Japonica.
Kimoto*7 obtained an oil by distilling with steam the wood of
Cryptomeria juponica. The wood has a peppermint-like odor and is
used to make goblets. The fraction of oil containing the odoriferous
compound boils at 260—270° and contains a camphor-like body
called sugiol which is probably a sesquiterpene alcohol, b. p. 264°;
sp. gr. 0.935.
OILS OF THE GRAMINE^.
46. Palmarosa I East Indian Geranium) Oil. G.-H.-K.,p. 281.
S. & Co. is have tested a number of commercial samples of
palmarosa oils with the following results: \
Sp. «r. «i> at Sap. no. P. e.
at 15°. after
16—2o°. aeetylation. of alcohol Solubility in TO p. c. alcohol.
C'ioHIHO.
A. 0.8964 + 3° 12' 259.0 88.40 Insoluble in 10 parts.
B. 0.8967 + 0^ 42' 246.93 83.34 2—3 parts.
0. 0.9024 + 3° 50' 234.6 78.29 2—3 parts.
I). 0.8931 — 3° 11' 190.8 61.23 2 parts, becoming cloudy.
E. 0.9010 — 0° 4' 222.89 73.60 2 parts.
F. 0.9i'O2 + 7° 40' 210.5 68.74 Insoluble.
G. 0.8926 + 6° 7' 234.8 78.37 Insoluble.
H. 0.893i ) + 0° 33' 256.75 87.45 2 parts.
I. 0.8923 -1° 8' 247.9 83.70 2 parts.
*s Chem. and Dru^g.. (!1, p. 286.
*« Arch. d. ►'harm.. 240, p. 202.
" Bull. Coll. Agrlc.. Toklo. 4. p. 403.
«» S. & Co., Kep.. April, 1901, p. 87.
(iO PHARMACEUTICAL REVIEW.
Samples C, E and F have an abnormally high sp. gr. ; A, C, D,

F and G have an exceptionally high rotatory power, pointing to
the presence of ginger grass oil. A, F and G should be rejected be
cause of the insolubility in 70 p. c. alcohol. D and E have too low
an alcohol content. B. H and I are the only oils which can be called
normal.
48. Lemon-grass. G.-H.-K., p. 285.
S. & Co. 49 have examined a Jamaica oil designated as having
been obtained from Andropogon schoenauthus, but it had such a
pronounced odor of lemon-grass oil that it was undoubtedly such.
Sp.gr. at 15° = 0.8922: «„=-0°9'; nD at 20° = 1.48825; insoluble
in 70 and 80 p. c. alcohol; contains 83.5 of aldehyde. Parry no ob
tained similar results with an oil likewise designated as oil from
Andropogon schoenauthus. It. differed from normal lemon grass oil
from Andropogon citratus, only in its insolubility in 70 or 80 p. c.
alcohol.
Mannich31 has determined that the oil from an Andropogon
species from Cameroons, is true lemongniss oil and not an oil
distilled from Andropogon nardus as reported by Strunk."2
The oil had a sp. gr. 0.885; turbid solution in 80 p. c. alcohol;
contains 70 p. c. of citral, but no citronellal or geraniol.
It is very evident that the Andropogon grasses are frequently
mistaken one for the other and the commercial are consequently of
a varying character.
A sample of lemongruss oil from the Government Laboratory at
Antiqua, W. I., had sp. gr. at 15° = 0.8956; = —0°11'; aldehyde
content 76.5 p. c. ; insoluble even in absolute alcohol. Here, ngain,
the oil can not compete with the East-Indian oil on account of its
insolubility. The question arises whether the difference is due to
climatic conditions or to the manner of distillation/'3
According to Cousinss4 fresh grass of Andropogon citratus, D. C.,
yields 1 c. c. of oil per pound; dao° p. = 0.8897: «„ = —1°0' in 20
m. m. tube.
Parry5s has found acetone used as an adulterant of lemongrass
oil.
*» S. & Co., Kep , April. 1908, p. 49.
•o Chem. & Dru(wt.. 68, p. .107.
»> Rer. d. D. Pharm. Gea.. 1a, p. 86.
«a Trnpenpflnuzen, 7, p. 87.
"a S. & Co.. Ilep.. April 1002, p. 48.
« Jam. Bull. Dept. A«rlc , 1it03, p. 49; S, & Co., Kep., Oct., 1908, p. 27.
»» Chem. & Drufjg.. 0L'. p. 768.
PH. 1 IMA CE VT1CA L REVIEW. (il
Ziegler58 prepares artifical violet, having on odor like the con

stituent from Iris florentina oil, as follows :
Lemongrass oil is dissolved in acetone, and alcohol and cobalt nitrate
added. After warming to 50° C, filtered bleaching powder solution is added
and the mixture boiled for several days. When the reaction is ended, the
solution is very slightly ucid. The product is boiled for a week with sodium
acid sulphite solution with continual stirring, the apparatus being so
arranged that volatile substances of bad odor can distill over and be re
jected. The oil is then fractionated in a current of steam, 3 times, the
lower tractions being rejected. The fraction boiling 140—150°; d — 0.946
to 0.963 is retained.
49. Oil of Vetiver. G.-H.-K., p, 289.
Theulier57 has examined oil of vetiver, distilled at Grasse and
on oil obtained from Reunion. The former was more viscid and had
a stronger aroma. The oils had the following quite different pro
perties :
QraBse oil. Reunion oil.
Sp. gr. at 20° 1.0091 0.986
aD at 20° +35° 10' +28°
Saponification number 44.40 18.28
Acid number 32.48 6.16
Ester number 11.92 12.12
Solution in 80 p. c. alcohol 11.5 1:1.5
These differences may be due to the use of dried roots for distil
lation at Grasse and fresh roots at Reunion.
Composition. Genvresse and Langlois58 have examined an
oil from Bourbon and another from Grasse. The neutral Bourbon
oil had a sp. gr. 0.993; = +23° 43' in alcoholic solution. The
Grasse oil had an acid reaction, sp. gr. 1.012; «u = +27° 9'. Upon
steam distillation of the oil, a fraction lighter than water and one
heavier than water was obtained. The former consists of a sesqui
terpene vetivene, b. p. 262—263° (740 m. m.); sp. gr. at 20°=0.932;
aD = 4-18° 19', and the heavier fraction of a sesquiterpene alcohol,
vetivenol, b. p. 169—170° (15 m. m.); sp. gr. at 90° = 1.011; a„ =
+53° 43' (in alcoholic solution). The odor of the oil is due to an
ester of this alcohol.
S. & Co.50 have detected methyl alcohol, furfurol and diacetyl
in the distillation water of vetiver oil.
«« Ztschr. f. angew. Chem., 1900, p. 404.
« Bull Soc. chTm., Ill, L'5, p. 454.
«« Compt. rend.. 185, p. 1059.
»» S. & Co . Rep., April 1900. p. 45.
(12 PHARMACEUTICAL REVIEW.
50. Citronella Oil. G.-H.-K., p. 291.

Properties. By the distillation of the fresh grass of Andropo
gon nardus, Cousins60 obtained 2.9 c. c. of oil per pound of grass.
Sp. gr. at 60c F. = 0.8935; «„ = +17°0'.
Three samples of oil from unknown Andropogon species, but
presumably citronella oils hail the following constants:
dia° «i> ni)20c CI0H,„O
0.8889 +13° 26' 1.46466 49.09 p. c.
0.8014 +10° 6' 1.46684 50.90 p. c.
0.8809 J- 13° 52' 1.46496 49.18 p. c.
A sample of Jamaica oil from Andropogon nurdus according to
Parry01 had a pale color and an exceptionally pleasant odor. Sp.
gr. at 15° = 0.8955; «„ = —3° 30'; nD = 1.4712 at 20°. It con
tained 25 p. c. of aldehydes and 87 p. c. of geraniol and citronellal.
Soluble in 1 volume of 80 p. c. alcohol, the solution acquiring a
faint opalescence upon dilution with 10 volumes of alcohol.
According to S. & Co. 62 a citronella oil, called Malta pangiri has
been introduced from Java which is of a decidedly finer quality
than the previously known Lana Tiatu oil."3 A comparison is given
in the following table: <
Solubility Methyl-
dl5° ai>ao° In 80 p. v. ale. Citronellal. Geraniol. eutfenol.
Maha pangiri.. .0.892 —0°50' 1:1+ 50.45 p. c. 38.15 p. c. 0.78 p. c.
" ...0.892 —2°26' 1:1+ 55.34 p. c. 31.87 p. c. 0.84 p. c.
Lana Butu 0.908 —9°35' 1:1 28.2 p. c. 32.90 p. c. 8.00 p. c.
The Maha pangiri is distinguished by its high citronellal content
and low methyl eugenol content.
Composition. S. & Co.92 have isolated d-citronellol from Java
citronella oil. The pure citronellol had di5° = 0.866; aD = 4-l°45°'.
The silver salt of the acid phthaliu ester melted at 125—126°.
From the last of the three samples of oil from unknown Andro
pogon species, spoken of above, S. & Co.04 have isolated 1-citronellal.
B. p. 205-208°; d15° = 0.8567; nD20° = 1.44791 ; «„ = -3°. M. p.
of semicarbazone 74°. Cineol was also detected.
By treating camphene with a solution of mercuric acetate, Bal-
biano & Paolini05 obtained a solid mercury compound of camphene
•o Bull. Dept. Agr. Jamaica, 1, p. 49.
«i Chem. & Vrugg.. 68, p. 507.
« S. & Co., Kep., April, 1900, p. 12.
«» G.-H.-K.,
& Co., p. 295.April, 1902, p. 20.
•* 8. Kep.,
« Ber. 85, p. 2995.
rHMi.UA VEUTWAL REVIEW. <!3
S. & Co. 60 have made this reaction available for the detection of
camphene in oils as follows:
The fraction of the oil boiling between 158°—162° is dissolved in an
equal volume of benzene and the solution treated with a solution of mer
curic acetate at ordinary temperature. The separated compound is washed
with water, alcohol and ether until white. The compound is suspended in
water and hydrogen sulphide passed in for 4—5 hours with frequent shak
ing. The black compound is filtered off and distilled with steam when the
solid camphene passes over. M. p. 49°—50°.
Camphene was identified in citronella oil by this method.
From the products obtained in the oxidation of citronellal, '
Harries and Schauwecker67 have derived the following formula for
citronellul :
CHs.CCH2CH2.CH2CH.CH2CHO
II I
CH2 CHa
It is therefore methylene-2-methyl-(5-octmie-al-8.
Adulteration. The extensive adulteration of citronella oil has
led to a large number of communications. According to Hayley &
Co. 9S Russian kerosene oil is used because it can be easily and
cheaply obtained by the natives. Parry and Bennett08 are inclined
to believe that resin spirit is commonly used as adulterant. Oils
are considered pure that will pass what is known as "Schimmel's
test."
1 volume of the oil to be tested should make a clear solution with 1—2
volumes of 80 p. c. ulcohol at 20° C. After the further addition of 10 vol.
of alcohol, the solution should show, at most, a faint opalescence and even
after standing for 12 hours no drops of oil should separate.
In addition to this test Parry and Bennett69 recommend:
The first 10 p. c. of the oil distilled under reduced pressure, 20—40
m. m., must have a sp. gr. not below 0.858 and a nn not below 1.4570 at
20°. Sp. gr. of original oil at 15.5° -0.900—0.915; «n = 0° to —15°; total
geraniol (geraniol and citronellal) above 58 p. c.
OILS OF ARACEÊ.
54. Calamus Oil. G.-H.-K., p. 301.
Composition. Thoms and Beckstroem70 have examined cala
mus oil having d2o°= 1.0254; aD in 200 m. m. tube —0.68°. The
oil contains esters of n-heptilic, palmitic and acetic acids. The oil
«« S. & Co., Rep., April, 1908, p. 84.
•7 Ber., R4, p. 2981.
es Chem. & Drugg-, 02, p. 630.
•s Chem. & Drugg., 02, p.-88.
•» Chem. & Drugg., 02, p. 409. Compare also Chem. & Drugg., 59, p. 1+2;
62, '0p. Ber.,
630, 689,
34, p.985, 999.85, p. 3187.
1021;
54 PHARUAGEVTICAL REVIEW.
contained eugenol (benzoyl eugenol 70.5—71°); asarone (oxime of

asarylic aldehyde m. p. 114°); and a compound called calameon,
C15H2«02, which had been previously isolated by Soden and Rojahn.71
By the oxydation of asarone, a compound was obtained which un
ited with bisulphite of soda and had an odor like the original cala
mus oil. The percent of asarone can be determined by making a
methoxy determination. 72
The compound, calameon C15H20O2 m. p. 168 is isolated from
the high boiling fractions. It sublimes and its solutions are laevo-
gyrate. It can be oxidized to an acid C15H24O4, m. p. 153° and is
probably a compound similar to cineol.7*
Calamus oil is official in the 4th ed. of the German Pharma
copoeia with the following requirements: Sp. gr. =0.960—0.970;
soluble in alcohol.
OILS OF THE LILIACEJE.
58 a. Uganda Aloe Oil.
Upon distilling Uganda aloes with a 1 p. c. solution of potassium
carbonate, Tschirch and Klavensis73 obtained a small quantity of
an ethereal oil which solidified and had an odor of roses.
61a. Tuberoaa Oil.
From 100 grams of extract of tuberose blossoms, Polyanthes
tuberosa, S. & Co.74 obtained upon distillation with water vapor
and shaking out the 'distillate with ether, 5 grams of oil. The oil
contained methyl benzoate, but the ketone, tuberone, isolated by
Verley75 could not be separated.
By extracting fresh tuberose flowers with petroleum ether, Hesse78
obtained 0.0066 p. c. of oil and by the method of enfleurage 0.0879
or 12 times as much as by extraction with petroleum ether. This
larger quantity of oil is developed during the process of enfleurage.
Both oils contain methyl anthranilate, benzyl alcohol and esterst
principally the benzyl ester. The oil from the enfleurage contains
methyl salicylate. A comparison of the two oils is given in the
following table:
Oil by extraction. Oil by enfleurage.
dis° 1.007 1.012
an —3° 45' —3° 21'
Acid number 22 32.7
Saponification number 224 256.3
'i Pharm. Ztg., 46. p. 248.
" Ber. d. D. Phurm. Oea., 12, p. 257, 266.
" Bcr., 85, p. a194.
« Arch. d. Pharm., 239, p. 241.
»« 8. & Co., Rep., April, l!t08. p. 7.1.
« Bull. Soc. Chlm., Ill, 21, p. 307.
f Ber., 36, p. 1459.
(To be continued. )
Pharmaceutical Review
Volume 26. MARCH, 1908. Number 3.
Plant Pigments.*
By /. W. Brandel.
Botanical Classification.
In order to compare the behavior of flower pigments with the
general behavior of quinones and hydroquinones on the basis of the
quinhydrone hypothesis of pigmentation, tests were made upon a
large number of flowers. Tlte results obtained, together with the
observations, recorded in literature, and made on flowers by other
authors without the knowledge of the quinhydrone hypothesis, are
given in the following botanical classification in which the different
plants examined are arranged according to families. Those flowers
marked with an asterisk were collected with permission of Professor
Trelea-e, Director of the Missouri Botanical Garden.
As has been previously stated, the striking characteristic of the
colored quinhydrones, is the fact that they will dissolve in the
ordinary solvents to form almost colorless or slightly yellow solu
tions. Upon evaporation these solutions again yield the colored
quinhydrones. As can be seen from the accompanying tables a large
proportion of the red and blue flowers examined, yield an almost
colorless solution when extracted with alcohol. In the majority of
cases, when this alcoholic solution is allowed to evaporate, a blue
or red residue is obtained. This colored residue will again dissolve
in organic solvents forming a colorless solution.
On the other hand all yellow flowers examined, without exception,
give an intense yellow solution with alcohol from which a yellow
residue is obtained. The fact that many red and blue flowers yield
colorless solutions when extracted with alcohol, has been known for

(65)
some time,48*" but it was attributed to a supposed deoxid zing

power of the alcohol
However, the red pigments of all flowers do not behave like
quiuhydrones towards solvents. So for example, the red flowers of
Celosia cristatu (Amarantaceae) are gradually extracted by alcohol
forming a yellow solution. Upon evaporation a yellow residue is
formed. These as well as other flowers may have pigments which
are not of a quinone nature, for it is by no means to be supposed
that all flowers have as pigments the compounds previously con
sidered. Yet the behavior of the pigment in Celosia cristata can be
explained on the basis of these compounds. It is known that mono
hydroxyquinones are yellow while their metallic derivatives are red.
Inasmuch as the alcoholic solution of these flowers is strongly acid
to litmus, it can readily be seen, if these flowers contained such
a red derivative, how a yellow residue would be obtained in the
presence of the acid or acid salt. If, therefore, this free ac d were
neutralized by the addition of a few drops of a very dilute solution
of caustic potash to the alcoholic solution of the pigment a red
residue should be obtained. A red residue is actually obtained by
evaporating the alcoholic solution from the flowers of Celosia
cristata, previously neutralized with caustic alkali. Furthermore
the yellow residue from these flowers also turns red upon the addi
tion of caustic potash.
, In those cases in which a blue or red flower gives a yellow
alcoholic residue, the extraction of the pigment takes place very
slowly and the alcoholic solution is at first colored red which only
gradually disappears leaviug a yellow solution. In those cases in
which a blue residue is obtained, the extraction takes place very
readily and at once yields a colorless solution.
The blue flowers of Myosotis species ( Boragineae) blossom yellow at
first then gradually change to blue. When these blue flowers are ex
tracted with alcohol, a yellow solution is gradually formed, which has
a faint acid reaction and leaves a yellow residue upon evaporation.
If, however, a drop or two of highly diluted caustic potash solution
be added to the alcoholic solution which is then allowed to evaporate,
a blue residue is obtained. In the same way, the yellow residue
*» Eisner— Chem. Centralbl.. 3, p. 572!

*» Murquurt—Arch. d. Pharm., 56, p. 250.
PHAliMA CEUTICA L REVIEW. 07
first obtained turns blue or purple by the addition of dilute caustic

alkali.
From the examination of a large number of flowers Vogel50
drew the general c inclusion that the alcoholic solutions of the pig
ments from red flowers are always strongly acid wh n tested with
litmus paper. Blue flowers on the other hand, have in many cases
a neutral reaction or, if acid, are only faintly so. The colorless
alcoholic solutions of some blue flowers upon evaporation leave a
red residue instead of a blue. Thus there results upon the evapora
tion of the colorless alcoholic solution of the pigment from the purple
flowers of Lagerstroemia indica (Lythrariene) and Monarda didyma
(Labiatue) a red residue. By the careful addition of very dilute
ammonia or caustic aikali to the colorless alcoholic solution which
is slightly acid to litmus thereby neutralizing the free acid or acid
salts, the blue or purple color of the original flower is again ob
tained.
These behaviors of the different flowers can readily be explained
when it is remembered that the metallic derivatives of the quin-
hydrones and hydroxy-quinones are blue or purple but in the pre
sence of acids become red. Attention should also be called to the
fact that the red residues from the alcoholic solutions of many red
flowers are turned blue or purple by the addition of ammonia or a
very dilute alkali and the blue residues from the blue flowers or the
blue flowers themselves are turned red with hydrochloric acid. If
too strong an alkali is used the residue is turned green. Thus the
residue from the red geranium flowers can readily be turned to blue
by the addition of ammonia. Several red species of Salvia (Labiatae)
when held in , he vapor of ammonia, turn blue which is almost
identically of the same shade as that of such species of Salvia
which are naturally blue.
Again from the red flowers of Lobelia cardinalis (Campanulaceae)
a colorless solution with alcohol is obtained which yields a red
residue. This turns blue by the addition of caustic alkali solution
or by holding it in the vapors of ammonia.
In some cases, therefore, the blue and red species of the same
genus, is probably due to the same pigment the red being due to
the presence of neutral or acid salts or even free acids.
so SlUber. d. Aeart., Muenehen, 1879, p. 19.
A more striking illustration of the contention that a blue pig

ment is oftentimes the metallic derivative, under neutral conditions,
of a red pigment, is found in the case of the flowers of Centaurea
cyanus (Compositae). 95 percent alcohol extracts only a part of
the blue pigment of these flowers, which seems to be only sparingly
soluble in alcohol, resulting in a colorless solution which has a
neutral reaction. The flowers do not appreciably change in color
before the evaporation of this solution a blue residue was obtained.
Upon the evaporation of this solution a blue residue was obtained.
Upon the evaporation of a second portion after several months
standing a red residue resulted. The alcoholic liquid was now slightly
acid. Stein51 has found considerable quantities of calcium in these
flowers.
Another characteristic of the quinhydrones is the fact that they
are very readily reduced to the colorless hydroquinones which in
turn readily absorb oxygen resulting in the reproduction of the
colored compound. Many red and blue flowers especially those
which give the quinhydrone test (colorless solution in alcohol) are
readily decolorized when held in an atmosphere containing a small
percent of sulphur dioxide.
Thus the purple alcoholic residue from the flowers of the purple
pansy ( Violaceae) become colorless when held in an atmosphere of
sulphur dioxide but regains the purple color gradually when allowed
to stand in the air. In the presence of moisture the restored color
is red in stead of purple, due to the fact that some of the sulphur
dioxide is retained by the moisture and the resulting acid turns the
purple residue to red. None of the yellow flowers examined, are at
all effected by even strong sulphur dioxide vapors.
Some flowers contain pigments of more than one color. For
example the purple-red flowers of Dahlia variabilis (Compositae)
contain a yellow and a red pigment. If these flowers are extracted
with alcohol for some time, a bright yellowish-red solution is ob
tained which upon evaporation gives a dark red residue. If how
ever, the flowers are allowed to stand in contact with the alcohol
for only a few minutes and the alcoholic solution then poured off, a
light yellow solution is obtained which yields a dark red residue.
Upon extraction with a second portion of alcohol, a bright yellow
solution is obtained which yields a yellowish-red residue.
« Journ. prakt. Chem., 89, p. 495.
Color of Color of Color of
Observer. flower. ale. boI. residue.
Amarantaceae.
Celosia cristata Brandol red yellow yellow
" i Vogel red
Celosia plumosa Brandel red yellow yellow
Amarylliueae.
Leucojum vera um 2 Stein
Apocynaceae.
Vinca minor3 Marquart blue
" * Vogel blue
Aroideae.
Arum divaricatum5 Marquart brown
Arum dracunculus, L.6 Marquart brown
A RISTOLOCHIACEA E .
Aristolochia glauca 7 Marquart brown
ASCLEPIADEAE.
Asclepias tuberosa* Marquart orange
Asclepias currasavica* Marquart orange
BORAGINEAE.
Anchusa officinalis™ Hunefeld
Borago officinalis 10 Hu nefel d
" Vogel blue
" 12 Vogel blue
is Vogel white
Cynoglossum officinale 10 ...Hunefeld blue colorless
i*... Vogel blue
Cynoglossum omphalod. ,0Hunefeld
isHunefeld
Echium vulgare 1 0 Elsner red decolorized red
" it Vogel blue
" is Hunefeld
Echium pyrenaicum 10 Hunefeld
i Alcoholic solution Is strongly acid (Sltzb. d. Acini. Milnrhen, 1879, p. lit.)

» ContainH glucoslde rutin which yields quercetln (Journ. pr. Chem., 85, p. 851.)
3 Aqueous solution turneil lilac with boric acid (Arch. d. Pharm. 56, p. 241).)
* Alcoholic solution has faint acid reaction (Sltzb. d. Acad., MUnchen, 1879,
p. li>.)
s Color due to violet pigment and chiorophyll (Arch. d. 1'harm. 50, p. 258).
• Arch. d. Phurm. .">*>, p. 258.
7 Color due to chiorophyll and a blue pigment reddened by acid (Arch. d.
Pharm. 56, p. 258).
s Contains yellow and a red pigment (Arch. d. Pharm. 56, p. 257).
t09 Contnins yellow Uhem.
and red9, pigment
.Tourn. f. prakt. p. 217. (Arch. d. Pharm. 56, p. 257).
!t Color not changed by ammonia (Sitzb. d. Acad MUnchen 1879, I, p. 17).
■z Alcoholic solution is acid (Sltzb. d. Acad. MUnchen 1879, p. 19).
t3 Alcoholic solution has acid reaction (Sitzb. d. Acad. MUnchen 1879, p. 19).
i* Has faint acid reaction (Sltzb. d. Acad MUnchen 1879, p. 191.
is Yields colorless solution with turpentine (Journ. pr. Chem. Hi. p. 68).
ts Yellow precipitate with lead acetate (Chem. Centralh. 3, p. 570).
t7 Has faint nHd reaction. Flowers arc red then orange to blue (Sitzb. d.
Acad. MUnchen 1K79. p. 19).
ls and i». Journ. I. prnkt. Chem. 9, p. 2a8.
Observer. flower. ale. sol. residue.
Heliotropus peru vianum, L...Brandel blue yellow light blue
a"Vogel blue
Myosotis palustris, L Brandel blue yellow yellow
" 2> Vogel blue
Myosotis versicolor22 Marquart blue
Nonea rosea23 Marquart violet
1'ulmonaria angustifolia2*. ..Marquart red
Pulmonaria officinalis2* Marquart red
Cacteae.
Cactus phyllanthus2^ Buchner blue-red colorless blue
Cactus ffagelliformis2* Buchner blue-red colorless blue
Cactus speciosus20 Vogel red colorless red
Calycanthaceae.
Calycanthus floridus27 Marquart brown
Campanulaceae.
Campanula ranunculoides2H.\Toge\ violet
" 2B. Vogel violet
Campanula glomerata2n Vogel blue
Campanula rotundifolia29 ....Vogel blue
Campanula granditiora30 Hunefekl
Campanula perstcifolia3i : Vogel blue
Campanula pyramydalis3i Vogel blue
Lobelia erinus32 Vogel blue
Lobelia cardinalis, Ij Brandel red yellow red
Lobelia syphilitica...., Brandel blue colorless blue
Capparideae.
Capparis spinosa33 Rochleder yellow
Capmfoliaceae.
Sambucus nigra3i Hunefeld white
Viburnum opu/fis,var.ro.sevi^Murquart white
Viburnum opulus30 Filhol white
20 HuB 22.
faintFlowers
acid reaction fSlub. d. Acad. Muenchen 1879,(Arch.
p. 19).
2t and are first yellow then change to blue d. Pharm. 50,
p. 260).
2s Solution turned red with boric acid (Arch. d. Pharm. 56. p. 263>.
2* Changes to blue upon fading ( Arch. d. Pharm. 50. p. 263.)
25 llesidue Is turned green with alkalies and red again with acids (Chem. Cent-
ralbl 7, p. 580).
'« Ann. d. Chem. 5, p. 20.".
27 Cross section shows middle layer of chiorophyll and two outer layers of
violet
2B pigment (Arch.byd. ammonia
Pharm. 5<1. p. 258).
Turned green (Sitzber. d. Acad. Muenchen 1H70. I, p. 17).
2» Alcoholic solution hns neutral reaction ISitzb. d. Acad. Muenchen 1879,
p. 19).Journ. f. prakt. Chem. 9. p. 217.
st Alcoholic solution has faint acid reaction (Sitzb. d. Acad. Muenchen, 1879,
p. 19).
32 Alcoholic solution has neutral reaction (Sitzb. d. Acad. Muenchen 1Si9,
p. 19).
ss Buds contain quercetin glucoside (Chem. Centralhi. 3o, p. 100).
s* Contains copper (Journ. f. prakt. Chem. 16. p. 84).
s» Changed to red on w ilting (Arch. d. Pharm. 50, p. 202).
»« Changed to yellow with ammonia (Compt. rend. 89, p. Iil4).
Observer. flower. ale. HOl. residue.
Caryophyxlaceae.
Dianthus caryophyllus Brandel red pink red
Diantbus species37 Eisner red pink red
Dianthus cartham.3* Vogel red
Dianthus carthusianorumM.. Vogel red
Lychnis chalcedonin 40 Elsner red colorless red
" " 41 Vogel red
Hunefeld red
" " 43 Marquart red
Suponarin officinalis Brandel rose colorless pink
Silene armeria*3 Marquart red
44 Vogel red
Chenopowaceae.
Artriplex hortensis*^ Hunefeld red
" " 46 Schnetzler red
Compositae.
Achillea millefolium*1 Vogel rose
Arctotis grandiflora*>* Marquart orange
Anthemis tfnctoria 4T
" " 4» Vogel white
" " 50 Vogel yellow
Aster Brandel blue yellow pink
" Brandel dark blue colorless purple
" Brandel red yellow red
" Brandel white yellow yellow
" Brandel purple yellow purple
Aster, wild Brandel white colorless yellow
" " Brandel blue colorless yellow
Astersi Elsner red decolor. purple-red
Aster chineusis7'- Vogel violet
R2 Vogel blue
Aster mo vaeangelae 52 Vogel red
Aster tenellu53 Vogel violet
37 Anueoux Holutlun gives blue-green prec. with lend acetate and violet precipi
tate with line chioride (Chem. Centrnlbl. 3. p. 510).
»» Not changed by nmuiouia (Sitzh. d. Acad. Muenchen 1870. I. p. 17).
39 Alcoholic noiudon has Htrong acid reaction (Sitzb. d. Acad. Muenchen 1879,
p. 19).
*o Chem. Centrnlbl. a, p. 572.
*i Same to* 39.
*2 Journ. f. prakt. Chem. 16, p. 73
*3 Aqueous solution 1H turned purple red with zinc chioride but no precipitate
1b formed (Arch. d. Pharm, 50. p. 2">2(.
44 Same as 39.
4s Journ. f. prakt. Chem. 10, p. 74.
*« Aqueous solution turned green with borax (Jnhresb. u. d. Fortsch. d. Chem.
1877,
*7 p.Solution
925). has acid reaction (Sltzb. d. Acad. Muenchen 1879, p. 19).
4B Arch. d. Fharm. 50, p. 257.
49 Turned yellow by ammonia (Sltzb. d. Acad. Muenchen 1 S70. I, p. 17).
30 Not changed by ammonia (Sltzb. d. Acad. Muenchen 1870, I. p. 17).
3t Solution gives green prec. with lead acetate (Chem. Centrnlbl. :t. p. 570).
01 Not changed by ammonia (Sltzb. d. Acad. Muenchen 1870, I, p. 17).
33 Turned green hy ammonia (Sltzb. d. Acad. Muenchen 1870, 1, p. 17).
Color of Color ol Color ol
Observer. flower. ale. Bol. residue.
Bellis peren nis 5* H lasi wetz
Calendula officinalis™ Wirth
" 38 Kirchner
" " « Marquart orange
" " sT Hunefeld orange
'• " 58 Schnetzler yellow
Cla lliopsis birolor** Marquart yellow
Callistephus chinensis Brandel rose colorless pink
Brandel 1 ight blue colorless pink
" " Brandel blue colorless blue
" " Brandel crimson colorless red
Cen tauren gymnocarpa Brandel blue colorless yellow
Centaurea cyanus Brandel blue colorless pink
Centaurea cyanuss9 Hunefeld
" " 8o Stein blue
oi Nietzki blue
" 82 Vogel violet
Centaurea jacea 62 Vogel red
Cen ta u rea sea biosa 8s Vogel purple red
Cichorium intybus Brandel blue colorless blue
Cichorium in tyhus 64 Vogel blue
" •» Nietzki blue
" " 86 Vogel blue
Cineraria cruenta6* Marquart blue colorless blue
Cardnus speciesoa Eisner red decolor. red
Chrysanthemum pu/Jgare69...Filhol white
Coreopsis bicolor70 Vogel yellow
Caphea vinosa 71 Vogel red-violet
Cuphea miniata"- Vogel red
Cos mos Brandel purple pink purple
Da hlia variabilis Brandel crimson yellow red
Brandel red yellow red
Brandel yellow yellow yellow
« Contains quercetln (Ann. d. Chem. 112, p. 96.)
«5 ContaluH extent of cholesterin anil a hydrocarbon (Bot. Centralbl. Belh. 8,
p. 2lT.).
5« Contains. cholestrin esters (Bot. Centralbl. 52. p. 229).
s7 Contains iron and man .nnese (Journ. ur. Chem. 16. p. 84).
ss Not changed tw bornx solution (.lahresb.' 11. d. Fortschr. d. Chem. 1877,
p. 926).
«» Journ. pr. Chem 9, p. 217).
so Turned red with hvdi ochiorlc acid. Contains much calcium (.lourn. pr.
Chem. Hit, p. 495).
«i Contains glucoside (Arch. d. Phurm. -08. p 327).
«« Not changed by ammonia (Sltzh. d. Acad. Muenchen 1871), I, p. 17).
«3 Solution has acid reaction (Sluh. d. Acad. Mtfenchen 1S79, p. 19).
«* Solution has faint reaction (Slttb. d. Acad. Muenchen 1879. p. 19).
«5 Contains glucoside which yields a prodnct M. P. 250—255° (Arch. d. Pharm.
208.B«p.Turned
H27). eree i by ammonia (Sltzh. d. Acad. Muenchen 1870. p. 17).
«t Solution is turned lilac with boric acid (Arch. d.. Pharm. 56, p. 250)
«« Solution gives brown prec. with zinc chioride, greenish prec. with lead
acetnte (Chem. Centralbl. .'!, p. 570).
«» Turned yellow by ammonia (Compt. rend. 39, p. 194).
70 Not changed by ammonia (Sltjth. d. Acad. Muenchen 1 ><70, I, p. 17).
'i Turned blue b ' ammonia (Sltjb. d. Acad. Muen hen 1870. I. p. 17).
73 Solution has strong acid reaction (Sltzb. d. Acad. Muenchen 1879, p. 19).
Dahlia variabilis Brandel white yellow yellow
" " Brandel purple-red light red dark red
Dahlia13 Eisner red colorless dark violet
Gazarria ringens 74 Marquart
Helianthus annmis"'5 Fremy yellow yellow yellow
Helichrysum monstrosum
luteum Brandel yellow yellow yellow
salmonosn, Brandel pink yellow yellow
roseum Brandel pink colorless red
roseum (disk f|or.) Brandel yellow yellow yellow
purpurea Brandel purple pink purple
Helichrysum bracteatum16. ..Rosoll yellow
Helichrysum arenarium'6 Rosoll yellow
Serratula species17 Eisner red colorless red
Tanacetum vulgare1* Hunefeld
" " 79 Leppig yellow
Zinnia elegans (scarlat gem). Brandel red yellow yellow
" " salmonea
rosea Brandel red yellow ( pink
" " carminea Brandel carmine yellow purple
" " aurea Brandel yellow yellow yellow
" " purpurea Brandel purple yellow brown
Zinnia elegans60 Vogel red
CONVOLVULACEAE.
Ipomoea purpurea. L Brandel purple colorless purple
Ipomoea mutabilis*i Marquart blue
Con volvulus tricolor*2 Hunefeld
Convolvulus arvensis*3 Vogel rose
Convolvulus mauritianuss* .. Vo«rel blue
Convolvulus bicolor** Vogel blue
Symphytum officinale™ Vogel red
73 Solution gives dark green prec. with lead acetate (Chem. Centrall)!. 3. p. 572)
71 Arch, d Pharm. 56, p. 238).
ts Journ. de Pharm. (a) 25, p. 249.
7« Contains hellchrysln (Monatsh. f. Chem. 5, p. 94).
77 Chem. Centrall)!. :!. p. 572.
7s ContalnH iron (Journ nr. Chem. 16, p. 84.
s0 Solution has *troncr(Pharm:
7» Contains tunecetln ZiHchr.(Sitzb
f. KuHsI. 21. p. Muenchen
141. 169, 1879,
19a). p. 19).
acid reaction d. Acad
st Flower wax at fiist white (Ar"h. d. Pharm 56, p. 262).
«3 Journ.
s3 Alcoholicf. prakt.
solution,'hem. 16, p. 69.
has strong acid reaction (Sitzb. d. Acad. Muenchen 1879.
p. 19).
« Has faint acid reaction (Sitzb d. Acad Muenchen 1879, p. 19;
s5 Has neutral reaction (Sit/.b. d. Acad Muenchen 1879, p 19).
( To he continued. )
Percolation.*
By J. W. Brandel and Ed. Kremers.

Sackett, C. "W. 1901.
Automatic percolator cut-off.
Fig. 4.1. Automatic cut-off.

Tht' automatic cut-off shown in illustration is recommended for the pur
pose of cutting off the flow of percolate when a certain portion has accum
ulated in the receiver.
A is a lube arranged to move like a scale beam on
E, the support and is connected by
a rubber tube to the percolator.
C is a v al containing one-half ounce of mercury.
D is an empty viul attached to one arm of A. To operate, fill bottle
containing the float D, with water equal to the amount of percolate to be
reserved. Adjust the float so that the tube .4 is nearly horizontal. Empty
the bottle and allow percolation to begin. As soon as 1) flouts, the per
colate will be diverted into the other bottle.
• Continued from page 55.
Andrews, E. A. 1902.
Preparation of liquid extract of belladonna B. P. by a process
of repercolation.
Pharm. Journ., April 1902, p. 336.
Stedem, P. W. E. 1902.
Manipulation in case of resinous drugs.
Bull. Pharm., 1902, p. 235. [Proc. A. Ph. A., 50, p. 682.]
More specific directions for percolating resinous and oleoresinous drugs
in preparing tinctures and fluidextracts.
Linton, W. H. 1903.
Percolation as applied to the liquid extracts of the B. P.
Pharm. Journ., 1903, p. 389, 420, 457. [Proc. A. Ph. A., 51,
p. 622.]
A review of the history of percolation as applied to the extraction of
drugs and a record of the results of a series of experiments on the liquid
extracts of coca and cimicifuga and liniment of aconite. The general con
clusion is drawn that two-thirds of the totul soluble matter is extracted in
the weak percolates and is consequently subjected to a fairl.v high tempera
ture during concentration. A reduction in the amount of menstruum used
in moistening the drug is recommended.
Rnhle, H. F. 1903.
Percolator support.
Proc. Pa. Pharm. Assoc., 1903, p. 145. [Proc. A. Ph. A., 52,
p. 485.
A simple wall device for a permanent percolator support.
Hooper, E. S. 1904.
Apparatus for collecting percolate
in fractions.
Pharm. Journ.. July 1904, p. 140.
[Proc. A. Ph. A., 53, p. 506.]
The apparatus consists of
A, a narrow glass tube fitted into
B, a f/-tube, the other limb of which
contains n gloss tube to serve as a pressure
tube.
P, the percolator is connected to the
lowest side tube. When C-tube // is filled
the percolate will puss into the 2nd Fig. 4.8.
{/-tube, etc. Percolation Apparatus.
Schmitt, L. 1904.
Percolation vs. maceration.
Journ. pharm. chim., 1904, Nos. 1—4. [Proc. A. Ph. A., 52,
p. 483.]
A report, on the results of a series of experiments on the relative efficiency
of maceration and percolation, Percolated tinctures formed larger precipi
tates than those made by maceration.
Progress in Alkaloidal Chemistry during the Year 190(>.*
By H. M. Gordin.
Caffeine.
As is well known xanthine and its methyl derivatives, heteroxan-
thine, paraxanthine, theophylline and theobromine, can be converted
into caffeine (trimethylxanthine). E. Fischer and F. Ach show that
vice versa by successively splitting off methyl groups from caffeine
the alkaloid can be converted either into xanthine itself or any of
its methyl derivatives.
When 8-chlorcaffeine (I) is heated with phosphorus pentachloride
CH„.,N| aCO
I ru
una
»C0 5C.tN<
I jsC.Cl
CHa.sN 4C.0N7
8-Chiorcaffelne.
(I)
using phosphorus oxychloride as a solvent or when chlorine is
passed into melted caffeine 3'.8-dichlorcaffeineis formed
CH3.NI CO
I /Ha rH
CO C.N<
I ll )C.C1
CHaCl.N C.N/
3'.8-Dlch1or caffeine or
S-fhiiirmethyl-S-chliirparaxan thine.
(ID
which is purified by pouring off from the unattacked 8-chlorcaffeine,
evaporating to dryness, dissolving residue in chloroform and, after
washing the solution with water to remove traces of the phosphorus
chlorides, evaporating the solvent to a thin syrup. On mixing this
syrup with dry ether and evaporating the solvent the dichlor com
pound separates out in crystals and can be washed free from adhering
syrup by means of benzene. The compound is very difficultly soluble
• Continued from pagt' 4 H.
in cold water but easily soluble in chloroform, benzol, acetone and
acetic ether and gives the murexide reaction. In the mother liquor
of the dichlor compound there seems to be a small amount of a
trichlor compound.
When the 3'.8-dichlorcaffeine is boiled with water formic aldehyde
and hydrochloric acid are given off and on cooling 8-chlorparaxan-
thine separates out in crystals.
(;Hs.N CO PH
CO C.N<
NH—C.N^
S-Chlorpuraxnnthlne.
(Ill)
It can be recrystallized from hot water and dried at 100°. By
reduction it can be converted into paraxanthine.
If the 3'.8-dichlorcaffeine be boiled- with methyl alcohol instead
of with water :i'.8-methoxy-8-chlorcaffeine is formed
CHs.N CO CHs
I i /
CO C.N<
I I >C.C1
CHs.O.CH2.N C.N^
S'.Methoiy-8-rhiorcafleine.
(IV)
When heated with hydrochloric acid (1.19) to 100° the methoxyl
group is eliminated and 8-chlorparaxanthine (III) is formed.
On passing chlorine into a solution of caffeine in nitrobenzene or
phosphorus oxychloride at 90—100°, evaporating the solvent under
reduced pressure and recrystallizing the product from methyl alcohol
the alkaloid is transformed into 7'.8-dichlorcaffeine
CHs.N—CO CH2C1
I I /
CO C.N<
I I )C.C1
CHs.N C.N^
7'.8-Dlchiorcaflelne.
(V)
The 7'.8-dichlorcaffeine differs from the 3'.8-dichlorcaffeine (II) in
that the former is not affected by boiling methyl alcohol. Boiling
with water converts the 7'.8-dichlor-compound into 8-chlortheophyl-
line with the elimination of hydrochloric acid and formic aldehyde
CHo.N CO
I I
CO C.NHX
I II >C.CI
CHs.N C.N^
H-Chiortbeophylllne.
(VI)
By reduction the 8-chlortheophylline can be converted into theo-
phylline.
On heating the 7'.8-dicblorcaffeine with sodium ethylate, filtering
off from the sodium chloride and cooling the liquid diethoxycaffeine
separates out in needle-shaped crystals.
CH..N—CO CH2.0C2H8
CO C.N<f
| I >C.O.C2H5
CHs.N C.N^
7'.-Diethoxycaffeine.
(VII)
The compound is insoluble in hot dilute sodium hydroxide but soluble
in hot dilute hydrochloric acid, benzol and glacial acetic acid.
On heating 7'.8-dichlorcaffeine with a solution of chlorine in
phosphorus ox\-chloride to about 160° underpressure, concentrating
the liquid at 45° under a pressure of 15—20 mm. and dissolving the
residue in hot benzol tetrachlorcaffeine was obtained which separated
out in yellowish crystals upon concentration of the benzol solution.
It was purified by shaking its solution in warm ether with animal
charcoal, concentrating the ethereal solution and then coolingwith ice.
CI.CH..N—CO CH2C1
CO cn/
I I >.C1
l'.3'.7'.S-Tetraohiorcaffcine.
(VIII)
The tetrachlorcaffeine is easily soluble in acetone, benzol, glacial
acetic acid and alcohol. It is also soluble in hot water but the
aqueous solution is soon decomposed under elimination of formic
aldehyde. It is insoluble in dilute alkali.
By warming the tetrachlorcaffeine with sodium • methylate dis
solved in absolute methyl alcohol, neutralizing the liquid with acetic
acid and evaporating to dryness tetramethoxycaffeine was obtained
as a crystalline mass which was recrystallized from hot water. It

was purified by repeated recrystallisation from methyl alcohol and
ether. It is easily soluble in glacial acetic acid, hot alcohol, benzol
and chloroform.
CHg.0.CHS.N—CO ,CH«.aCH|
f° 7>0.CH3
CHs.O.CH2.N C.N/
Tetramethoxycaffeine.
(IX)
On boiling a solution of tetrachlorcaffeine (VIII) in a mixture of
two volumes of glacial acetic acid and one volume of water for ten
hours formic aldehyde and hydrochloric acid are eliminated and
8-chlorxanthine crystallizes out upon concentrating the liquid. In
order to complete the reaction it was necessary to add more glacial
acetic acid and continue the boiling for another hour while passing
a strong current of steam.
NH CO
I !
CO (J.NHs
I II >.C1
NH C .
8-Chiorxan thine.
The chlorxanthine was purified by converting it into the am
monium salt which crystallizes well, then recrystallizing the ammoni
um salt from very dilute ammonia and decomposing the salt in
aqueous solution by acetic acid.
On boiling the chlorxanthine with strong hydriodic acid (1.96)
and phosphonium iodide the hydriodide of xanthine was prepared
from which free xanthine was liberated by ammonia.
(Ber., 1906, p. 432.)
Quinine.
According to H. Lacroix neutral quinine formate commences to
lose formic acid at 50° and the loss is complete at 95° the residue
being pure quinine soluble in ether chloroform etc. Dissolved in
water the neutral salt dissociates into formic acid and basic quinine
formate giving a solution of a decidedly acid reaction.
The basic quinine formate (quinoform) is not dissociated even
by boiling water and melts at 109° (not at 132° as previously re
ported) with decomposition. The specific rotation of the basic salt
80 PHARMACEUTICAL REVIEW.'
obtained from a one per cent solution at 20° is [a]n20 = —144.2°

(not —141.1° as previously reported.)
(J. phann. chim., 1906, p. 493.)
E. Comanducci and L. Pescitelli have prepared the sulphur ethers
of quinine and einchonine by heating the alkaloids in chloroformic
solution with phosphorus pentasulphide. After filtering off from the
excess of the latter and removal of the chloroform by distillation
the product was recrystallized from alcohol.
Thioquinine, (C2oH2sN20)2S, forms a yellowish microerystalline
powder coagulating at 140—142° and melting at 150—152°. It
has an odor of onions and is soluble in alcohol or chloroform but
insoluble in ether. It gives fluorescent solutions when dissolved in
dilute sulphuric or nitric acid, and the solutions retain the same
odor. Alkalies reprecipitate the base from these solutions. It gives
the thalleioquin reaction and when threated with chlorine, ammonia
and potassium ferrocyanide assumes a red color. It also gives the
herapathite reaction.
Thiocinchonine, (C19H2iN2)2S, was prepared by the same method
as thioquinine. It forms an amorphous powder of a decided
alliaceous odor, decomposes without melting when heated to about
190— 192°, is soluble in alcohol or chloroform but insoluble in ether
or water. (Gazz. chim. ital., 1906, p. 781).
Two formates of quinine were prepared by P. Guigues, a neutral
formate and a basic formate. The neutral salt, C2oH24N2C>2(CH202)2,
was made by dissolving quinine in excess of dilute formic acid and,
after neutralizing with dilute ammonia, concentrating the liquid on
a water bath. The salt melts below 100° and loses some formic
acid when kept in the neighborhood of that temperature. It is
easily soluble in water and the solution is neutral to phenolphthalein
but is both acid and alkaline to litmus. The basic formate,
C20H24N2O2.CH2O2, was made by dissolving quinine in the theoretical
amount of formic acid and adding a strong neutral solution of
ammonium formate. The basic salt is stable in the air, is not
altered when heated to 100° and dissolves in less than 20 parts of
water. (J. pharm. chim., 1906, p. 301.)
Solanine.
M. Wintgen has assayed a large number of various samples of
potatoes for solanine. The method consisted in extracting the
PHARMACEUTICAL REVIEW. SI
potatoes with alcohol, evaporating the solvent, dissolving the residue

in acidulated water and precipitating the solanine with ammonia.
Both healthy and sick potatoes were examined. Experiments were
also made in order to establish whether sola nine is developed by
prologed keeping or by certain bacteria as is claimed by Weil and
Schnell (Arch. F. Hygiene, 1900, 33, p. 330; Apoth. Ztg., 1898, 13,
p. 775, and 1900, 15, p. 133). The results obtained were as follows:
The amount of solanine in different samples varies between very
wide limits but is much smaller than is generally given in literature.
(The highest amount obtained was a little more than 100 milli
grams of solanine per kilogram of potatoes). Most of the solanine
is present in the outer parts of the tubers greatly diminishing to
wards the center. An increase of solanine by keeping does not take
place. Sick potatoes do not contain more solanine than healthy
ones. Solanine is not formed by bacteria.
From these results the author draws the conclusion that cases
of poisoning by potatoes must be due to some other causes, not to
the small amount of solanine contained in them.
(Arch. Pharm., 1906, p. 360.)
G. Oddo and A. Colombano find that the only criterion of purity
for solanine obtained from Solanum sodomaeum is the uniform pris
matic shape of crystals which can be observed under the microscope.
The purification of the alkaloid is effected by first recrystallizing it
from 80% alcohol, then dissolving it in dilute sulphuric acid and
reprecipitating with pure sodium hydroxide. The alkaloid is then
again repeatedly recrystallized from 80% alcohol till uniform prisms
are obtained. It has no defimte melting point undergoing gradual
decomposition when heated. Owing to the very low percentage of
nitrogen it contains its formula cannot be established with certainty
by analysis. While according to former analyses the formula was
given as, C23Hs9NO6, later results correspond better to C27H47NO9.
(Gazz. chim. ital., 1906, n, p. 522.)
Sparteine.
According to renewed experiments by M. Scholtz the results ob
tained in a previous investigation of the author in collaboration
with P. Pawlicki (Arch. Pharm., 1904, 513) are not quite correct.
While sparteine is undoubtedly a diacid base it is nevertheless
very difficult to combine it with two molecules of alkyl halides.
When heated with ethyl iodide in alcoholic sotation the alkaloid is

converted not into the diiodoethylate, C1sH2oN2lCsHoI )a, but into
the hydriodide [of the monoiodoethylate. C15Ha6N2.C2H5I.HI (Mills,
Ann., 18(i3, p. 71). The tendency of sparteine to split off hydriodic
acid from alkyl iodides is so strong that when treated with some
alkyl iodides nothing but the hydriodide of sparteine is formed.
Tims, while at ordinary temperature sparteine slowly combines with
ethyl iodide to an addition product, the compound formed at 150°
consists of sparteine hydriodide alone. Whether the iodoethylate of
sparteine is treated with methyl iodide or the iodomethylate is
treated with ethyl iodide there is no reaction at ordinary tempera
ture while at higher temperatures decomposition takes place and
sparteine hydriodide alone is produced. With some alkyl iodides
sparteine does not combine at all. Thus, when treated with amyl
iodide or the methyl ester of iodoacetic acid only sparteine hydriodide
is formed. With benzyl iodide sparteine combines at ordinary tem
perature to an addition product, C15H26N2.CfiH5.C2H5!, but at the
same time a small amount of sparteine hydriodide is also formed.
When the iodobenzylate is warmed with the methylester of iodoacetic
acid again only a hydriodide is produced.
While it is difficult to make both nitrogen atoms of sparteine
combine with alkyl iodide there are nevertheless two compounds iu
each of which both N atoms are linked to a halogen atom and to
four organic radicles. One is the previously described addition product
of sparteine and ortho-xylylene bromide, C15H26N'.C6H4(CH2Br)a. In
this compound both N atoms are pentuvalent as showu by the
following formula:
Br
This composition of the compound was shown by an analysis of

the platinum compound obtained by converting the bromide into
the corresponding chloride by means of silver oxide and hydrochloric
acid and then precipitating with platinum chloride.
The other compound in which both N atoms are pentavalent is
the diiodomethylate obtained but not analyzed by Moureu and
Valeur (Compt. rend. 140, pp. 1601, 1645; 141, pp. 49, 117, 261).
The composition of this compound, too, was shown by an analysis
of the platinum salt.
The existence of two isomeric monoiodomethylates and two
isomeric monoiodoethylates of sparteine is explained by Moureu and
Valeur by assuming the isomerism to he of a stereochemical nature.
They show that the hydriodide of either of the isomeric monoiodo-
alkylates when heated to 2-32° loses alkyl iodide and yields one and
the same sparteine hydriodide, hence in both isomerides the alkyl
iodide must be linked to one and the same N atom and the isomerism
must be due to stereochemical difference. That the formation of one
and the same hydriodide cannot be accounted for by assuming that
at the high temperature of the reaction the hydriodic acid changes
its place is shown by these authors by the fact that when the
hydriodide of one of the isomeric monoiodomethylates is heated
with excess of methyl iodides to 135° only there is also formed a
small amount of the hydriodide of the other monoiodomethylate.
As at this comparatively low temperature the hydriodic acid is not
apt to change place the hydriodide of the second monoiodomethylate
cannot be formed except by a stereochemical transformation. In
this the author of this paper does not agree with Moureu and Valeur.
He thinks that the isomerism is due to a difference in position of
the alkyl iodide with regard to the N atoms and that both at 232°
and 135° the hydriodic acid changes its place.
According to Moureu and Valeur sparteine has one or the other
of the following formulae
CH CH CH CH
and the supposed stereoisomerism is ascribed by them to the penta-

valency of nitrogen in the iodoalkylates. But, as it was shown by
the author in the case of couiine and conhydrine, only such derivatives
of these bases form isomeric iodoalkylates as contain an asymmetric
N atom, i. e., an N atom linked to five different radicles. This con
SI PHARMACEUTICAL REVIEW.
dition not being fulfilled in either of the above formulae the isomerism
cannot be due to a stereochemical difference in the N atoms.
Comparative physiological tests of the sparteine alkyl halides
showed that while they exert a favorable influence upon the heart
they have an injurious effect upon the respiration.
(Arch. Pharm., 1906, p. 72.)
Thalleioquin.
According to H. Fiihner the thalleioquin reaction given by
quinine, cupreine and other derivatives of para-oxyquinoline depends
upon the formation of a dichlorketone compound. This is shown by
the fact that dichlorketoquinoline, obtained by the action of chlorine
upon the hydrochloride of paraoxyquinoline in aqueous solution,
gives the thalleioquin reaction when treated with ammonia, 'while
OH C.CIa
>\ C /\
HC/ v' \('°
f ■ , I
I s I
HCv\ /\ CH
\/ C \ , '
N CH
Diohlurketoqulnollne.
other chlorine derivatives of para-oxyquinoline do not give the
re iction with ammonia. The blue compound formed by the action
of ammonia on the dichlorketoquinoline the author names thalleio-
quinoline and the derivatives of this compound obtained from
quinine, cupreine, quinidine, etc., are named thallioquinine, thalleio-
cupreine, thalleioquinidine respectively.
A compound similar or possibly even identical with thalleio-
quinoline seems to be formed by treating 5,6-quinoline quinone with
ammonia
CO
5, 6-Oulnollne<iulnoDe.
The formula of thallioquinoline seems to be C1sHt+NiC^. As
aminooxyquinoline assumes a green color when heated it is possible
that the compound is [under these conditions oxidized to thalleio-

quinoline.^2C9HsNa0 + 0 = C18H14N4O2 + Ha0
C.NH2
\C.0H
N
Auilnooxyqulnollne.
The conversion of dichlorketoquinoline into thalleioquinoline can
be effected only by ammonia, not by any other alkali.
The formula of thalleioquinoline is either that of an indamine (I)
or that of an oxazone (II)
C—O.NH4 CO
(
! I j T J
CH CH N
DlqulnolyMndamlne-ammonla.
(I)
C-O.NHi 0 C
/\ /\\C=N 0/ y\ /\
I
\ X\ /OH HC
V \/ x/ \/
N CH CH N
Dlqulnolyloxazone-ammonla.
(II)
In both formulas the nitrogen atom which links the two quino-
line molecules is assumed to be in the para-position to the nitrogen
atom of the quinoline complex. This assumption is made owing to
the similarity between thalleioquinoline and the quinone amidedyes.
When thalleioquinone is warmed with sodium or barium hydrox
ide there is an evolution of ammonia which shows that thalleio
quinoline, like murexide, is an ammonium salt (see Ann. 1904, p. 33."}).
Owing to certain similarities in the behavior of thalleiquinoline
with that of the indamines the author considers the indamine formula
(I) as the more probable one. (Arch Pharm., 1900, p. 602.)
86 PHARMA CEUTICA L REVIEW.
Thebaine.
M. Frennd has sueceded in converting thebaine into codeine. On
treating thebaine with bromine in chloroformic solution a hydro-
bromide of a brominated base in crystalline form is found among
the products of the reaction which corresponds to the formula
C1sHôBrNOi.HBr. The true base underlying the hydrobromide has
the formula C1sHjsBrNOs, i. e., contains one molecule H2O less than
it does in the salt. In the same way on converting the base into
the hydrochloride the salt has the formula, C18H20BTNO4.HCl, while
the base liberated from the hydrochloride corresponds to C1sH1s-
BrNOs.
The new brominated base contains one methylimide and only
one methoxyl group showing that, as in the conversion of thebaine
into thebenine or morphothebaine, in the transformation of thebaine
into the brominated base one of the methoxyl groups of thebaine is
eliminated.
That the brominated base is neither monobromthebenine nor
monobrommorphothebaine is shown by the fact that it is insoluble
in alkalies while thebenine and morphothebaine containing a phenolic
()U group are both soluble in alkalies. The brominated base reacts
with hydroxylamine forming a crystalline oxime with elimination of
bromine. Most probably the reaction is as follows:
1. CisHisBrNOs + H2N.OH = CisHi8Br.NO:> : N.OH + H20
2. CisHisBrNO» : N.OH + H20 - C)8His(OH )N02 : N.OH + HBr
That the brominated base is really a ketone is also shown by the
fact that nascent hydrogen converts it into codeinone identical with
the codeinone previously obtained by Ach and Knorr (Ber. 1903,
p. 3067).
CisHisBrNOa + 2H = CiaHi9NOs + HBr
The brominated base is therefore monobromcodeinone and its
formation from thebaine can be explained by assuming that at first
the double binding of the ring containing the nitrogen bridge is
removed and two atoms of bromine are taken up forming thebaine
di bromide. The dibromide then loses one molecule methyl bromide
and changes to monobromcodeinone. The bromcodeinone when
treated with nascent hydrogen is converted into codeinone. As
according to Ach and Knorr codeinone can be reduced to codeine
the above reactions enable us to convert thebaine into codeine.
The reactions taking place in the conversion of thebaine into
codeine can be represented by the following scheme:
CH«.0/ CHs.O/
I V x- \ A
v \
o I 1
CH II
C,V ICH C ■CH
CHs.O 'CH CHs.O.BrC\^^/CH

< II CH.Br
Thebulne Dibromthebalne
/\
CH:,.() CH..O/
\
\v \
V ICH + tH*Br ° IcH
A / /\ /
C|\, CH /
V v ICH
0:Cs HO.HC\ /CH

\/
UH.Br CH.Br
Monobromcoileinune Codeine
The conversion of thebaine into codeine corroborates the pre
viously (Ber. 1897, p. 1373) expressed opinion of the author that
thebaine, morphine and codeine all have the same constitution and
that the difference in decomposition products obtainable from the
baine on the one hand and morphine and codeine on t he other is due
to the degree of reduction of the phenanthrene complex underlying
the three alkaloids. The opinion is also supported by the observa
tion of Knorr (Ber. 1903, p. 3074) that the enol form of codeinone
having the same type as thebaine really yields the same decomposi
tion products as the latter.
(7"o he continued.)
8N PHA RMA CEUTICAL REVIEW.
By I. W. Brandel.
61. Onion Oil. G.-H.-K., p. 306.

Haensel 77 distilled both the ordinary cooking onions and the
so-called spring onions. The former yielded 0.015 p. c. and the
latter 0.016 p. c. of oil.
The oil from the cooking onions which had the better flavor is
a brown concrete oil, sp. gr. 0.9960 at 35° C. ; m.tp. 23°; aD cal
culated from 5 p. c. ethereal solution = —3° 40'. The oil is com
pletely insoluble in alcohol.
The oil from spring onions is a brownish liquid, sp. gr. at 25° =
0.9725; uD, calculated for 5 p. c. ethereal solution = —1°60'; com
pletely insoluble in alcohol.
OILS OF THE CONVALLARIACE.fE.
62 a. Oil from Convallaria Majalis.
The leaves of Convallaria majalis yield 0.058 percent of a green
volatile oil, which becomes brown. It is solid at ordinary tempera
ture, melting at 40° C., and beginning to boil at 120° C. It has a
pleasant odor, a sharp, spicy taste and an acid reaction. The solid
portion, recrystallized from alcohol forms white scales melting at
61° C.™
OILS OF THE IRIDACEJE.
64, Orris Oil. G.-H.-K., p. 308.
Stead79 obtained orris oil in a fluid state, which has been known
only in a semi-solid state. Five parts of the concrete oil yield one part
of a golden-yellow oil, having a strong odor, which on extreme
dilution produces the odor of violets. The oil has sp. gr. at 15.5°
= 0.9489; «D = —28.25°; congealing point —5°; soluble in 8
volumes of 70 p. c. alcohol. It contains some free acids and also
alcoholic compounds.
" Continued from page 64.
n Hnensel'H Kep., April, 1903, p. 19.
Pharm. Centrulh., 42, 5, 496.
'» Chem. & Drugg., 56, p. 472.
PHARMACEUTICAL REVIEW. Sil
OILS OF THE ZINGIBERACE.E.

67 a. Oil from Kaempferia Galanga.
By distilling the rhizome of Kaempferia gnlanga, L., called Kent-
joer or Tjekoer by the natives of Java, Romlmrgh80 obtained
an oil, the first fractions of which were lighter than water. The
subsequent distillate was heavier than water and congealed to a
crystalline mass, m. p. 50°. The crystals consisted of the ethyl
ester of p-methoxy cinuamic acid :
OCHa
CH = CH.COOC2H5
The liquid portions of the oil contains ethyl cinnamate, a sesquiter
pene, and a hydrocarbon C1sHsa whose properties agree with those
given for pentadecane. More than one-half of the liquid portion of
the oil consist of this para tfin.
69. Oil of Galangal. G.-H.-K., p. 312.
Haensel81 obtained 0.56 p. c. of rectified oil, which had di5° =
0.9135; «D so° = —4.04°; n„2o° = 1.4782; 1 vol. of oil is soluble
in 6 volumes of 80 p. c. alcohol.
Composition. Schindelmeiser8s has isolated d-pinene from
galangal oil. From the fraction of oil boiling 230° to 240° ; aD =
—27° 12', a crystalline dihydrochloride C1sHa4.2HCl, m. p. 51° was
obtained. This compound does not agree with the dihydrochloride
of any known sesquiterpene. Cadinene is also probably present.
Horst8+ has isolated 25 p. c. of eugenol (benzoic ester m. p. 69°
to 70°).
70. Oil from Alpiaia Malaccensis. G.-H. K., p. 313.
According to Komburgh85 the leaves contain an oil consisting
principally of methyl cinnamate. Pinene (nitrosochloride m. p. 108°)
is also present.
72. Ginger Oil. G.-H.-K., p. 313.
Soden and RojahnH0 obtained a new sesquiterpene, zingiherene,
from oil of ginger. It is a thin liquid, resinifying readily. Di5° =
so Koning Akail. v. Wettenxch. te Arost., 1900. p : l'.tO-J, p 618.
»i Hnensel'H Ber.. 1900, (4), p. I 5.
»» Chem. Ztg.. 1>6, p. 808.
s* Pharm. Ztschr. f. Kutwl., 89, p. 378.
ss K. Akad. v. WetenHch. te Amnterdam, 3, p. 451.
»« Pharm. Ztg., 45, p. 414.
!)0 PHARMACEUTICAL REVIEW.
0.872; aD = —69°; I), p. 134° (14 m. m.). From the first runnings
of ginger oil an aldehyde was isolated with sodium bisulphite solu
tion, which was not further identified.
According to Schreiner and Kremers,87 zingiberene has the fol
lowing constants: B. p. 160°—161° (32 m. m.); dao° = 0.8131;
nD = 1.49399; aD — —73.38°. The hydrochloride can be prepared
as follows :
A solution of zingiberene in an equal volume of acetic acid is saturated
with dry hydrochloric acid gas and allowed to stand for two days. White
needles, m. p. 168— 109°, are obtained.
The nitrosite, m. p. 97—98°, is obtained as follows:
Zingiberene is dissolved in ten volumes of petroleum ether and sodium
nitrite and glacial acetic acid added with cooling.
To obtain the nitrosate, m. p. 86°—88° :
Dissolve zingiberene in an equal volume of glacial acetic acid and ethyl
nitrate. Cool and add carefully a cooled mixture of nitric and glacial acetic
acids. Shake out the mixture with cool ether. It is a yellow powder.
The nitrosochloride is obtained as follows:
Dissolve the zingiberene in an equal volume of glacial acetic acid and
ethyl nitrite. Cool and gradually add a solution of hydrochloric acid in
glacial acetic acid. Shake the mixture with alcohol which precipitates the
compound as a white powder, m. p. 96°—97°.
73. Ceylon Cardamom Oil. (i.-H.-K., p. 315.
S. & Co.8S state that Ceylon cardamom oil is no longer distilled
from the fruits of Elettavia cardamomum, var. /3, but from another
speciei. The oil has th/ following constants: Dis° = JO. 9336; «„ =
+ 21* IV; s ipontfic ition tuirnbsr 109; soluble in 3 volumes of 70
p. c. alcohol.
Aicordinj; to Allû and Brewis80 Ceylon wild oil (aD = +12°25';
d =0.9102) has almost the same constants as the Mangalore oil
(«d = +12°30'; il =0.928:i), but there is a very marked difference
in the odor of the two oils.
78. Cameroon Cardamom Oil. G.-H.-K., p. '119.
Cameroon cardamom oil is obtained either from Amomum clusii
or Amomum nngustifolium.90 The fruits yield 1.5 p. c. of oil which
has an odor like oil of bay. di.-,° = 0.9071 ; «„=—23.5°; nD =
1.4075; iodine number 152.1.
»' Pbarm. Arch.. 4. pp. (18. 141, 101 .
ss S. & Co.. Rep.. Oct.. 1901. p. 14.
»» Chem. & MrnKK: 38. p. 48.1.
»o pharm. Cjntralh., l!tol. p. S10: Haensel's Ber., I 1*00, (4>, p. 7.
OILS OF THE PIPERACEÊ.

80. Oil of Black Pepper. G.-H.-K., p. 320.
Schreiner and Kremers91 have identified the sesquiterpene of
pepper oil as caryophyllene (nitrosite m. p. 43°).
83 a. Oil from Piper Famechoni
A new pepper, a native of the French Soudan and U[)per Guinea,
is obtained from Piper famechoni, Heckel. Barille92 obtained from
the fruits, 4.47 p. c. of a very aromatic oil, boiling principally
between 255—260°.
86. Matico Oil. G.-H.-K., p. 325.
Old matico leaves yield 1—3.5 p. c. of a thick, dark colored oil,
having. an odor like cuhebs and mint; sp. gr. 0.93—0.99; dextro
gyrate.
Fresh leaves yield 3—(i p. c. of oil from which asarone separates;
sp. gr. 1.06—1.13; laevogyrate. A sample of oil, sp. gr. 1.123,
examined by Fromm and Ernster93 continued neither matico-campher
nor asarone. 70 p. c. of the oil distilled within 15° and consisted
chiefly of a compound CuHisOi (b. p. 282—285°; di7° = 1.136).
Upon oxidation it yields matico aldehyde m. p. 88° and has the
formula :
CH CH
CH,. M'/\c/0 CH.Oc/X, C/0
CHs0CV^/Cx \y CHgOC
(' II
I I/
CH2 C
! % :
t'H 0
l
L'Hs—(.'—CHs Matico aldehyde.
OILS OF THE CUPULIFERvE.

91a. Oil from Beech Seedlings.
Beech seedlings contain a glucoside and a diastase which gives
rise to the production of methyl salicylate. The glucoside does not
»< Phunn. Arch., 4. p. 61 .
»» Compt. ruirt.. 1H4, p. lr>12.
•a Ber. a."), p. 4a47.
exist in the seed or in old plants but is produced during germina

tion (Tailleur9t).
OILS OF THE MORA.CE.<E.
97. Oil of Hops. G.-H.-K., p. 336.
Chapman93 has determined the mean difference in the specific
gravity of oil of hops for 1° between 15° and 20° C. as 0.00062.
OILS OF THE SANTALACE/E.
99. Sandalwood Oil. G.-H.-K., p. 338.
Properties. According to Potvliet96 genuine unadulterated
East Indian sandalwood oil should satisfy the following requirements :
di5° = 0.975—0.985.
aD — —17° to —20°.
Soluble in 4—4.5 vol. of 70 p. c. alcohol at 20°.
Santalol content at least 92.5 p. c.
It is quite possible to prepare mixtures of East Indian sandal
wood oil with West Indian and cedarwood oils which meet the
ordinary requirements.
Compositions. (iuerbet97 has corrected the specific gravity
of the oil on which his investigation was made and which made
his results unreliable. 08 The sp. gr. should have been 0.9871 at 0"
instead of 0.9084. 1,9 Guerbet has obtained crystalline nitroso-
chlorides and corresponding piperidides of the two sesquiterpenes.
The a-santalene yiejds a nitrosochloride melting at 122° and a
piperidide melting at 108—109°.
/8-santalene gives two isomeric nitrosochlorides, m. p. 106° and
and 152°; the piperidides melt at 104° and 101°.
The two santalols to which Guerbet still attributes the formula
C15H26O have the following constants and are primary alcohols:
a-Santalol : b. p. 162°—163° (13 m. m.) ; 300°—301° (760 m. m.) ;
d(,° = 0.9854; «„ = —1.20°.
/8-Snntalol: b. p. 170°-171° (14 1n. m.); 3093-310° (760 m.m.);
do° - -- 0.9869; «„ =: —56°.
a-Santalol yields an acetate by boiling with acetic acid anhydride
which boils at 308°—310°. The /3-santalol acetate boils at 316—317°
»* Compt. rend., 182. p. 1235.
•« Pharm. Kev., 21. p 155.
»« S. & Co., Kep.. Oct. 1901, p. 48.
»' Bull. Soc. Chim.. Ill, 2a, pp. 540. 542.
»» O.-H. K., p. 842.
»« Compt. reml., 1a0, p. 417.
PHARMACEUTICAL REVIEW. IK!
According to Soden,1 o-santalol is slightly dextrogyrate, +1°40

to + 2° 4' and yields an acetate boiling at all—312°; dis°=0.988;
«d = +3°. He gives C15H24O as the formula for santalol.
Mueller2 has examined the non-alcoholic part of sandalwood oil.
A hydrocarbon, C9H14, called santene was isolated; b. p. 139—140°;
dis° = 0.8710. It yields a nitrosochloride in two modifications:
a-nitrosochloride is blue and melts at 108° and gradually changes
to the white /{-compound, which when heated changes back to the
blue compound at 1)0°. Santene hydrochloride melts at 86°; tribro-
mide m. p. 62°.
By treating the low boiling fractions of the oil with semicar-
bazide, two semicarbazones, melting at 175° and 224° are obtained.
The first compound when decomposed with sulphuric acid yields a
ketone, C1iH160, santalone, which boils at 214—215°; di5° = 0.9906;
aD = —<>2°. Its oxime melts at 75°.
The original oil contains 0.5 p. c. of teresantalic acid, C10H14O2,
m. p. 157°. It yields a dihydrochloride m. p. 185° from which a
lactone of teresantalic acid can be produced which has an odor like
borneol, m. p. 10:3°. By boiling the acid with sulphuric acid a-san-
tene is obtained.
Upon oxidizing oil of sandalwood with potassium permanganate,
Chapman,3 obtained a crystallene compound, C13H20O2, which he
called santalenic acid. It melted at 76°; b. p. 189° (28 m. m.) and
can be distilled with steam. aB from alcohol solution +18.05°.
Oil of sandalwood is official in the following pharmacopoeias:
GERMAN BULGIAN DUTCH SWEDISH
4th ed. 1903 ed. 1908 ed. 8th ed.
Color pale yellow light yellow yellow
Sp.gr. atl5c 0.975—O.S)85 0.975—0.985 0.975-0.990 0.970—0.985
aD slightly laevot
Solubility .... 5 vol. dil. ale.2 5 vol. 70 p. c. 5 vol. dil. ale. 5—0 vol. of ale.
alcohol (1 vol. alcohol,
4 vol. dil. ale.)
Santalol 90 p. c. 90 p. c.s 90 p. c.
Boiling pt... 300° 295—295°
t May be up to —20°. S. & Co.
> Good oils wUl not pass this test. Potvllet.
a Calculated on formula CisHjgO, which IB equal to 89.20 p. e.
calculated from CisHaiO. S. & Co.
i Arch. d. Pharm., 238, p. 853.
a Arch. d. Pharm.
• Journ. Chem. Soc., 79, p. 1B4.
OILS OF THE ARISTOLOCHIACEJE.

105. Oil of Canada Snake-root. G.-H.-K., p. JJ47..
Power and Lees* have further examined snake-root oil. The oil
examined had sp. gr. = 0.9.">2; «0 = —3° 24'. It contains a phenol,
C0H12Oa, having an odor somewhat like creosote; palmitic acid,
m. p. 00—61°; d-pinene (nitrosochloride, m. p. 103°; nitrolpiperidide,
m. p. 118°); d-linalool (a-citryl-/J naphthacinchoninic acid, m. p.
195—198°). The substance previously called asarol5 is undoubtedly
d-linalool. 1-borneol (campheroxime, 111. p. 115°); 1-terpineol (dipen-
tene dihydriodide, m. p. 80°); geraniol (phenylurethane, m. p. 82°);
eugenol methyl ether, 36.9 p. <•. (bromoeugenol methyl ether dibro-
mide, m. p. 79°); a lactone, C1 + H20O2, acetic acid and a blue oil of
an alcoholic nature.
105 a. Oil from Asarum Arifolium.

From the leaves and roots of Asnrum arifolium Miller0 obtained
7 to" 7.5 p. c. of oil with a pleasant aromatic odor like sassafras.
Three samples of oil had the following constants:
I. 11. in.
Sp. gr 1.0585 1.0609 1.0613
an —3° —2° 55' -3° 7'
uD20° 1.531875 1.531460 1.531065
The oil contains safrol (a-homopiperonylic acid, m. p. 128°);
1-pinene (nitrosochloride, m. p. 103°); eugenol (benzoyl compound,
m. p. 69°); and a small quantity of another unidentified phenol;
methyl eugenol (tribromide, m. p. 7H°); methyl isoeugenol (dibro-
mide, m. p. 99°—101°); asarone, m. p. 62°—63°.
OILS OF THE POLYGONACEAE.

107 a. Oil from Polygonum Persicarla.
The herb of Polygonum persicariu, L., used in Russia as a popu
lar remedy, contains 0.05!1 p. c. of oil. According to Horst7 the
bulk of the oil consists of volatile fatty acids, of which acetic and
butyric acids were isolated in the form of their silver salts. The oil
also contained a crystalline camphor-like substance, called persicariol.
* Joum. Chem. Soc.. 81. p. 59.
« G.-H.-K., p. H+H.
« Arch. d. Pharm., 240. i>. 371.
i Chem. Ztg., 25, p. 1055.
PllA KMACEVTICAL REVIEW.
OILS OF THE CHENOPODIACEAE.

108 a. Oil from Camphoroama Monspeliaca.
Cassan8 obtained 0.2 p. c. of oil from Cmaphorosma monspeliaca,
a shrub growing in southern France. The oil had a greenish-yellow
color, an odor like bitter almonds, <1it° = 0.970; nDi5°= 1.3724.
The oil congealed at +4° C.
OILS OF THE RANUNCULACEAE.

111. Nigella Oil from Nigella Damascene. G.-H.-K., p. 352.
According to Haensel 9 the seeds of Nigella dnmascena yield 0.256
p. c. of an oil with the following constants: sp. gr. at 15° = 0.9072;
«D = —7.8° ; nD 20° = 1.5582.
Aubert™ gives d.2->° = 0.9093; nn2*° = 1.494: insoluble in 23
volumes of 80 p. c. alcohol.
Pommerelme 11 has determined the formula of damascenine, to
which the blue fluorescence is due, as C9H11NO3, m. p. 26°. Damas
cenine contains one methoxyl group and when boiled with alcoholic
potash solution, forms crystals melting at 76—77°. The potash
probably converts the compound into an amido acid.
OILS OF THE MAGNOLIACEAE.

114a. Star Anise Oil. G.-H.-K., p. 353.
According to S. & Co.12 star anise oil sometimes has a slight
dextro rotation, but is usually laevo rotatory. The constants of
such an oil are: dm° = 0.9893; an=+0°18'; congealing point
+18°; soluble in 2 volumes of 90 p. c. alcohol.
Tardy18 has examined oil of star anise from which the greater
part of the anethol had been removed. The oil had «D = —3.15°.
In addition to the already identified compounds, d-pinene, 1-phel-
landrene, methyl chavicol, hydroquinone ethyl ether, anisic aldehyde
and anisic acid, the oil was also found to contain anisic ketone
C10H12O2 (p-methoxyphenylacetone oxime, m. p. 72°) ; a l-sesquiter-
pene; a compound C20H22Oa, m. p. 212°, and possibly a d-terpineol.
b Thesis, Montpelller, 1901.
» Haensel's Iier.. 1901, 11. p. 21!.
t0 Journ. Am. Chem. Soc., 24, pp. 091, 778.
t1 Arch. d. Pharm.. 2!I«. p. 546: 289, p. 84.
"
i» 8. & Co.,
Soc. Kep.,
Chiro.,Oct.
Ill,1903,
27, p.p. 990.
64.
Bull.
116. Japanese Star Anise Oil. G.-H.-K., p. 362.

Tardy11 has examined the oil obtained from the dried fruit of
niicium religiosum by extraction with petroleum ether. The oil had
aD — —1°50'. The oil contains eugenol, cineol, safrol (piperonylic
acid, m. p. 228°); anisic acid; a hydrocarbon yielding a dihydro-
chloride, m. p. 49° and one yielding a monohydrochloride, m. p.
125°.
OILS OF THE ANONACEAE.
118, 119. Ylang-Ylang Oil and Cananga Oil.
G.-H.-K., p. 362.
Prepara tion. The ylang-ylang tree is propagated by planting
seedlings or cuttings about 20 feet apart each way, when they grow
rapidly in almost any soil. The first flowers appear in the third
and in the eighth year. A tree yields as high as 100 lbs., the blossoms
growing in every month of the year. About 75 lbs. of flowers yield
1 lb. of oil. is
Composition. S. & Co.16 have identified isoeugenol in ylang.
ylang oil. It yielded acetyl eugenol, m. p. 101°—102°. The oil also
contains benzoic and salicylic acids which are in the oil in the form
of esters of methyl and benzyl alcohols.
From cananga oil a terpene (nitrol benzylamine, m. p. 123°)
was isolated. B. p. 160°; «„ - +16° 20', and a ketone of a peculiar
odor boiling 145—143°.
By distilling the aqueous liquor resulting from the saponification
of ylang-ylang oil, Darzens17 identified methyl alcohol. The phenols
contained p-cresol (benzoyl compound, m. p. 70—71°). The p-cresol
is probably present in the oil as acetyl-p-cresol which compound has
a ylang-like odor.
119 a. Oil from Xylopia Ethiopica.
The fruits of Xylopia ethiopica, called Ethiopian pepper, contain
a fragrant volatile oil, which was not examined. 18
i* Bull. Soc. Chim., IIT. 27, p. 987.
is Chem. & Drugg., 1902, p. .
J« S. & Co., Rep., Oct.. 1901, p. 58.
« Bull. Soc. (,'him., Ill, 27, p. 88.
is Pharm. Ztg.. 40, p. 092.
Volume 26. APRIL, 1908. Number 4.
Hematoxylin as an Indicator in the Titration of

Phosphoric Acid.
1{y A. li. Lyons.
In the complete neutralization of phosphoric acid by an alkaline

hydroxide there are three successive stages, corresponding with the
formation of phosphates containing in each molecule respectively
one, two and three atoms of the alkali metal. By the use of different
indicators, as is well known, these stages may be demonstrated.
The completion of the first reaction, resulting in the formation of a
di-acid phosphate (e. g. KH2PO4), is signalized by indicators such
as methyl orange, which are sensitive to feeble alkalies. Such are
cochineal and iodeosine. either of which may be used in the titration
of phosphoric acid.
The change of color, however, invariably occurs in a dilute solu
tion before the theoretical quantity of alkali has been added, so that
the result of a titration, when one of these indicators is used, is lower
than it should be, unless the volumetric solution has been standard
ized against a phosphoric acid solution of known strength. Even
then, it is essential that the acid be brought always to approxim
ately the same strength as that used in standardizing the volumetric
alkali. It is necessary also to avoid disturbing foctors such as the
presence of various salts which may determine a different ionization
of the phosphates present.
Indicators sensitive to acids rather than alkalies do not show
any change of color at that stuge of the titration. When, however,
two of the hydrogen atoms of the acid have been replaced by the
alkali metal, they proclaim that the acid is fully saturated or
neutralized, yet generally in a somewhat hesitating way, the charac
teristic color change taking place gradually. It is an indicator of
this class which has been commonly chosen for acidimetric deter
mination of phosphoric acid, viz. phenol-phthalein.
(97)
9H PHARMACEUTICAL REVIEW.
As alkali is added, there comes a point where a faint pink color,

persisting after the mixture is stirred or shaken, makes its apperance.
Another drop of the reagent deepens the color, but several more are
required to bring out the red we are looking for. The true end point
is therefore not easy to determine. A sharper change takes place in
presence of a salt like sodium chloride, and the U. 8. P. prescribes
such addition. As a matter of fact, the quantity of chloride added,
as well as the degree of dilution of the acid, influences the reaction
which the indicator makes visible, so that correct results can be
reached only by adhering strictly to a routine in which the details
are prescribed, so as to insure identity in the conditions.
It is easy to demonstrate both critical points in the reaction by
the use of two indicators added simultaneously, e. g. methyl orange
and phenol-phthalein. All this is an old story, but there is another
chapter to it, which is not so familiar. Suppose that, after the red
color has appeared, announcing that the acid has been two thirds
neutralized, a neutral solution of barium chloride be added; instantly
the red color disappears, and alkali may now be added, theoretically,
until the acid is completely neutralized, before the solution will again
become red. As a matter of fact, the color change again anticipates
the completion of the reaction, so that the true end point cannot
be determined directly. It is necessary to add a slight excess of
alkali — the quantity being already approximately known by the
changes of color at the end of the first and again of the second
stage. If the solution is sufficiently dilute the precipitated barium
phosphate will quickly subside so that the greater portion of the
fluid can be decanted clear and titrated back with volumetric hydro,
chloric acid. It is possible thus theoretically to determine quite
accurately the end point of the third stage, and results thus ob
tained, provided a fixed mode of procedure be adhered to, are
reasonably self consistent, and sufficiently near the truth to be of
practical value. I find that they are always a little high, as might
be expected on theoretical grounds.
The following routine may be suggested. Use in the first place
a volumetric alkali (deci-normal) which contains a little barium
chloride, to ensure absence of carbonate. Dilute the acid to be
titrated so that it shall contain about one per cent, of phosphoric
acid. Of this, use 10 cc. Add a few drops of phenol-phthalein T. S.
and run in slowly from a burette volumetric alkali until a distinet
PHA KMACE UriCA L RE VIEW. 99
red color (permanent) is produced. Note the amount of alkali re

quired and add one half as much more. Then add slowly 5 cc. of a
strictly neutral ten per cent, solution of barium chloride, with con
stant shaking. Finally add 3 cc. more of volumetric alkali (i. e. one
tenth the total quantity already added) and record the reading of
the burette. Shake the mixture that has been titrated, which should
be contained in an Erlenmeyer flask, during one minute, then allow
the precipitate of barium phosphate to subside. Decant the clear
fluid as closely as practicable from the precipitate — it is not essential
that it be absolutely free from turbidity — and titrate back with
deci-normal hydrochloric acid. If necessary, calculate from the
volume of the residual portion of fluid the amount of acid that
would be required to neutralize it, and add this to the amount of
volumetric acid consumed in the titration. Finally subtract the
total acid from the volumetric alkali, and multiply the remainder
by the factor 0.003243 to find the quantity of phosphoric acid
(HaPO*)in the solution titrated.
On the same principle lime water may be employed for the titra
tion, in place of a volumetric alkali. The titre of the lime water
against deci-normal hydrochloric acid must first be accurately deter
mined. If the lime water is of full strength, 100 cc. of it will require
more than 40 cc. of the acid. By a preliminary experiment ascertain
how much of the lime water is required to produce apparent incipient
alkalinity in 10 cc. of the (approximately one per cent.) phosphoric
acid, cochineal being used as indicator; multiply this amount by 3.5,
and measure into a small flask that exact quantity of the lime water
— not far from 140 cc. probably. To this add slowly with constant
shaking exactly 10 cc. of the diluted phosphoric acid. Add phenol-
phthalein indicator, and distilled water (of assured neutrality, and
free from carbon dioxide) to make up 200 cc. Cork the flask securely
and let it stand at rest until the precipitated calcium phosphate has
well subsided. Then take off with a pipette 50 or 100 cc. of the
clear fluid and titrate back with deci-normal hydrochloric acid. An
alternative procedure, when an immediate result is required, is to
filter the liquid containing the precipitate through a filter free from
acid or alkali, rejecting the first 50 cc. of filtrate, and then collecting
for titration 100 cc., or other convenient aliquot part. In any case,
of course the operation must be conducted rapidly, with precautions
against the absorption of carbon dioxide. The results are fairly
near the truth, at least when the excess of lime water is not greater
than 10 cc.
An indicator of alkalinity lauded by some but not in favor with
most chemists, is hematoxylin. Its idiosyncrasies are well illustrated
by its behavior towards phosphoric acid during the course of its
neutralization with an alkaline hydroxide. Other indicators are
content to answer yes or no to definite questions as to the presence
of hydrogen or hydroxyl ions. Hematoxylin is of a Ilooseveltiau
temper, always having something to say about existing conditions,
and saying it with emphasis. Its language has not been fully
learned, but it certainly has a rich vocabulary. When a freshly
prepared solution of hematoxylin is added to a sample of diluted
phosphoric acid, and a volumetric alkaline solution is slowly added,
no change is at first produced, except that each drop of the alkali
develops a purple color at the point of contact, giving place to a
more or less pronounced yellow color in the fluid as it disappears.
The yellow is much stronger if the hematoxylin solution is allowed
to stand even a short time exposed to the air. At a certain point,
corresponding with the end of the first stage of neutralization, there
is a sudden change from yellow to pink or lavender, the particular
shades of yellow and lavender varying greatly according to the age
and the strength of the indicator solution, but the change always
occuring sharply, except in presence of interfering salts such as
sodium chloride. If sodium chloride is present, the change is deferred
and is not sharp. In a particular titration, this first permanent
change occured after adding 3.10 cc. of deci-normal alkali. In
presence of sodium chloride it would not occur until 3.30 cc. or
more had been added. Addition of more alkali causes a rapid pro
gressive change so that at 3.5 cc. the color is a strong amethyst-
purple, passing then to a purplish-blue or deep violet at 4.0 cc.
From this point the color does not change greatly until 5.0 to 5.5 cc.
have been added, when there begins to be a return to an amethystine
hue, in which red more and more predominates until the color be
comes a raspberry-red. It is noticed at this time that each drop of
alkali added produces locally a brick-red color, and at about 6.3 cc.
there comes a sudden change — if the drops do not follow one an
other too fast — the fluid assuming a peculiar smoky brown color.
This point is important, for it marks with considerable exactness
the end of the second stage. The next drops of alkali change the
color to a clear brown, the tint much paler than any of those that
immediately precede or follow. By the time 6.85 cc. have been added,
a change begins which passes on to the development of a garnet
color, which shades later towards amethyst. The changes are

gradual until almost 8.50 cc. alkali have been added, when the color
deepens until it resembles that of a solution of permanganate. The
color then does not noticeably change on further addition of the
reagent. This final color change should mark the end of the third
stage of neutralization ; in fact it occurs much too early. In the
above titration the three critical points should have been respectively
at 3.18, 6.35 and 9.53; as observed they were at 3.10, about 6.3
and 8.8 to 9.0.
It is now evident why hematoxylin is not suitable for use as a
general indicator. The color changes it exhibits no doubt have each
a definite significance, but we comprehend as yet the meaning of
only a few of these changes, ami even these few we are not sure that
we understand except under certain prescribed conditions. It does
seem possible, however, to put some confidence in what it has to
say about the neutrality of phosphate solutions, in absence of
.disturbing molecules or ions. The first color change is one of great
sharpness, so that if our alkaline solution has been standardized
against phosphoric acid of known strength, and acid solutions of
nearly uniform strength are employed, we may expect results of a
high degree of exactness. The second color change seems to be little
affected by the presence of sodium chloride, and it occurs quite close
to the theoretical point, so that we may place a good deal of con-
fidence in results depending upon it. Unfortunately the change is
not as sharp as could be desired, so that no great degree of exact
ness can be secured in the result, unless it shall be found that the
addition of some supplemental color will give greater definiteness to
the end point.
There is here opportunity for experimental research. The added
color must be one which so modifies one of the two colors as to in
crease the contrast between them, as addition of a green in case of
methyl orange indicator, green being complimentary to red and so
darkening greatly the color of the acid solution, while having com
paratively little influence in modifying the yellow indicative of
alkalinity. I found it an interesting experiment to add to the acid
a little methyl orange together with the hematoxylin. The results
were quite surprising, but need not be detailed here. They showed
simply that hematoxylin color changes are subject to most profound
modifications from trivial causes. Meanwhile there is a satisfaction
in finding one use to which the erratic indicator hematoxylin may
be put.
The Isoterpenes of Flawitzky.
By Edward Kremein.
Possibly no chapter of organic chemistry has suffered more from

a confusion of names and synonyms than has the one commonly
comprised under the designation of terpenes and camphors. Whereas
much of the misunderstanding has been cleared up during the past
twenty years, sufficient remains to annoy the investigator.
Though one would scarcely expect that the isoterpenes of Fla
witzky could have contributed to this condition, they do not appear
to have found their place in the fairly well regulated classification
of these compounds at the present time. Thus, e. g. Heusler and
Pond,1 although they enumerate the term isoterebentene among the
synonyms for dipentene, do not mention the isoterpenes, either in
the chapter on limonene or in the index. An oversight would seem
out of the question in this case. The only explanation that seems
plausible is this, that the authors did not regard the "Terpen
Hydrate" and the "Isoterpene'" of Flawitzky as sufficiently
characterized to place them beyond reasonable doubt. Such being
the case, the following communication may not be totally out of
place at this late date.
Flawitzky began his investigations along this line in 1879 2 on
the laevogyrate modifications, and concluded them in 1885 s on the
dextogyrate modifications. The changes brought about are briefly
as follows : Dextropinene obtained from Russian oil of turpentine,
and laevo pinene from French oil of turpentine were hydrated by
means of dilute alcoholic sulphuric acid. The hydrates were
dehydrated by means of acetic acid anhydride. Leaving out of
consideration the byproducts which he obtained, a survey of his
results can readily be had by a glance at the physical constants of
his products. These constants are herewith tabulated.
i The Terpenes.
a Berichte, 12, pp. 1400 and 2H."4.
a Ibid.. 20, p. 1956.
"Rectitea Terpen." "Linkea Terpen."

Wd + 32.0° -43.4°
b. p. 155.5°—156.5° 155°
d°4 0.8764 0.8749
0.8600 0.8587
"Rechtea Terpen Hydrat." "Linkea Terpen Hydrat."
M„ + 48.4° -56.2°
b. P. 213.7°-217.7° 217.7°—220.7°
d°4 0.9335 0.9340
"Rechtea Isoterpen." "Linkea Iaoterpen."
[«]„ + 57.6° —61.0°
b. p. 178.3° 179.3°
d°4 0.8627 0.8639
dW 0.8480 0.8486
At the close of his first article, Flawitzky points to the close

relationship between his "Linkes Isoterpen" and the hydrocarbon —
now known as 1-limonene — from elemi oil. He further states that
he expects the "Rechtes Terpen" to yield a corresponding "Rechtes
Isoterpen" which ought to bear a simitar relation to the terpene —
now known as d-limonene — from lemon oil.*
He concludes the considerations of his second article with the
following statement: "Nach diesen Erwilgungen kijnnen die von mir
durch Isomerirung der Terpene dargestellten Isoterpene von den
natiirlichen Isoterpenen sich allein nur durch grosseren oder geringe-
ren Gehalt an inactiven Isoterpenen unterscheiden.5
Unfortunately for the positive chemical identification of the
artificial isoterpenes with the "natural isoterpenes," the nitroso
chloride reaction had not yet been perfected. Flawitzky was de
pendent, therefore, on the d Hydrochloride of the "isoterpenes"
i. e. dipentene dihydrochloride; while he recognized with Berthelot
that his "terpene" (pinene) could yield this compound under proper
conditions as well as his isoterpene (limonene).
In 1891 I pointed out that the isoterpenes of Flawitzky were
evidently "more or less impure limonenes."8 Two years later I had
occasion to have Fhiwitzky's work repeated — the dehydration with
slight modification — and to supply positive chemical proof of the
« Rerlchte, 12, p. 2358.
• Ibid., 20, p. 19«S.
• The limonene group of terpenes, Traux. Wis. Acad. Sc., Arts and Letters, *.
p. 840.
conversion of optically active pinene to an optically active limonene

through a corresponding terpineol. The work on the laevogyrate
modifications was done by Mr, M. H. Strehlow; that on the dextro
gyrate modifications by Mr. E. Williams in fulfilment of the thesis
requirement for the degree of Graduate in Pharmacy, class of 1893.
The French oil of turpentine had a specific gravity of 0.8777
and in a 100 mm. tube turned the plane of polarized light 30.116°
to the left, hence [a]D = —:(4.31°. The corresponding constants of
rectified American turpentine oil were 0.8635 and [«]D — +12.8°
respectively.
The hydration was affected as directed by Flawitzky and the
hydra ted oils were fractionated with the following results:
Hydration products of
French turpentine oil. Am. turpentine oil.
Fractions. Sp. Or. at 20° [«].i Sp. Gr. at 20° Fractions.

• + 11.0° 0.883 165-170°
. + 8.8° 0.80!) 170—175°
175-180° 0.8826 -37.06° + 0.5° 0.901 175-180°
180—185° 0.8736 —36.87° + 5.9° 0.885 180-185°
185—190° 0.8944 —33.68° + 4.9° 0.883 185—190°
190—195° 0.8870 —33.26° + 5.0° 0.904 190—195°
195-200° 0.8934 —33.14° + 4 9° 0.907 195—200°
200—205° 0.9083 —35.68° + 5.2° 0.918 200—205°
205—210° 0.9090 —42.22° + 5.6° 0.920 205—210°
210—215° 0.9140 —49.43° + 6.0° 0.922 210-212°
215-220° + 6.8° 0.925 212—214°
+ 6.8° 0.925 214-216°
+ 7.5° 0.927 216-218°
Both the initial hydrocarbons and the hydration products show

lower angles of rotation than the corresponding products of Fla
witzky. Whereas, the higher boiling hydration products from the
French oil show a higher angle of rotation, those from the American
oil show a lower angle of rotation.
As dehydrating agent Flawitzky employed acetic acid anhydride.
He, however, obtained an unstable acetate as byproduct which
decomposed upon fractionation. In order to avoid these byproducts
potassium acid sulphate, which Wallach had found admirably suited
for this purpose, was used. For each part of hydrated oil, two
parts of potassium acid sulphate were token and the mixture heated
to about 180° for about eight hours. The dehydration product was
distilled with water vapor, the distilled oil dried and fractionated.
Of the laevogyrate products fractions 210—215° and 215—220°
were thus dehydrated, of the dextrogyrate products fractions 205
to 210°, 210—212°, 212—214° and 214-216°. The results are
herewith tabulated :
Laevogyrate Dehydration Products
Of fractions 210—21S". Of fractions 215—220J.

Sp. Gr. at 12°. [«]n Fractions. Sp. Or. at 20° [«]o__
0.8640 -39.51° 175-180° 0.8640 -39.51°
0.8699 —•17.21° 180—185° 08699 -37.21°
0.8940 —34.85° 185—190° 0.8940 -34.83°
0.9060 —39.16° 190—195° 0.11060 —39.10°
Dextrogyrate Dehydration Products

Of fraction 2OB—210J.
Fraction. Sp. Gr. ut 20°.

173—176° 0.938 +0.42°
170—180° 0.885 +0.47°
180—185° 0.917 +0.47°
Of fraction Of fraction Of fraction
210—212°. 212- 21*°. 214— 216°.
Fraction. Hp. Or at Sp. Or. at [«]n Sp. Or. at
20°. M„ 20°. 20°. Md
175-180° 0.852 +1.70° 0.859 + 1.2°

180—185° 0.914 +4.2° 0.861 + 1.50° 0.873 + 1.6°
185—190° 0.905 +4.3° .
190-195 0.903 +4.0° ■
Identification of Laevogyrate Dehydration Products.

Fraction 175—180° of the first series (from hydrate 210—215°)
yielded a nitrosochloride only partly soluble in twice its weight of
ether. The crystals resulting from the ethereal solution had two
distinct forms: the one kind was needle-shaped, the other in plates.
The melting point of these crystals was found to be 74—70°, whereas
the melting point of the nitrosochloride insoluble in ether was

100-102°.
The higher fractions of this series yielded but small amounts of
nitrosochloride, too small for further work.
Fractions 175—180° of the second series (from hydrate 215 to
220°) yielded a nitrosochloride only partly soluble in twice its
weight of ether. The ethereal solution yielded, upon evaporation,
needle-shaped crystals resembling dipentene a-nitrosochloride. Crys
tals resembling the a-compound of limonene nitrosochloride could
not be detected. The benzylamine base, recrystallized from alcohol,
yielded prisms melting at 98—100°. The limonene compound melts
at 92—93°, the dipentene compound at 109—1 10°.
This fraction also yielded a crystalline bromide, resembling
dipentene tetrabromide, which after recrystallization from acetic
ether melted at 124—125° thus identifying it as such.
Identification of Dextrogyrate Dehydration Products.
From fraction 180—185° of the second series from hydrate 210
to 212°, a small amount of nitrosochloride was obtained.
From fraction 175—180° of the fourth series (from hydrate 214
to 216°) a small amount of nitrosochloride was obtained. When
treated with twice its weight of ether but a small amount went into
solution. The residue was dissolved in chloroform and precipitated
with methyl alcohol in the form of woolly crystals melting at 103°.
The nitrolbenzylamine base melted at 98—100°.
From fraction 180—185° of this series a bromide was obtained
which after recrystallization from acetic ether melted at 123—124°,
thus identifying it with dipentene tetrabromide.
Attempts to make nitrosochlorides or tetrabromides from some
of the fractions of the other series of dehydration products gave
negative results.
Conclusion. Flawitzky's conclusion, based on a comparison of
physical properties, that his isoterpenes are identical with those
hydrocarbons now generally designated limonene is thus verified
chemically. His suspicion that a considerable amount of what we
now designate dipentene is formed is herewith also established
chemically.
Progress in Alkaloidal Chemistry during the Year 1906*
By H. it, Gordin.
The hydrobromide of bromcodeinone can be made by one of the

following methods. 1. A solution of bromine in chloroform is added
drop by drop to an ice cold solution of thebaine in the same solvent
and the chloroform sucked off in a desiccator. On dissolving the
brown viscous residue in hot alcohol only a small amount of crystals
separate out on cooling. 2. Instead of removing the chloroform it
is shaken with dilute hydrobromic acid for about half an hour and
the crystals which separate out recrystallized from very dilute
alcohol. 3) A solution of bromine in glacial acetic acid is added
to a cold solution of thebaine in the same solvent and the crystals
which separate out on standing are recrystallized from very dilute
alcohol.
The hydrobromide has a yellowish-brown color and corresponds
to the formula, C1sHisBrNOa.HBr + H2O. The water cannot be
removed by heating the salt to 130° in a current of hydrogen. The
free brominated base is precipitated from the hydrobromide by
ammonia, alkalies or alkaline carbonates. The monobromcodeinone
is insoluble in excess of alkali. On prolonged boiling with alkali it
goes into solution with partial decomposition. When heated for a
few minutes with hydrochloric or hydrobromic acid most of the
bromcodeinone crystallizes out unchanged.
The hydrochloride of bromcodeinone separates out in needles
when bromcodeinone is dissolved in hot dilute hydrochloric acid.
Dried at 100° the salt has the formula, C1sHisBrNOs.HCl + 2H20.
One molecule of water can be driven-off at 150° leaving a compound
in which the second molecule of water must belong to the constitu
tion of the salt.
The free bromcodeinone was obtained in crystalline form by
adding ammonia to a solution of bromcodeinone hydrobromide in
dilute alcohol. It is insoluble in water, difficultly soluble in ether
but easily soluble in chloroform. It does not react with methyl
iodide to form an addition compound but when heated with methyl

iodide to 100° is converted into the hydriodide of bromcodeinone.
As, according to Ach and Knorr (Ber. 1903, 3073) oodeinone easily
combines with methyl iodide, the stability of bromcodeinone towards
this reagent must be ascribed to the influence of the bromine atom
upon the nitrogen atom.
The oxime of oxycodeinone, C1sH"i8(0H)(: N.OH), was obtained
by boiling the hydrobromide of bromcodeinone with hydroxylamine
hydrochloride till the hydrobromide did not separate out any more
on cooling the liquid. After setting the oxime free it was shaken
out with ether. The oxime is soluble in dilute alkali.
The conversion of bromcodeinone into codeinone was accomplished
by digesting the hydrobromide of bromcodeinone with iron filings
in presence of dilute sulphuric acid in the cold until the salt went into
solution. The filtered liquid was then made alkaline with sodium
carbonate and shaken out with chloroform. The codeinone was
identified by the melting point of its oxime. (Ber. 1906, 844.)
L. Knorr and H. Hi'irlein have succeeded in converting thebaine
into codeinone and codeine. It had been shown by Ach and Knorr
(Ber. 1903, 3067) . that potassium permanganate or chromic acid
oxidizes codeine to codeinone which by reduction can be reconverted
into codeine. This codeinone occupies an intermediate position
between codeine and thebaine.
CisHmNOs CisHieNOa CsH^NOs
Codeine Codeinone Thebaine
According to Knorr (Ber. 1903, 3074) thebaine is the methyl ether
of the enol form of codeinone and the relation between morphine'
codeine, codeinone and thebaine can be expressed by the following
scheme in which the arrows indicate the transformations so far
accomplished :
% -O.CHs ^ -O.CHa
—CH.OH > CisHuNO V-CH.OH < > (',-,11,, NO >—0 = 0
—CH;. J —CH2 ) —CHs
.Morphine Codeine Codeinone
\ -O.CHs
CsHuNO V-C.O.CH...... (in 0)
) -cm
Thelmlne
rHA RMA CEUTICAL REVIEW. 109
The methoxyl group of thebaine situated in (6) of the

phenanthrene nucleus is so easily saponified that in the transforma
tion products in the preparation of which acids are used the CH3O
group is replaced by an OH group. In the transformation of the
baine into thebenine, for example, the saponification of the CH3O
group is effected even by dilute acids in the cold upon standing or
by a few minutes' boiling with dilute hydrochioric acid. As phenol
ethers are generally not easily saponittable the easy saponification
of the CH3O in (6) of thebaine must be ascribed to the presence of
the double binding next to the carbon atom to which the CH3O
group is attached. All such derivatives of vinyl alcohol are easily
changed into an alcohol and an aldehyde or a ketone
CRnia -CRg O.Alkyl + HaO- CHR1R2— CRs = 0 + Alkyl.OH
(As all such derivatives of vinyl alcohol can be looked upon as
ethers of the enol form of aldehydes or ketones the authors pro
pose to call such ethers enol ethers). In the conversion of thebaine
into thebenine or morphothebaine the thebaine is most probably
first converted into the ketone codeinone according to above equa
tion. While this supposition is supported by the fact that codeinone,
like thebaine itself, can be converted into thebenine, morphothebaine
or thebainone (Ber. 1905, 15160 and 3170) it is only now that the
authors have succeeded in directly converting thebaine into codeinone.
Attempts to reconvert codeinone into thebaine by passing through
the ortho ether of codeinone
0.CH3
,, O.CHs
I O.CH3
UHa
which ought to be obtained by the action of ortho formic ester on
codeinone were not successful.
The conversion of thebaine into codeinone was carried out by two
methods:
1. Boiling with normal sulphuric acid. On boiling thebaine with
normal sulphuric acid for t>—7 minutes, and shaking out the cooled
liquid, after making it strongly alkaline, with ether codeinone was
obtained in crystalline form. Thus obtained the codeinone is con
taminated with thebaine which is shown by the red color of its so
lution in concentrated sulphuric acid. For purification the codeinone
was converted into its oxime, the latter dissolved in sodium hydro
xide, the alkali saturated with carbon dioxide and the precipitated
oxime recrystallized from alcohol.
2. The same codeinone can be obtained by digesting thebaine
for 17 days with cold normal sulphuric acid and working up the
product in the same way as in 1.
In both methods considerable codeinone is lost by the action of
the acid which converts it into thebenine and other products.
(Ber. 1906, 1409.)
It. Pschorr and W. Haas find that when thebaine is treated with
benzoyl chloride the products are similar to those which are obtained
by the action of acetic anhydride on a-methylmorphimethine or upon
thebaine, namely, derivatives of thebaol and of ethanohnethylamine
/\
THs.O/ » \
I» i|
l«
HO\
HOX'Ho.CH2.NHCCHs)
/ Ethunolmethylamine
|5
la
CHa.0\
Thebaol
The benzol thebaol was prepared by digesting thebaine with
benzoyl chloride, mixing the reaction product with ether and remov
ing the unchanged thebaine as hydrochloride with water. The excess
of benzoyl chloride was removed from the ethereal solution either
by shaking with dilute sodium hydroxide or by boiling with methyl
alcohol and distilling off the methyl lwnzoate in vacuum. The residue
of the ethereal extract containing the benzoyl thebaol was recrystall
ized from glacial acetic acid. A dibromide of this benzoylthebaol
was made by treating the benzoyl compound with bromine in chlo-
roformic solution, evaporating the solvent and, after boiling the
residue with alcohol, recrystallizing it from glacial acetic acid.
When the benzoylthebaol is oxidized with chromic acid it is con
verted into benzoylthebaolquinone which upon digestion with a 15%
solution of sodium ethylate loses the benzoyl group and is converted
into the sodium salt of thebaolquinone identical with the quinone
PHARMACEUTICAL REVIEW. Ill
obtained by Freund which has the constitution of a 3.6-dimethoxy-

4-oxyphenanthraquinone
/\
CH.sO/ \
| I
H0\ /\
Y \co
/\ /co
( Y
I I
CHs.0\ /
\/
Thebaolqulnone
The ethanolmethylamine, HO.CH2.CH2.NH(CHs), was prepared
by boiling the solution of thebaine in benzoyl chloride with alcohol
after dilution with water, filtering off from the benzoic acid and
other insoluble products which separate out on cooling and distilling
the filtrate with steam after making the liquid strongly alkaline
with sodium hydroxide. The volatile base was conducted into dilute
hydrochloric acid and identified as a chloraurate. (Ber. 1906, 16.)
Theobromine.
On adding an excess of theobromine to a solution of lithium oxide
and evaporating under reduced pressure E. Dumesnil obtained theo-
bromine-lithium which can be regarded as theobromine in which one
hydrogen atom has been replaced by one atom of lithium. The
compound corresponds to the formula, C-HiN.iC^Li. and is soluble
in about half its weight of water. Exposed to the atmosphere the
solution of the compound becomes turbid from the separation of
theobromine and lithium carbonate. Dilute hydrochloric acid decom
poses the compound into free theobromine and lithium chloride.
(J. pharm. chim., 1906, 326.)
Tobacco Alkaloids.
Ame* Pictet gives a resume' of the investigations upon the alka
loids of tobacco leaves. The dry leaves were macerated for a short
time in luke warm water and the extract then concentrated in
vacuum. From this aqueous extract which contains about 10 per
cent of nicotine the latter is obtained by adding alkali to the extract
and distilling with steam. By fractionally distilling the crude nico
tine two other bases were obtained, of which one has the formula
CiH»N and goes over below 100°, the other having a slightly higher
boiling point than nicotine is isomeric with nicotine and was named
nicotimine. By shaking out the alkaline aqueous liquid from which

the nicotine has been removed with ether two other bases were ob
tained which were separated from each other by fractional distilla
tion. One of these bases having the formula, C10H12N2, contains
two atoms of hydrogen less than nicotine, is liquid awd was named
nicoteine; the other is solid, has the formula, C10H8N2, and was
named nicotelline. The relative amounts of these alkaloids in the
extract of the tobacco leaves are as follows: For 100 grams of
nicotine, the extract contains 2 grams nicoteine, 0.5 gram nico
timine, 0.1 gram nicotelline and 0.2 gram of the base, CUH9N.
The author thinks that besides these alkaloids there are in
tobacco leaves still other bases and that different varieties of tobacco
contain different other alkaloids.
Nicotixe. The chief reaction which helped to clear up the con
stitution of nicotine was the oxidation of the alkaloid either by
chromic acid (Huber, Ann. 141, 271), or by potassium ferrieyanide
(Cahoues and Etard, Bull. soc. chim. 34, 452), or by the successive
action of bromine and barium hydroxide (Pinner, Ber. 20, 292).
Chromic acid oxidizes nicotine to nicotinic acid (/3-pyridine carboxylic
acid) showing that nicotine is a derivative of pyridine containing
the group, C5H10X, instead of a hydrogen atom in ^-position
CH
HC/ \C—COaH
HC\ /CH
"\/
N
Nicotinic acid
As the radical C5H10 contains one hydrogen atom less than
piperidine it was supposed to be piperidyl pyridine.
NH
/\
H2C/ \CH2
CH f I
HC/ N C HC\ /CH2
Yh
HC\ /CH
Y
Piperldllpyridlne.
When oxidized with chromic acid nicotine loses 4 hydrogen atoms,

giving a compound of the formula C10H10N2 which is optically in
active and unlike nicotine is a monoacid base. The removal of 4
hydrogen atoms destroys the asymmetry of the carbon atom and
changes the diacid nicotine to a monoacid base. The new compound
was named at first isodipyridine (in order to distinguish it from
dipyridine) and was assigned the constitution of a dipyridyl,
C5HsN—CbHsN. When oxidized with bromine and barium hydroxide
nicotin breaks up into nicotinic acid, malonic acid and methylamine.
This indicates that there is in nicotine a methylimide group and
that the other 4 carbon atoms form a normal chain of a pyrrol ring.
For this reason Pinner (loc. cit.) proposed the following formula for
nicotine
H2.C CHa
CH
HC//\c CH\ /CH,
>J.CH3
Yc
HC\ /CH
Y
Nicotine.
regarding the alkaloid as /3-pyridyl-N-methylpyrrolidine. The above
isopyridine would therefore be /3-pyridyl-N-methylpyrrol having the
following formula:
HC CH
CH
HC/ \C C\ /CH
(J-Pyridyl-N-methylpyrrol (Nicotyrine).
This would explain the optical inactivity of the compound as
well as why the base is monoacid (pyrrol, unlike pyrrolidine, having
extremely weak basic properties). The name of isodipyridine was
therefore changed to nicotyrine. The correctness of the above for
mula of nicotine was corroborated by synthesis. The synthesis con
sists of three parts: the synthesis of nicotyrine (/3-pyridil-N-methyl-
pyrrol), the conversion of nicotyrine into inactive nicotine and the
splitting up of the latter into the active components of which the
laevo modification is identical with natural nicotine. The synthesis of
nicotyrine was carried out as follows. Nicotinic acid was converted
by means of Hofmann's reaction into /8-amidopyridine and the latter

distilled with mucic acid. The resulting /2-pyridyl-N-pyrrol when
passed through a red hot tube is transformed into /8-pyridyl-a-pyrrol
CH
HC/ \C—NH2 HO.CO—CH.OH-^H.OH
J + = 4H20 + 2CO2 +
HC\ /CH2 HO.CO—CH.OH-CH.OH
N
HC CH
CH CH
' CH CH
/\ C / /" I I
IK N/ HC/ \C C\ /CH
>
MI
CH CH HC\ /CH
N N
J-Pyrldyl-N-pyrrol. /J-Pyrldyl-«-pyrrol.
The /}-pyridil-a-pyrrol forms a potassium salt which when treated
with methyl iodide is converted into nicotyrine.
In order to reduce the pyrrol ring without reducing at the same
time the pyridine nucleus the nicotyrine was treated with bromine
which enters only the pyrrol ring and the resulting compound re
duced with tin and hydrochloric acid. At first only two atoms of
hydrogen are taken up with the formation of dihydronicotyrine but
when the bromination and subsequent reduction was repeated the
compound was converted into tetrabydronicotyrine or inactive
nicotine identical in every respect with the inactive nicotine which is
formed by heating nicotine sulphate (or hydrochloride) in aqueous
solution for +0 hours to 200°.
The splitting up of inactive nicotine into its active components
was accomplished by the fractional crystallization of the bitartrates.
On mixing one molecule of inactive nicotine with a concentrated
solution of two molecules of dextro tartaric acid in water, the dextro
rotation bitartrate of 1-nicotine crystallizes out on standing and can
be purified by recrystallization from water until the melting point and
the optical rotation remain constant. When this bitartrate is decom
posed by alkali 1-nicotine is obtained identical with the neutral base.
From the mother liquor of the dextrorotatory bitartrate of
1-nicotine a base was obtained (by means of alkali) which when com
bined with laevorotatory tartaric acid gave the laevorotatory bitar.
trate of d-nicotine. On treating this bitartrate with alkali d-nicotine
was obtained.
Physiological tests showed that 1-nicotine is about twice as

poisonous as d-nicotine. This is in accord with observations made
by other investigators in the case of optically active substances, for
example, d-hyoscyamine and their racemic form, atropine.
Nicoteine. Like nicotine, nicoteine, C10H12N2, is a colorless
strongly alkaline liquid base miscible with water in all proportions
and not solidifying at —80° in a mixture of ether and carbon
dioxide. Nicoteine boils at 200—209°, has a specific gravity of
1.077 at 12°, a parsely-like odor and a specific rotation of [a]Dn =
—16°. While the salts of 1-nicotine (natural nicotine) are dextro
rotatory those of nicoteine are leaevorotatory. An investigation of
the constitution of nicoteine showed that it is isomeric with dihydro-
nicotyrine obtained by reducing nicotyrine. As nicotyrine contains
the group, —H=CH—CH=CH—, which by reduction usually changes
to the group, —CH2—CH=CH—CH2—, the formula of this syntheti
cal dihydronicotyrine must be as follows:
HC _ CH
CH I
Hc/X^C HC\ )
I VcHs
Hi:\ /CH
\/
N
Dihydrouiiotyrlne (xynthetic).
(3)
Nicoteine can therefore have either of the two following formulas :
HC CH2 H2C CH2
CH CH
HC/ /\ I
%C—C\ /CHa or /V
HC/ \C-CH\ /CH2
YcHg VUI,
HC\ ^CH HC\ /CH
V \/
N NH
(1) (2)
As nicoteine being optically active must contain an asymmetric
carbon atom formula 2 must be the correct one. When nicoteine is
heated in aqueous solution with silver oxide it is not oxidized but
is i8omerized to dihydronicotyrine, i. e., (2) changes to (3). In
physiological respect nicoteine resembles nicotine but is slightly more
poisonous and does not produce contraction and lowering of the
temperature of the extremities.
NrcoTiMiNE, C10H14N2. This alkaloid is isomeric with nicotine

and resembles the latter in physical properties like odor and boiling:
point. Chemically it differs from nicotine in being a secondary base.
It was separated from nicotine by treating their mixture with
benzoyl chloride in alkaline solution or by nitrous acid. Both the
nitrosamine and the benzoyl derivative of nicotimine still possess
basic properties. As nicotimine does not give the pyrrol reactions
it is supposed to have the constitution of /}-pyridyl-a-piperidine, i. e.,
the constitution formerly ascribed to nicotine.
CH,
/\
H2C/ \CH2
CH !
Hc/^C HC\ JcH2
il !I VNH
HC\ ycH
Y
Nicotimine.
Nicotelline, C10H.8N2. This alkaloid forms prismatic crystals,
melting at 147—148° and boiling a little above 300°. It is difficultly
soluble in water or ether and its aqueous solution has a neutral
reaction. It does not give the' pyrrol reactions and does not
decolorize potassium permanganate in acid solution. It is the only
tobacco alkaloid that forms a difficultly soluble chromate. In many
of its properties it resembles the dipyridines but is not identical
with either of the 4 known dipyridines of which 6 are theoretically
possible.
The base C4H9N. Thise base is obtained by distilling crude
nicotine and collecting the fraction that goes over between 80° and
90°. It is a colorless, very mobile liquid of a strongly alkaline
reaction and a piperidine-like odor. It was found to be identical
with pyrrolidine
H2C CH2
I I
I I
H2C\ /CH2
It is the presence of this very volatile base that gives to ordinary

nicotine the disagreeable ammoniacal odor which disappears upon
rectification.
As by boiling nicotine for 7 hours with a 20 per cent solution of
sodium hydroxide no pyrrolidine is formed it must be assumed that
pyrrolidine exists its such in tobacco leaves and is not formed from
nicotine during the distillation with alkali. Pyrrolidine would there
fore seem to be the simplest vegetable alkaloid both with regard to
formula and constitution. (Arch. Pharm., 1906, .'!75.)
Tropeines.
H. A. D. Jowett and A. C. 0. Haun show that the previously
observed dimmution in physiological activity of pilocarpine upon
the addition of potassium hydroxide also occurs in the case of
terebyltropeine and phthalideearboxyltropeine.
(CHs)».C CH.CO.P
CH.CO.P
0 /CH« r h / n
l6H'v°
CO CO
Tertiyltropelne. Phthalldecarlmxyl tropeine.
(I) (II)
(P stands here for the nitrogen — containing nucleus.)
It is also shown that Ladenburg's generalization that only those
tropeines have mydriatic action which contain a benzene nucleus in
the acyl complex does not hold good in the case of terebyltropeine
which has a distinct mydriatic action. In general it was found that
the most favorable conditions for the developement of mydriatic
action in a tropeine are those stated by Ladenburg, namely, that
the acyl group should contain a benzene nucleus and an aliphatic
hydroxyl in the side chain containing the carboxyl group. This is
shown by the fact that three other tropeines, namely, protocate-
chyltropeine, methylparaconyltropeine and glycollyltropeine had no
mydriatic action at all.
Glycollyltropeine, CHa(OHi.ClO.CsHnON, was prepared by La
denburg's general method (Ann. 1883, 217, 82) and purified by
converting it into the hydriodide, recrystallizing the latter from
methyl alcohol, then setting the base free and recrystallizing it from
benzene. The tropeine forms laminar crystals melting at 113—114°,
which are soluble in alcohol and water, but insoluble in ether. The
hydriodide separates from methyl alcohol in stout acicular crystals
melting at 187—188°, which are soluble in water, difficulty soluble
in alcohol, and insoluble in ether. It contains half a molecule of
water of crystallization which cannot be removed by heating to
110°. Higher temperatures decompose it. A nitrile melting at
120—121°, an aurichloride melting at 186—187° and a plantiui-
chloride melting at 225—226° were also prepared.
Methylparaconyltropeine,
CHs.CH— CH.CO.CsHiiON
I I
O.CO.CH2
as well as the remaining tropeines ilescribed in this paper, was pre
pared by passing hydrogen chloride through a solution of tropine
neutralized with the acid in question and maintained at a tempera
ture of 120—125° for two to three hours (Tiiuber, D. R. P., 95,853).
The dark brown gum thus obtained was decomposed by ammonia
and the base extracted with chloroform ; the crude tropeine was
purified by conversion into the hydriodide. The pure base, regener
ated from the hydriodide, forms a colorless oil. A hydriodide of
this tropeine melting at 177—178°, a hydrobromide melting at
196—197°, an aurichloride melting at 64—05° and containing one
molecule of water of crystallization, an amorphous platinichloride
melting at 233—234° and a picrate melting at 190—191° were pre
pared.
Terebyltropeine (I) forms diamond-shaped crystals melting at
66—67°, which are easily soluble in water or alcohol. A hydro
chloride in the form of leaflets which soften at 80° and melt at 82°,
a hydrobromide in the form of laminar crystals melting at 230° to
231°, an aurichloride forming imperfect crystals which melted in
definitely at 85—86° and contained a molecule of water of crystal
lization, a gelatinous platinichloride and a picrate, melting at 198°
to 199°, were prepared.
Phthalidecarhoxyltropeine (II) was purified through the hydro
bromide and recrystallized from ethyl acetate. It crystallizes in
square, laminar crystals melting at 79—80° and forms a hydro
chloride melting at 79—80° and forms a hydrochloride melting at
242—244°, a hydrobromide in the form of glistening leaflets melting
at 128—129°, a nitrate containg a molecule of water of crystalliza
tion and melting at 169—171°, an aurichloride melting at 184— 185°
and an amorphous platinichloride melting at 235°.
Protocatechyltropeine, ( "oH3(OH )a.( 'O.CsH 14i >N, forms stout aci-
cular crystals which are sparingly soluble in water or alcohol and
melt at 253—254°. It forms a hydrochloride not melting below
300°, a nitrate which is so easily oxidizable that it was not further
investigated, an easily reducible aurichloride, a platinichloride melt
ing at 228—229° and a picrate melting at 260—262°. (J. Chem.
Soc., 1906, 357.)
NoKTHWESTERN UNIVERSITY .SCHOOL OF PHARMACY.
PH A KMA CE I T1CAL KEY IE IV. 119
Plant Pigments.*
By 1. W. Brandel
Color of Color of Color ol

CORNACEAE.
Corn us mascula 86 ..Stein
Crccifebae.
Cheiranthus Cheiri*1 ..Marquart purple
" " 88 .Perkin yellow
Cheiranthus scopariussn ..Marquart violet
Cheiranthus ( Levkoy )00. .Elsner red decolorized violet
Erysinum perofak*i ..Vogel yellow
Fumaria officinalis92 ..Vogel rose
Hesperis matronalis93... .Vogel violet
Iberis u mbella tao* ..Eisner red colorless violet
Ibeiis violacea05 .Vogel blue
Ericaeae.
Azalea pontics w .Marquart yellow yellow
" " 97 .Vogel rose
Rhododendron arftoreum98..Marquart dark red
Gentianeae.
Gentiana acanlis" Marquart blue green
Geraniaceae.
Geranium Brandel lightrod yellow red
Geranium Brandel dark red light red dark red
* Continued from page 7H.
■« Contains glucoside rutin which yieldH <iuercetln (.lourn. f. pr. ( hem. 83,
p. 851.
»t Contains yellow as well ns purple pigment (Arch. il. Pharm. 56, p. 257).
ss Contains quercetin and isorhnmnetin (Chem. News 74, p. 278).
s8 Flowers arc at first yellow, gradually becoming orange then violet (Arch,
d. Pharm. 56, p. 2<30.
so A(|ueouH Hotation gives blue prec. with lead acetate and violet prec. with
zinc chioride (Chem. Centralbl. a, p. 570).
°( Not changed by ammonia iSitzb. d. Acad. Muenchen 1870, I, p. 17).
»2 Has strong add reaction (Sllzb. d. Acad. Muenchen 1879, p. 19).
»» Has acid reaction (Sltzb. d. Acad. Muenchen 1879, p. 19).
s* A(|ueouH solution gives green prec. with lead acetate and yellow prec. with
tine chioride (Chem. Centralbl. :t. p. 570).
»« Turned green with ammonia (Sltzb. d Acad. .Muenchen 1870, p. 17).
»« Arch. d. Pharm. 5(i, p. 248.
»' Alcoholic solution has strong acid reaction (Sltzb. d. Acad. Muenchen 1H79,
P. 19).
ss Stronglv acid (Arch. d. Pharm. 56. p. 250).
ss Arch. d. Pharm. 56, pp. 249, 259.
Color of Color ol Color of
Geraniaceae.
Geranium sanguineumi Eisner red light red red
" " 2 Marquart red
Geranium robertianums Vogel red
Impatiens balsamina 1 Eisner red
" " a Vogel red
Trompaeolum majus Brandel red yellow red
" " Brandel yellow yellow yellow
Trompaeolum coccineum 3 . . . .Vogel red
Pelargonium peltatum Brandel dark red red dark red
Pelargonium zonale Brandel pink colorless red
Pelargonium zonale Heter- Brandel red colorless red
anthe Brandel red pink red
Pelargonium species* Elsner red colorless red
Pelargonium zonale^ Filhol red light red
Pelargonium inquinanss Filhol red light red
Hypericineae.
Hypericum perforatum 0 Buchner red colorless red
Iiudeae.
Crocus maesiacus7 Marquart yellow
Crocus sativus& Schueler
Gladiolus species^ Elsner red colorless blue
Iris pnmila 10 Marquart violet colorless violet
Iris pumila pnrp.11 Hunefeld
Iris hortensis*2 Hunefeld blue amethyst
1a Hunefeld
Iris hispanica 12 Hunefeld blue amethyst
Ixia croca ta 14 M u rquart orange
Lamatae.
Ajuga reptans 1 s Marquart blue colorless green
" ia Vogel blue
Cedronella cana Brandel spotted
with red colorless colorless
i Aqueous solution gives yellow precipitate with lead acetate (Chem. Centralbl.
3, p.a 570.
Aqueous solution gives lilac precipitate with zinc chioride CArch. d. Pharm.
50, »p. Alcoholic
252). solution has strong acid reaction (Sltzb. d. Acad. Mueuchen, 1879,
p. 19).
* Chem. Centralbl. 3, p. 572.
3 Red aqueous solution is turned blue by ammonia (Compt. rend. 89, p. 196).
« Residue turned green with alkalies (Ben. Jahresh. 11, p. 279).
i Alcoholic residue soluble in water (Arch. d. Pharm. 50, p. 258).
s Contains esters of phytosterin (Bot. Centralbl. 87. p. 152>.
» Solution gives red precipitate with zinc chioride and dark green with lead
acetate (Chem. Centralbl. a, p. 570).
i« Turns red with acids, blue with little alkali, green with excess (Arch. d.
Pharm. 50, p. 244).
tt Gives bluish-red solution with ether-alcohol (Journ. pr. Chem. 16, p. 70).
Journ. pr. Chem. 9, p. 238.
ts Contains iron and manganese (Journ. pr. Chem. 10. p. 84).
'* Contains a red and a vellow pigment lArch. d. Pharm. 56, p. 257).
>s Arch. d. Pharm, 50. p. 258.
i« Turned green by ammonia (Sltzb. d. Acad. Muenehen 1870, l, p. \~).
Obserrer. flower. ale. sol. residue.
Labiatae.
Dracocephalum altnicum 17...Marquart blue blue
" '• if* Vogel lilac
Hyssopus officina lis 1 8 Vogel blue
" " no Vogel white
" " 20 Vogel rei I
" " ai Vogel blue
Lamium purpureum2i Vogel red
Lamium maculatum22 Vogel red
Lophanthes unisatus Brandel blue colorless colorless
Monarda didyma Brandel purple colorless red
Monarda flstulosa Brandel purple colorless red
Monarda coccinea 23 Eisner red colorless red
Monarda ecarlate2* Belhomme scarlet
Nepeta cataria as H unefeld
Physostigea Virginia na Brandel purple colorless yellow
Pycnantliemum nmticum Brandel purple
spots colorless colorless
Salvia splendens Brandel red colorless red
" " ae Filhol red
Salvia nemorosa20 Brandel blue colorless blue
Salvia Pitcheri Brandel light blue colorless yellow
Salvia azurea Brandel light blue colorless yellow
Salvia coccinea Brandel red faint pink deep red
Salvia variegata 27 Hunefeld
Salvia cardinalis28 Vogel red
Salvia officinalis-9 Vogel blue
Salvia nobilis3i) Vogel blue
Salvia pratensis*i Vogel blue
Scu t tela ria altissima B ran del light blue colorless blue
Stachys palustris 32 Vogel red
Stachys sylvestris 32 Vogel red
Thymus serphyllium 32 Vogel red
1 7 Aqueous solution turned lilac with boric acid (Arch. d. Pharm. 56, p. 248).
II umed light green by ammonia (Sltzb. d. Acnd. Muenchen, 1870. I, p. 17).
It Alcoholic solution has neutral reaction (Hltzb. d. Acad. Muenchen. 1879,
p. 19).
ao
•-'t Not changed by ammonia (Sltzb. d. Acad. Muenchen, 1870, I, p. 17).
Same as 26.
tt Alcoholic solution has strong acid reaction (Sltzb. d. Acad. Muenchen. 1879,
p. 19)
as Solution gives red precipitate with lead acetate (Chem. Centrolbl. 3, p. 572).
■4 Contains carmine identical with carmine from co hineal (Compt. rend. 43,
35 ).Joum. pr. Chem. 9, p. 217.
p. 382
2n Turned blue by alkalies (Compt. rend. 43, p. .145).
37 .fourn. pr. Chem. 9. p. 217.
Turned blue by ammonia (Sltzb. d. Acad. Muenchen. 1870, I, p. 17).
Not changed by ammonia (Sltzb. d. Acad. Muenchen, 1870, I, p. 17).
Alcoholic solution hus neutral reaction (Sltzb. d. Acad. Muenchen, 1879.
19).
si , ihollc solution has fnlntly acid reaction (Sitzb. d. Acad. Muenchen, 1879,
19).
»» Alcoholic solution has strong acid reaction (Sltzb. d. Acnd. Muenchen, 1879,
19).
122 PHA RMA CE UTICA L RE VIEW.
Color of Color ol Color of
Observer. flower. ale. BoI. residue.
Leouminosae.
Cassia lignstrinn 3a Marquart yellow yellow
Clitoria tenia ten Brandel blue blue blue
Coronilla vnrin, 84 Vogel violet
" •' as Vogel red
Bu ten frondosn 30 Hum mel
Hedysarum ooronariums~ ....Elsner red colorless violet
Lathytus odoratus Brandel purple colorless purple
" " Brandel pink colorless pink
Lathyrus latifolius™ Eisner red colorless violet
Lathyrus tingitanus3? Marquart red
Lupinus cruicksbankii 40 Marquart blue
Lupinus mutnbilis*i Marquart red
Lotus corniculatus*2 Vogel yellow
" " <3 Vogel yellow
Genista tinetoria 44 Hunefeld
Medicago sat/ra*5 Vogel blue
Pisum sativum 48 .....Vogel violet
Phaseohis mult iflorns 47 V ogel red
Podalyrin australis** Marquart blue green
Robioia bispidia*9 Eisner red colorless red
Robinia pseudacacin 50 Zwenger
Spartinm scopnrium nl Hunefeld
Sophora japonica 52 Rochleder yellow
•' " 58 Sehunck yellow
Trifolium pratense, L Brandel red colorless vellow
Trifolium pra tense 54 Vo<rel red
Trifolio m agrestis 47 V oprel red
Yiven fnba 55 Marquart
a» Pigment difficultly soluble in ubsol. alcohol and ether (Arch, d. l'harm., 56,
p. 248).
»* Not changed by ammoiiln (Sltzb. d. Acad. Mnenehen. ls~0. I. p. 17).
as Mhk HtronK acid reaction (Sltzb. d. Acad. Muenchen, 1871*, p. 19).
a« Contains a glucoside (.Bur. 1890, p. 658).
a' Chem. Centralbl. 3. p. 570)
•» Solution gives orange prec. with zinc chioride and yellow prec. with lead
neetate (Chem. Centralbl. 3. p. 570).
»• Solution gives purple prec. with zinc chioride (Arch. d. Pharm. 56,
p. 252).
*" Flowers are at first white changelng to blue (Arch. d. Pharm. fi(5.
p. 261).
«> Flowers are at first white changelng to red (Arch. d. Pharm. 56, p. 262).
*2 Same as H4.
*» Solution has acid reaction (Sltzb. d. Acad. Muenchen. 1879, p. 19).
** Contains iron (Journ. pr. Chem. 16. p. 84).
*5 Solution has faint aclil reaction (Sltzb. d. Acad. Muenchen. 1879. p. 19).
*« Turned green by ammonia (Sltzb. d. Acad. Muenchen, 1870, I, p. 17).
*» Arch.
Solution has strong
56, acid reaction (Sltzb. d. Acad. Muenchen, 1879. p. 19).
*s d. Pharm. p. 25:t.
*» Solution gii-e.s blue-green prec. with lead acetate, red with zinc chioride
(Chem. Centralbl. a. p. 572).
oo Contains glucoslde roblnine (Ann. Suppl. I. p. 257).
s> Contains iron (Journ. pr. Chem. 16, p. 84).
as Contains quercctin (Chem. Centralbl. 80, p. 166).
»» Contains gluco.dde rutin (Journ. Chem. Soc. 67. p. 30).
»* Not changed by ammonia (Sltzb. d. Acad. Muenchen, 1870, I, p. 17>.
" Arch. d. Charm. 56, p. 259.
PHAKMACEl TICAh REVIEW. 123
Color of Color of Color o!
Observer. rtower. air. sol. residue.
LlUACEAE.
Allium nigrum™ Marquart black
Allium seJioenopross1 Vogel light red
Fritillaria imper.5* Hunefeld red
Hemerocallis /i;/ra59 Marquart orange
HyaciutheiM Hunefeld red and blue
Hyacinthus botryoidesul Stein blue
Lilium tigrinum splendens.. ..Brandel orange yellow pink
Lilium candidum02 Hunefeld
Scilla sibirica*3 Marquart blue colorless
Scilla amoena0* Hunefeld
Scilla campanulata 04 Hunefeld
Tulipa ovulus soles w Marquart red
Veritt.rum nigrum60 Marquart brown
LlNE.E.
Linum perenne'" Marquart blue
" «8 Vogel blue
" 8» Vogel blue
Linum syrincum™ Vogel blue
Louamace.e.
Badleia globosa10 Marquart yellow
Lythrahie.*:.
Lagerstroemia indira Brandel purple slightly pink red
Malvace.*.
Althaea rosea Brandel red slightly brown darkred
Althaea rosea 71 Elsner purple partlydecol. purplered
" 72 Hanausek
" 7» Glan red
" 7* Vogel rose
" "i Vogel light violet
Arch. d. Pharm. Till, p. 258.

. ■'■» Turned
ContainHitrwn
red by
andnmmonla (Sltzb. d. Turpentine
yellow pigment. Acad. Muenchen, 1870.outI, p.red17).pigment
dissolves
forming colorless solution (Jonrn. pr. Chem. It), p. 68).
"»
so Contains
Turpentinereddissntves
and yellow pigments
pigmcntH to (Arch d. Pharm.
colorless solution56.i.Iourn.
p. 257).pr. Chem. 1<>,
p. 68).Turned red with hydrochioric ncid (Journ. pr. ( hem. Sit. p. 495).
« Contains iron i.Iourn. t. prakt. Chem. 16, p. 81.).
"3 I'orms colorless solution with 40 p. c. alcohol (Arch. d. Pharm. .">(!, p. 247).
«i Journ. pr. Chem. it, p. 217: 16, p. 84.
«s Cross section shows three layers. inner one Is colorless, two outer ones blue
or red (Arch. d. aPharm.
blue pi 56. p. 256).
•« Contains meiit (Arch. d. Pharm 56, p. 2.1si.
es beclorlzed by ammonia 24!).
Arch. d. Pharm. 56, p. (Kltzh. d. Acad. Muenchen, 1870, I, p. 17).
Alcoholic solution has neutral reaction (Sltzb. d. Acad. Mueuchen, 1879,
|). 19).
'« Alcoholic extract is soluble In water (Arch d. Pharm. 56. p. 258).
»> Aqueous solution gives violet precipitate with line chioride, blue-green prer.
with lead acetate (Chem. Centralbl. 8, p. .">70).
" Bot. Centralbl. 25. p. 254.
'3 Contains a glucoslde (Bot Centralbl. Belhed 8, p. 292).
7* Turned green by ammonia (Sltzb. d. Acad. Muenchen, 1H70, 1. p. 17).
124 PHARM ACELTWAL REVIEW.
Malvaceae.
Althaea rosea1s Vogel dark violet
Anoda hastata Brandel blue colorless blue
Gossypium harbaceum70 Perkin yellow
Hibiscus syriacus Brandel purple colorless purple
" Brandel white colorless colorless
" " Brandel blue colorless blue
Hibiscus rasa sinensis Brandel purple pink purple
Hibiscus syriacus77 Fremy blue colorless blue
Lavateria trimestris78 Vogel rose
Malva rotundifolia Brandel rose colorless colorless
Malva sylvestris " Elsner red colorless red
" '• 74 Vogel rose
Malva rosea*0 Hunefeld
Malva rotundifolia8i Vogel rose
Myrtace.e.
Metrosideros lanceolata*'2 ....Elsner red colorless red
Metrosideros semperflorens83 Vogel red
NYCTACilNACE.E.
Mirabilis jalapa Brandel red slightly yellow yellow
" Brandel pink colorless yellow
" Brandel yellow yellow yellow
Onaoraiue^:.
Gaura biennis** Marquart white
Fuchsia proenmbens
(Red part) Brandel red colorless purple
Fuchsia procumbens
(Purple part) Brandel purple pink purple
Oenothera acaulis85 Marquart white
Oenothera speciosa, Nutt.*5 Marquart white
Oenothera granditiora89 Hunefeld
Oenothera*' Vogel yellow
Orchide.e.
Orchis vernus88 Marquart red
Orchis coriophora, D.8"
" Not changed by ammonia (Hitsb. d. Acad. Muenchen, 1870, I, p. 17).
7« ContainH glucoside which yields goHsypetine (.Tourn. Chem. Hoc., 1899, p. 82;").
" Journ. de Pbarm. (8) 25, p. 249.
is Turned blue by ammonia (Sltzb. d. Acad. Muenchen, 1870. I. p. 17).
'» Ureen prec. with lead acetate, red with line chioride (Chem. Centrnlbl. 3,
I>. s0 Contains
)■ iron (Journ. pr. (.'hem. 16, p. 84).
St Has stroug acid reaction (Sltzb. d. Acad. Muenchen, 187!). p. 19).
»»
ss Chem. Centralbl.
Alcoholic solution3,has
p. 572.
strong acid reaction (Sltzb. d. Acad. Muenchen, 1879.
p. 19).
s+ Flowers change to red upon fading (Arch. d. Pharm., 56. p. 262).
»s White dowers gradually change to red after having blossomed for a time
(Arch. d. Pharm. 56, p. 262).
»« Contains
s7 iron by(Journ.
Not changed f. pr.(Sltzb.
ammonia Chem. d.16,Acad.
p. 84).
Muenchen, 1870, I, p. 17).
Flowers become blue on fading <Arch. d. Pharm. 56, p. 263).
»» Probably contains caprouic add (Compt. rend. 58, p. 689).
Color ol Color of Color ot
Observer, flower. ale. sot. residue.
OXALIDE.K.
Oxalis tetraphylla90 Vogel rose
Papavebace.e.
Papaver bracteatum9i Marquart dark red
Papaver nudicaule02 Marquart yellow
Pu paver rhoeas93 Elsner red colorless red
" »* Filhol red
" 90 Vogel red
Papa ver somniferum 98 Hunefeld red
96 Hunefeld white
95 Vogel red
Papaver burzerii91 Weiss yellow
Papa ver pyrenaicum 97 Weiss orange-red
Plumbagine.e.
Ceratostigma plumbageoides Brandel blue slightly slightly
yellow pink
Polemoniace.e.
Polemonium coeruV. granditi ..Hunefeld
Gilgia aggregata9S Hunefeld
Polygale.e.
Polygala vulgare99 Hunefeld
Polygala amarai Vogel blue
Primclace.e.
Anagallis arvensis2 Vogel red
Lysumachia numulariaa Vogel yellow
Primula veris* Hunefeld yellow
Ranunculace.e.
Aconitum napellus5 Vogel blue
Aconitum vulgare0 .'Marquart blue green
Aquilegia vulgaris"7 Hunefeld
»o Turned blue by ammonia (Sltzb. tl. Acad. Muenchen, 1870. I, p. 17).
»' Alcoholic solution baa ncld reaction (Arch. d. I'darm. 56, p. 250).
" Alcoholic residue soluble in water (Arch. d. Pharm. 56, p. 250).
»» Aqueous solution gives violet precipitates with lead acetate and zlnc chioride
(Chem. Centralbl. 3, p. 572).
»* Turned blue by alkalies (Compt. rend. 50, p. 545).
Alcoholic solution has strong acid reaction '(Sltzb. d. Acad. Muenchen, 1879,
p. 19). Contains iron (Journ. pr. Chem. 16. p. 84).
»7
»b Contains
Journ. pr.yellow
Chem. crystalline
9, p. 217. pigment (Bot. Centralbl. 21, p. 101).
»» Journ. pr. Chem. 9. p. 217.
t Alcoholic solution has a faint acid reaction (Sltzb. d. Acad. Muenchen, 1879,
p. 19).
2 Alcoholic solution has strong acid reaction (Sltzb. d. Acad. Muenchen, 1879,
p. 19).
» Alcoholic solution has acid reaction (Sltzb d. Acad. Muenchen. 1879, p. 19).
* Forms yellow solution with ether (Journ. pr. Chem. 16, p. 69i.
» Alcoholic solution has faint acid reaction (Sltzb. d. Acad. Muenchen, 1879,
p. I 9).
« Arch. d. Pharm. 56. p. 253.
' Journ. pr. Chem. 16, p. 78.
(To be continued.)
126 PHA RUACEUTICAL REVIEW.
Literary.
Books Reviewed.
A Critical Revision of the Gems Eucalyptus, by J. H. Maiden,
Gov. Botanist of New S. Wales and Director of Botanic Gardens,
Sidney. Part IX, pp. 259—294.
In this part eight species are described and illustrated, making
the total number of species which have been included in this excellent
work of Mr. Maiden's to date, thirty-one. This fascicle is illustrated
by four large plates showing the leaves, flowers and fruits of the
species described. R. H. It.
American Root Drugs, by Alice Henkel. Bull. 107. Bureau of

Plant Industry, Washington 1). C.
In this bulletin Miss Henkel describes fifty of our commoner root
drugs, including all the U. S. P. root drugs grown in this country.
The common and official names are given for each of the plants,
also habitat range, descriptions of the plant and the drug, methods
of collection nnd preparation, prices and uses.
The bulletin is well illustrated by seven plates taken from nature
and numerous figures in the text.
It will be especially valuable to drug collectors, who sometimes
gather the wrong plants unintentionally. R. H. D.
The Supposed Relationship of White Snakeroot to Milksickness,
or "Tkem bless.'" A. 0. Crawford, U. S. Department of Agri
culture, Bureau of Plant Industry, Bulletin No. 121, part I.
The author has subjected to the test of experiment the assertion
that white snakeroot (Eupatorium ageratoides, L. F.) is the cause
of miiksickness or "trembles." Intravenous and subcutaneous in
jections into rabbits of aqueous extracts of the dried plant and
of its ash were not followed by signifiant symptoms. Administration
to cats, dogs and man (the author) did not cause the symptoms of
miiksickness. The incidence of the disease suggests that it is of
parasitic origin. J. Erlanger.
The Use of Suprarenal Glands in the Physiological Testing

of Drug Plants. By A. C. Crawford, U. S. Dept. of Agri.
culture, Bureau of Plant Industry, Bulletin No. 112, Aug. 10,
1907.
The paper consists almost exclusively of a review of the literature
dealing with the composition, physiological action of, and methods
of standardizing the active principle of the suprarenal glands, and
presumably is intended to serve as the basis for the development of
a method for testing, by comparison with epinephrin, the physio
logical activities of certain drug plants. In addition the author
gives briefly the technique employed in his laboratory for these pur
poses. •/. Erlanger.
Jahresbericht der Pharmazie, herausgegeben vom deutschen Apo-
thekerverein. Bearbeitet von Dr. Heinr. Beckurts unter
Mitwirkung von Dr. H. Frerichs and Dr. H. Emde. 41.
Jahrgang, 1906. (Der ganzen Reihe 60. Jahrgang). Ein Bd.,
pp. IV, 615. Vandenhoeck und Ruprecht. Goettingen,
1907. M. 20.00.
So useful and so well known a work as the ''Jahresbericht"' calls
for no review. A mere notice that it has made its appearance upon
the book market ought to suffice,. Yet there are so many pharma
ceutical institutions of learning, to say nothing about pharmaceutical
practitioners, who have managed to get along without it that per
sons who have long come to regard it as indispensable cannot but
wonder. Its merits are evidently not sufficiently appreciated in spite
of the numerous favorable reviews that have appeared year after
year. «
To the editor who does not want to repeat himself annually or
who is not content with platitutes, the problem of a review each
twelve month is a serious one indeed. And yet the character of the
"Jahresbericht" is so manifold that one has but to open the volume
to find something of interest on nearly every page. Even the index
is not only useful but interesting as well.
Thus the "Jahresbericht" for 19(Xi contains not far from three
thousand authors' names and over four thousand subject primes.
Taking a few subjects at random, we find e. g. that camphor is
mentioned nine times. Its preparation, its cultivation in Italy, its
adulteration, its determination in alcoholic solution etc. and other
aspects of camphor problems on which pharmacist or chemist may
desire up-to-date information will be found here. The hosptital
pharmacist who must keep posted on the progress made in the
examination of urine will find no less than thirty-two [references in

the index. The food chemist will find twenty-four references to
butter, sixty to milk, thirty-one to water, etc. The pharmaceutical
practitioner will find among the twenty-three references to tinctures
one pertaining to the incompatibility of Compound tincture of
cardamoms with alkaloids, another on the addition of borax to
Tincture of iodine to prevent the irritation caused by hydriodic
acid formed, a third to the adulteration of Tincture of valerian etc.
Thus a variety of interests are served by the "Jahresbericht.''
One of the most commendable features of the "Jahresbericht'' for
1906 is its early appearance, it having been ready in the fall of
1907. It is due to ffhe writers absence for the past half year that
this notice has not appeared sooner. May this useful annual find
an ever increasing number of friends who are willing to be served
by it. E. K.
PROCEEDINGS OF THE AMERICAN PHARMACEUTICAL ASSOCIATION at
the fifty-fifth annual meeting held at New York, N. Y.,
September, 1907. Published by the A. Ph. A., Baltimore,
1907.
To the writer at least, the feature of this year's Proceedings
which most deserves special mention is its dedication, as it were, to
Albert E. Ebert whose half-tone portruit serves as frontispiece.
Since 1864 a member of the Association, he was its President during
the association year 1872— '73. There is possibly nothing inherently
striking in a long membership and a tenure of office as President.
A few others may be able to look back upon a like record. What
makes both noteworthy are two things: firstly, that Mr. Ebert's
interests in the Association in no way abated after he had occupied
the highest office within the gift of the Association; and secondly,
that his brief tenure of office was marked by a gift such as no
American pharmacist has duplicated.
The Ebert Prize, based on an original donation of $500.00, now
amounting to $900.00, is the only gift of its kind in this country.
Mr. Ebert never was a rich man, but his devotion to pharmacy
becomes even more apparent from the fact that at his death he
bequeathed all he had to the Association. Though the sum be small
the spirit is such as no one has previously displayed. Whatever his
faults, no matter how he occasionally emphasized commercial
pharmacy, he has done more, in a way at least, for scientific
pharmacy than any one else, he gave all he had. E. K.
Volume 26. MAY, 1908. Number 5.
Some Chemical Remarks on the Citro-Compounds of Iron.
By ./. E. Gerock.
In the October number of this journal* there appeared an article

by A. B. Stevens on the citro-compounds of iron concerning which
the writer desires to make the following additional statements.
The class of preparations to which these compounds belong are
not used in European pharmacy. However, the writer was induced
to investigate them not long ago by a physician who was interested
in their composition.
The National Formulary, while it gives a method for the pre
paration of these compounds, states nothing about their chemical
composition. In order to acquire an insight into their chemical
nature a number of experiments were made, a detailed account of
which is not essential to these considerations. Suffice it to state
that while the time was too short to make as an elaborate in
vestigation as did Professor Stevens of the ratio of iron iodide and
potassium citrate, the writer obtained figures coming close to those
of this investigator. The conclusions arrived at were the following:
In order better to appreciate the situation it should be re
membered that citric acid contains three carboxyl groups and one
hydroxyl group, also that if the carboxyl hydrogens are displaced
by alkali metals several heavy metals are known to reveal an in
clination to replace the hydroxyl hydrogen. That in this peculiar
behavior, the relative position of the hydroxy group or groups of
such hydroxy acids plays a r61e, need only be mentioned here with
out going into this subject at length. That which is of particular
interest, however, is the apparent fact that the metal after having
replaced the hydroxy hydrogen is not in the ionic state. It is
• Vol. 25, p. 299.
(129)
13) 1'HARUACEDTICAL REVIEW.
hidden, as it. were, within the radicle and does not possess the
properties of the like element when constituting the basal portion
of a salt. Such a molecule as the above mentioned must rather be
regarded as the alkali salt of a ferri-organic acid. Copper, silver,
mercury, and other metals are able to form similar metal-organic
combinations. The ordinary reactions, therefore, e. g., for iron in
this case, naturally fail until the organo-ferric structure is interfered
with by a stronger acid, when it is again converted into ionic iron
of the salt-forming state.
The reactions involved in the process of preparation may, there
fore, be described as follows: The ferrous iodide dissolves a third
atom of iodine and, whether it combines with it in a strictly
chemical sense or not, now acts like ferric iodide, the iron being
trivalent. Citrate of potassium being added, double decomposition
may be regarded as taking place with the formation of potassium
iodide. The ferric iron, however, does not take the place of the dis
placed potassium, but steps into the places of the hydroxyl
hydrogens, whereas these in turn step into the places of potassium,
reconstituting the carboxyl groups. The result is a complex mole
cule, the several citric radicles being held together by the ferric iron.
The simplest phase of this reaction can possibly be expressed by the
following equation :
Fe'"Is+3C.tHt.0H.(C00K)3 = 3KI + l'V"(0.CsH4).t.( (00H )s.(COOK)«
Practically, however, the reaction may be regarded as more

complex. What is more important is that in the above instance we
have but a specific case of a general law. While many illustrations
of its working are known, it is still more frequently misunderstood.
In many instances where double salts are assumed, the peculiar be
haviour of metals with regard to oxyacids, of which the above case
affords but an illustration, might lead to a more rational view.
As a classical instance Fehling's solution may be mentioned.
The hydroxy acid is tartaric acid, potassium and sodium are the
alkali metals, copper the metal which replaces the hydroxy hydrogen
atoms. Unfortunately but few definite compounds of this nature
have thus far been isolated in a sufficient state of purity to admit
of analysis, to say nothing about the exnct working out of a
structural formula.
Nevertheless, the properties of these compounds are best inter,

preted by the assumption of such a metal-organic acid radicle as
indicated above and herein lies the justification of the hypothesis
adopted.
Strassburg-Xeudorf, Nov., 1907.
Oitro-Compoands of Iron.
By A. B. Stevens.
I have been much interested in the conclusions reached by Mr.

Gerock upon the position of the iron in the so-called citro-iodide of
iron. My previous paper referred especially to the method of pre
paration, rather than the chemical nature of the resulting compound.
Incidentally I referred to the work done by others and becoming
interested in the chemistry of the substance I proposed to investi
gate it further. In fact I have commenced work upon it but owing
to the pressure of a multitude of other duties am unable to push
the work as rapidly as I desire. I have for some time entertained
the idea that the iron excisted in the form of a ferricitric acid, per
haps somewhat similar to the ferricyanides. The theory advanced
by Mr. Gerock is very plausible. The formula given however calls
for three molecules of citrate to one atom of iron in the ferric con
dition. Since citric acid has only one hydroxyl group it is difficult
to see how ferric iron can unite with less than three of the citrate,
unless part of the iron is combined with some of the carboxyl
groups. The amount of citrate actually required for each atom of
iron is half that required for Gerock's formula. By replacing the
hydrogen in his three carboxyl groups with iron.
Fe(C.iHi0)3.(C00H)s.(C00K)B becomes Fe(C3H*0)s.(nOO)3Fe.(COOK)6.
Which is the proportion actually required.
I appreciate Mr. Gerock's suggestion and will bear it in mind
during future experiments.
The Estimation of Hydrastine.*
By W. A. Pnckner.
The assay of fluidextract of hydrastis. While H. M. Gprdin and A.

B. Prescott1 have based methods of estimating berberine upon the
insolubility of berberine iodide, commonly called berberine hydro-
iodide, I have based on this insolubility the separation of berberine
from hydrastine prior to the estimation of the latter. The method
which I have used for the hydrastine estimation in fluidextract
of hydrastis has been included in the 8th revision of the United
States Phurmacopeia, but with the modification that an aliquot part
is used for the assay. Experiments showing the results obtained
by the method as I have used it for considerable time and in which
the use of aliquot portions is avoided as compared with the results
obtained by the method now official, may be of some interest at
this time.
In the results given below, the official method has been inter
preted as follows:
Method a : 10 cc. fluidextract is measured into a volumetric
flask, a mixture of water 75 cc., potassium iodide T. S. 10 cc. added,
and, after mixing, sufficient water to make 100 cc. After several
minutes the mixture is filtered through paper and 50 cc. of the
filtrate are transferred to a separator. Ammonia water is added
until the liquid is alkaline toward litmus paper, 0.1 cc., or 3 drops
being usually sufficient, and then ether 30 cc. ; after agitation the
aqueous liquid is drawn into a beaker and the ether transferred
through a very small pledget of cotton to a tared beaker. The
aqueous layer is transferred back to the separator, shaken with
ether 20 cc. and after separation the aqueous layer is rejected. The
ether is added through the funnel, to the first ether extraction, and
the neck of the separator and the stem of the funnel washed with
* Contribution from the Chemical Laboratory of the American Medici 1 Associa
tion.
t J. Am. Chem. Hoc., 1899, vol. 21, p. 732; Proc. : A. Ph. A, 1899, vol. 47,
p. 260.
5 cc. ether. The ether is allowed to evaporate in a warm place (so

as to avoid condensation of water by the cold produced in the
vaporization of the ether), and the residue then dried in an oven at
95 to 98 degrees so long as further loss in weight is noted.
The method of assay, which I have used, in which the use of
aliquot parts is avoided and in which a more complete extraction
of the alkaloid by ether is aimed at, is carried out as follows:
Method b: Into a beaker containing water, 25 cc. and potassium
iodide T. S., 5 cc., fluidextract 5 cc., is measured. The mixture is
stirred well and filtered through a 7 cm. filter into a separator. The
precipitate on the filter is washed with two portions, 5 cc. each, of
a mixture consisting of water 19 cc. and potassium iodide T. S.
1 cc. When the precipitate has drained, it is transferred with its
filter back to the beaker and mixed with 5 cc. of the wash fluid
above used. This is poured on a new filter, the filtrate passed into
the separator and the beaker and precipitate washed with the
remaining 5 cc. of the wash fluid. The liquid in the separator is
made alkaline with ammonia water, usually 0.1 cc. or three drops
being sufficient, and extracted with three portions of ether, 20 cc.
each; the aqueous solution being passed successively through three
separators, each containing 20 cc. of ether. The ether is paused
■successively through a small pledget of cotton into a beaker, and
finally the neck of the separator and stem of the funnel is washed
with ether 5 cc. as in the method above. The ether is allowed to
evaporate in a warm place, and the residue dried at 95 to 98 degrees
as long as further loss is noted.
The comparative results obtained with these methods are given
below; these show, as was to be expected, that method b yields
higher results.
Method a. Method b.
Specimen 1. 2.43 2.51
2.38 2.55
2.37 2.57
2.51
'2.51
average 2.39 per cent. average 2.53 per cent.
Specimen 2. 2.31 2.59
2.34 2.60
Method a. Method b.
Specimen 3. 1.87 2.03
1.85 2.05
1.84 2.06
Specimen 4. 1.67 1.89
1.76 1.83
1.75 1.78
1.82
1.78
1.84
Specimen 5. 1.65 1.83
1.68 1.80
Specimen 6. 1.17 1.23
1.19 1.2!)
Temperature used to dry hydrastine. It will be noted that in
the interpretation of the official method the alkaloidal residue is
directed to be dried in an oven at 95 to 98 degrees. The official
assay method for the drug directs that the alkaloidal residue be
"dried to a constant weight at 100 degrees 0," but for the fluid-
extract it is directed that the residue be dried "to a constant weight,
on a water bath." Experiments were made which showed that the
final weight of alkaloid obtained is the same whether it is dried on
a water bath or in an oven at 95 to 100 degrees. Since drying on
a water bath consumed much time — during damp days, as much
as 24 hours is required at times — I believe, that a modification of
the official method to this extent is justified, since the final result
thereby will not be altered. It has been claimed by some that in
the carrying out of official directions the exact method laid down
must be followed to the letter; but I am of the opinion that a
modification such as the one indicated above, which does not affect
the results of the method, is justified. Especially so, when the
directions for drying one and the same alkaloid differ in the assay
of the drug and its fluidextracts and are so evidently without
reason.
The extraction of hydrastine from solutions containing glycerin.
Gordin recently reported2 that the abstraction of morphine from
» Proc. A. Ph. A.. 1906, vol. p. 374.
solutions containing glycerine by means of immiscible solvents was

difficult or impractical. Desiring to know the amount of hydrastine
in liquids containing rather large and variable amounts of glycerin,
experiments were made to determine whether or not the presence of
glycerin, would, on the one hand, prevent the removal of the alka"
loid from such a liquid by means of ether and also whether the
glycerin dissolved by the ether would cause incorrect results. The
following experiments made on a solution of hydrastine' chloride
indicate that fairly correct results may be obtained, these being
but slightly in excess of the theoretical results.
a. 10 cc. of a hydrastine chloride solution, diluted with water,
15 cc., were made alkaline with ammonia water 0.1 cc. and extracted
with ether, 20, 20 and 20 cc. When the ether was evaporated in a
warm place and the residue dried at 95—98 degrees as long as a
decrease in weight was noted, 0.0875 and 0.0877 cm. alkaloidal
residue was obtained.
b. 5 cc. of the hydrastine chloride solution mixed with water,
20 cc., and treated as in a, yielded 0.0442 and 0.0441 cc. alkaloidal
residue.
c. 10 cc. of the hydrastine chloride solution mixed with glycerin
5 cc. and water 10 cc. and treated as in a, gave 0.0889 gm. and
0.0883. gm. alkaloidal residue.
d. 5 cc. of the hydrastine chloride solution mixed with glycerin
5 cc. and water 15 cc. gave 0.0452 and 0.0447 gm. alkaloidal
residue.
e. 2 cc. of the hydrastine chloride solution mixed with glycerin
5 cc., water 10 cc. and treated as in a, yielded 0.0187 and 0.0182
gm. alkaloidal residue.
The residue obtained in c, d, e, required long continued drying,
eight hours or more, before they ceased to lose weight. The second
figures in c, d, e, were obtained by evaporatiag the ether at a some
what higher temperature than in the experiment yielding the first
results.
The assay of bydrastis. For the valuation of leaf drugs,
especially henbane, belladonna and strammonium, I have advocated
(Pharmaceutical Review, 1898, vol. 16, page 180, Pharmaceutical
Review, 1902, vol. 20, page 457, Proceedings A. Ph. A., 1899, vol.
47, page 287) a modification of the Keller method of assay which
avoids the use of aliquot parts of the etheral solution containing
the alkaloids. This modification has been adopted in the Eighth

Revision of the U. S. Pharmacopeia for belladonna leaves, belladonna
root, coca, hyoscyamus, scopola and strammonium. Originally,
the modification was proposed only for drugs of which it is necessary
to use relatively large amounts for each assay and where error due
to the use of aliquot parts appeared to become appreciable. Gradu
ally, however, I have come to give it preference for drugs in genera)
over the original method, because it avoided the use of measuring
apparatus and eliminated the error liable to be introduced whenever
a volatile liquid is measured.
Below are given the results obtained in the assay of Hydrastis
by the official method (A) and by a modification thereof which
avoids the. use of aliquot parts (B).
The official method was interpreted as follows: 15 g'm. drug in
No. 60 powder contained in an Erlenmeyer flask were treated with
ether 150 cc. measured by means of a 50 cc. pipette. The flask was
stoppered and rotated occasionally during ten minutes, then ammonia
water 5 cc. was added and the mixture shaken frequently during
one-half hour, when water 15 cc. was added and the mixture
shaken vigorous!y. Then ether solution was decanted to a
100 cc. volumetric flask until the liquid readied the mark. The
solution was transferred to a separator and the volumetric flask
rinsed with ether, 5 cc. and this added to the contents of the
separator. The etheral solution of the alkaloids was now shaken
once vigorously (not for one minute as directed in the Phar
macopeia), with normal sulphuric acid 15 cc. The acid solution
was drawn into another separator through a pledget of cotton and
the ether further extracted with a mixture of normal sulphuric acid
5 cc. and water 5 cc. and then with water 5 cc. The united extrac
tions were rendered alkaline with ammonia water and extracted with
three portions of ether, 25, 20, 15 cc. each, using three separators.
The etheral solutions were united, evaporated at a moderate temper
ature and the residue dried at 98 to 100 degrees until it ceased to
lose in weight.
The modified assay process was carried out as follows: To 5
gram drug in No. 00 powder and contained in an Erlenmeyer flask,
50 cc. ether was added, and the mixture rotated occasionally during
ten minutes. Then ammonia water, 2 cc., was added, the mixture
shaken thoroughly and frequently during one-half hour, and then
transferred to a percolator. The percolate was received in a separa

tor and the drug extracted with a further quantity of ether, 50 cc.
The etheral liquid was extracted successively with a mixture of
dilute hydrochloric acid, 2 cc., and water, 18 cc. with a mixture of
dilute hydrochloric acid, 5 drops, and water, 10 cc., and finally with
water 10 cc. The united extractions were rendered alkaline with
ammonia water using litmus test solution as an indicator and
extracted with three portions of ether, 20 cc. each, using three
separators. The united etheral solutions were evaporated at a
moderate temperature and the residue dried at 98 to 100 degrees
until it ceased to lose in weight. The following results were ob
tained :
Method A. Method B.
S|>ecimen 1. a) 2.09 a) 2.81
b) 2.76 b) 2.79
Specimen 2. 4.48 4.47
Since in the valuation of flnidextract of hydrastis the berberine
is eliminated by precipitation as berberine iodide, while in the assay
of the drug itself the elimination of berberine is based on its insol
ubility in ether, it appeared necessary to demonstrate whether or
not the latter method rejected berberine as completely as is done in
the assay of the fluidextract. In the experiments made with the
assay method designated "B", the acid alkaloid extractions were
treated with potassium iodide to determine whether or not any
appreciable amounts of berberine had been extracted. In no case,
did the addition of potassium iodide cause precipitation. It may
therefore be concluded that the methods directed for the assay of
the drug and the fluidextract succeed equally in eliminating ber-
berine.
1.38 PHARMACEUTICAL REVIEW.
The Cultivation of Hydrastis.*
By John Uri Lloyd.
In Drugs and Medicines of North America, we called attention

to the fact that, in time Hydrastis, as a wild drug, would become
extinct. From eight cents per pound, at that date, the price has
reached more than f 1.00 (almost f2.00) per pound, and unless the
cultivated drug becomes a factor, even higher figures bid fair to be
maintained in the near future. As a matter of record, we will say
that about 1870 we knew a lot of 15,000 pounds of dry Hydrastis
refused in Cincinnati at eight cents per pound. We reproduce as
follows, a part of our remarks, in 1884, on this subject:
"The Past and Present Supply: — Only a small area of
country can yield the drug in' amount sufficient to repay collection
at present prices, and of this section of country, but a limited por
tion actually contributes any of it to the market. It does not
necessarily follow, however, that the plant will not disappear in
sections where it now grows abundantly but which have never yielded
the drug to commerce. Hydrastis is so sensitive to climatic influence
that even a partial destruction of the timber causes it to shrink
away, and one turn of the soil by the plow .blots it from existence.
If it were like Podophyllum, content to thrive in woodland pasture,
the future would be brighter; as it is, each year witnesses a shrink
age in area and a loss to the world (without economic return) -of
this peculiarly interesting American plant. Hydrastis has nearly
vanished from the rich hillsides bordering the Ohio river, and is no
longer found in the populated sections of our valley." — Drugs and
Medicines of North America. 1884.
• ThfH contribution may be considered in the line of a supplement to Drugs

tuid Medicines of North America, 1HS4. The information extended herein will be of
interest to those now thinking of the cultivation of the fast disappearing wild
drugs of America.
How well this prophecy has been fulfilled is evidenced by the

Hydrastis famine that now prevails.
Cultivation: — Contrary to the usual opinion, Hydrastis is
easily cultivated. It needs be kept free from grass, which smothers
it, and prevents increase by adventitious buds on the running fibers.
For this reason, rather
than the necessity of deep
shade, natural patches
of Hydrastis abound
only in ricii, soft, loamy
woodlands.
Persons familiar with
natural Hydrastis know
that it grows thick in
woodland clumps, the
patches under the beeches
where it luxuriates to
best advantage, edging
outward, and spreading
to considerable size. We
were perplexed thereby,
because we could not
Fig. 1.
accept that this in
(A Bhowa buil on rootlet.)
crease in extent and in
compactness came from the seed, which
is not abundant, and when ripe is deci
mated by being eaten by birds and
squirrels. Nor does the rhizome divide
itself. Experiments intituted in our
Kentucky woodlands and in cold frames
at our home, show that some of the
fibers creep close under the surface of
the earth, and throw up adventitious
Fig. 2.
buds (Fig. 1) which become new plants
(Bud on rootlet, fully developed.)
(Fig. 2). These fibers often shoot off to
great length, two or three feet if the soil is soft, following locations
of least resistance, and (Fig. 3) may even cast up more than one
bud. Thus the patch thickens and spreads, regardless of seed, which
when dropped by birds, or otherwise scattered, serve rather as a
nucleus for new patches in new locations, than as multipliers in old

ones.
If a rhizome be sliced
transversely into parts car
rying buds, these will sprout
and increase to a full-grown
rhizome (Fig. 4). They send
out tendrils, producing buds
that thicken the patch rap
idly, if the plant be in rich
loam, free from grass. Un
der such conditions the
plant thrives readily, and
we see no reason why
Hydrastis should not be
easily cultivated, and prove
a profitable crop after the
few years necessary to its
establishment. But it is a
delusion to look to seeds Fig. *.
Fig. 3.
as the multipliers. Cuttings
(Young rhizome A, on root (Cutting of Hy
let, two buds (B anil C) Bet and adventitious buds on drastis. P.hl-
on sumo rootlet. Rootler. zome sending
shortened in cut from 18 the fibers must be the up stalk from
inches long in order to show eye.)
buds. ) method of propagation.
Plant Pigments.*
By I. W. Brandel.
O bserver. flower. t&lc. BOl. residue.
Ranunculace.e.
Aq uilegia vulga ris* Hu nefeld
Aquilegia speciosa8
Anemone hortensis9 Filhol red
Anemone pavoninai0 Filhol red
Delphinium hybridum Brandel blue colorless
Delphinium 1i Elsner red colorless blue
Delphinium discolor 12 H unefeld pale red
Delphinium consolida 13 Perkin blue
" " ...... Vogel blue
" Vogel blue
Delphinium formosumi* Vogel blue
Vogel blue
Delphinium zalil10 Perkin yellow
Clema tis in tegrifolia 7 H u nefeld
8 H unefeld
Xigella damascenu 5 Vogel blue
Rosace.e.
Crataegus oxyca nthai1 Perk in white
" " 18 Wittstein white •
Potentilla formosa19 Eisner red colorless red
Potentilla reptans23 Vogel yellow
Pyrus communis 18 Wittstein
Rosa odorata Brandel dark red colorless purple
Hybrid Tea rose Brandel pink yellow brown
Bourbon rose 'Hernosa' Brandel pink colorless red
• Continued from page 12.1.
» Journ. pr. Chem. 9, p. 217.
» Turned blue by ammonia (Compt. rend. 81), p. 196).
i» ContainH two pigments (Compt. rend. 50. p. 11831.
11 Yellow prec. with lead acetate (Chem. Centralbl. 8, p. 570).
'» Contains iron (Journ. pr. Chem. 16, p. 84).
t» Contains glucoBlde of kampherol (Journ. Chem. Soc. 81. p. 585).
i* Turned green bv ammonia (Sltzb. d. Acad. Muenchen, 1870. I, p. 17).
1« Has very faint acid r action (Sltzb. d. Acad. Muenchen, 1879, p. 19).
!• Contains glucosldes of Isorhamnetln, quercetln and a third coloring matter
(Journ. Chem. Soc. 78, p. 267).
i» Contains quercetln as glucoslde (Chem. News 74. p. 278).
is Contains propylamine (Ann. d. Chem. 91. p. 121).
i» Solution gives vellow prec. with lead acetate and yellowish-red prec. with
line chioride (Chem. Centralbl. 8, p. 572).
»o Same as i».
142 PHA KMACE UTICA L RE VIEW.
Color ot Color of Color ol
Observer. flower, ale. sol. residue.
ROSACE.e.
Rosa cianamomna*0 Elsner red colorless red
Rosa centifolia 21 Hunefeld
" " *• Vogel white
" 2* Vogel red
" 22 Vof'el yellow
Rosa gallica20 Elsner red colorless red
" 21 Hunefeld
" " 20 Senier red colorless
Spirea ulmaria23 Vogel white yellow
Spirea ulmaria20 Loewig yellow yellow
20 Buchner
Spireu fllipendula*7 Filhol white
Spiivn opulifolia, Ij.2* Ludwig
Rubiace.e.
Gallium mollugo20 Filhol white
Gallium vervm a0 Vogel yellow
RUTACE.E:
Citrus decumara3i Hoffman
Murraya exotica 32 Hoffman
Saimnuace.e.
Aesculus hippocastanam a8 ...Rochleder yellow yellow
" " 34... Stein yellow yellow
as...Hlasiwetz
Aesculus paviaa* Stein red red
Acer pseudo-platanus 3,1 Stein
SaXIFRAGACEjE.
Hortensia speciosa m Schnebler
Hydrangea quercifolia 3* Marquart yellow
Philadelphus coronariasu Filhol white
3i Contains iron (Joarn. pr. Chem. 16, p. 84).

M Contains quern'tin also a red crystalline pigment (Ph. Journ. 8(1. p. 650).
»• Solution has acid reaction (Sltzb. d. Acad. Mtiei chen, 187!), p. IB).
2* Solution has strong acid reaction (Sltzb. d. Acad. Muenchen, 1871*. p. 19).
23 Contains a crystalline substance called spirilla (.1. pr. Chem. 19, p. 286).
2t> lluils contain sallcln and flowers contain salicylic aldehyde (Buchner's Ann.
88. 27p Compt.
224 ). rend. 39. |). I1*4.
2s Bot Centralbl. 21, p. 4t.
20 Compt. rend. Hl), p. 195.
»« Alcoholic s ilutlon has acid reaction (Slt«t>. d. Acad. Muenchen, 1879, p. HI),
si Contains glucoside narlngin (Ber. 9. p. (190).
52 Contains glucoside murrayin (Ber. 9, p. 690).
33 Buds are colorless, contain quercetin glucoside (Cheui. Centralbl. Ho, p. 166).
s* Contains para-carthamln (Journ. pr. Chem. 89, p. 41)5).
3S Contains quercetin (Ann. d Chem. 112. p. 90 1.
3« Contains ruM'i which yields quercetin (Journ. pr. Chem. 85, p. 851.)
37 Flower is ordinarily red htit can be changed to blue by introducing carbon,
iron or aluminum into the soil (Journ. pr. Chem. 1. p. 46;.
»s Flowers change to red upon fading (Arch, d t'harm. 5(1. p. 262i.
39 Turned yellow by ammonia (Compt. rend. 89, p. 194).
Scitamine.e.
('anna (Goldeu Beauty) Brandel yellow brown brown
" (Yellow Seedling) Brandel yellow yellow
" (!'res. Cleveland) Brandel dark red brown brown
" (C. 0. Quintus) Brandel yellow yellow yellow
" (The Rival) Brandel yellow slightly yellow yellow
Canna Hmba tn 40 Marquart
C'auna indica*i Eisner violet partly decolor, violet
ScHOPHCLAKIACE.E.
Antirrhinum majus Brandel red brown dark red
" " Brandel purple colorless brown
" " Brandel yellow brown brown
" " Brandel .yellow yellow yellow
Antirrhinum majus*'2 Vogel red
" •' 43 Schnetzler red
Calceolaria rugos** Vogel yellow
Digitalis purpurea 4r> Elsner red partly decolor, red
49 Vogel red
" *s Vogel white
*i Vogel red
Linaria vulgaris** Riegel yellow
Linaria oymbalaria*i> Vogel violet
Pentstemon diffusum5" Marquart white
Veronica spica ta 5i Hunefeld
Veronica triphyllos^2 Vogel blue
Veronica chamaedrys53 Vo;'el blue
Veronica agrestis52 Vogel blue
Verhascum nigrum*0 Vogel yellow
Verbascum thapsuss3 Hunefeld
Solancea.e.
Fabiana indica5* Filhol yellow
Lycium barbarum5S Vogel red
Nicotiana virginiana5* Vogel red
Petuna hybrida5n Vogel violet
*o Contains red and yellow pigment (Arch. d. Pharm. fi(5, p. 257).
*t Aqueous solution gives a blue-green precipitate with lead acetate (Chem.
(Vntralhi. », p. 570).
« Turned blue by ammonia (SItzb. d. Acad. Muenchen, 1870, I, p. 17).
*3 Forms colorless solution with borax solution (Jahresb. u. d. Fortschr. d.
Chem. 1877, p. 925).
Not changed by ammonia (Sltzb. d. Acad. Muenchen, 1870, I, p. 17).
*» Solution gives yellow prec. with lead acetate (Chem. Centrnlbl. 8, p. 570).
*» Contains iron i .1 o urn. pr. Chem. 10, p. 84).
*t Alcoholic solutioa has strong acid reaction (Sitzb. d. Acad. Muenchen, 1S79,
p. 1!)).
*» I'sed as dyestuff (Chem. Centralbl. 14. p. 454).
*» Solution has acid reaction (.SItzb. d. Acad Muenchen. 1 H7!t. p. 19).
so Becomes red upon failing (Aich. d. Pharm. 56, p. 2(>H).
si .Tourn. pr. Chem. 9, p. 217).
5a Solution bus faint acid reaction (SItzb. d. Acad. Muenchen, 1879, p. 19).
5' Contains iron (.Tourn. pr. Cbelu. 16, p. 84).
5* Compt. rend. 50, p. 1182.
55 Aqueous solution has strong acid reaction (Sltzb. d. Acad. Muenchen, 1S7!),
p. 19).
5« Turned green by ammonia (Sltsb. d. Acad. Muenchen, 1870, 1, p. 17).
SOLANCE.e.
Physalis alkekenki57 Vogel red
Solanum dulcamara** Yogel violet
Ternstroemiace.e.
Camel'm species 89 Filhol red
Camelia japonica00 Hunefeld
Thymelaeace.e.
Daphne mezereum0i Rochleder rose
Imhellifer.e.
Coriandrnm sativum 82 '. Vogel white
Verhenace.b.
Lantana delicatissimum Brandel lilac colorless pink
Lantana camara Brandel yellow yellow yellow
Verbena tenera maonetti Brandel blue colorless blue
Verbena (red) Brandel red slightly pink purple-red
Verbena bybrida 1,3 Vogel red
" " °* Vogel blue
Verbena officinalis03 Vogel rei 1
Vioi.ace.e.
Viola (Violets) Brandel blue colorless blue
Viola tricolor07' Marquart yellow
" " «a Eisner red colorless red
" « Hunefeld yellow
" «s Vogel blue
Viola tricolor Brandel purple pink purple
Viola tricolor maxima00 Vogel blue
Viola maxima 10 Vogel yellow
Viola corn uta 08 Vogel blue
Ho/a odorata71 Macaire blue
™ Hunefeld blue
" Not changed by ammonia (Sltzb. d. Acad. Muenchen, 1870. I, p. 17>.
Alcoholic solution had faint acid reaction (Sltib. d. Acad. Muenchen, 1879,
p. 19).
s» Turned blue by acids (Compt. rend. 50, p. 545).
«o Journ. pr. Chem. 10. p. 69.
'•' Contains glucoslde daphnine which yields daphnetlne (Journ. pr. Chem. 90,
p. 442).
«» Turned yellow by ammonia
has strong(Sltzb. d. Acad. (Sltzb.
Muenchen, 1870.Muenchen,
I. p. 17).1870
d* Alcoholic solution acid reaction d. Acad.
p. 19).
" Alcoholic solution has neutral reaction (Sltzb. d. Acad. Muenchen, 1879,
p. 19).
«» Arch. <I. Pharm. 56, p. 257.
«« Solution gives dark green prec. with lead acetate and violet with line
chioride (Cnem Centralbl. 3, p. 572).
«7 Forms yellow solution with oil of turpentine (Journ. pr. Chem. 16, p. 68;
9,. p. 217).
Alcoholic solution has faint acid reaction (Sltzb. d. Acad. Muenchen, 1879,
p. 19).
«» Alcoholic solution has neutral reaction I Sltzb. d. Acad. Muenchen, 1879,
p. 19).
'o Not changed by nmmonia (Sltzb. d. Acad. Muenchen. 1870, I, p. 17).
" Turned green with alkalies and red with acids (Ann. de Chim. [2] 38, p. 415).
" Journ. pr. Chem. 9, p. 217.
Theories of Plant Pigmentation. The study of the pig

ments in the colored organs of plants, very early attracted the
attention of chemists as well as of botanists. Virey1 in 1811
attempted to show that the colors in different plants were dependent
on their medicinal properties.
On account of the great predominance of green in the vegetable
kingdom, it was but natural that the early investigators should
consider the other plant pigments as related to the green pigment,
first called chlorophyll by Pelletier." This point of view was empha
sized by the recognized importance of the chlorophyll to the life of
every plant, and by the study of the deportment of chlorophyll to
wards light, heat and chemical reagents. That chlorophyll is a
a mixture of substances of different colors was first shown by
Mueller3 who noticed that upon evaporating an alcoholic solution
of chlorophyll, a series of colored rings were formed. The outer ring
was yellow, then followed a bluish ring and finally the green.
Mueller therefore argued the existence of three pigments in chloro
phyll. According to Hartsen*, 1872, the yellow pigment can be ob
tained in a crystalline form. This substance he called chrysophyll.
By shaking an alcoholic solution of chlorophyll with benzene, Kraus5
obtained a golden-yellow substance which he called xanthophyll and
a blue-green substance which he culled cyanophyll. The mixture of
these two pigments again produced the green chlorophyll.
By shaking chlorophyll with a mixture of ether and hydrochloric
acid, Fremy6, 1860, obtained a yellow ethereal layer and a blue
acid layer. The chlorophyll, therefore, according to his ideas con
sisted of two pigment* — a yellow, called phylloxanthine and a blue,
called phyllocyanine — in variable proportions. The phyllocyanine
was regarded as being present in the form of a potassium salt, be
cause of the large quantity of potassium chloride which separated
from the hydrochloric acid solution.
Most authors agreed that the blue pigment of chlorophyll readily
underwent changes, and it was to this pigment that they most often
looked for the source of other pigments. The yellow color of fall
leaves is explained by Fremy7 by assuming the complete decomposi-
l Journ. de Pharm., 3. p. 529.
» Jatirb. f. wIbB. Bot. 7, p. 2O0.
« Chem. Ceutrnlbl . 1872. p. .125: 1875, p. 013.
e Compt rend , 50, p. 4(15: 68, p. 188.
» Compt. rend., 50, p. 405.
tion of the blue phyllocyanine, the leaf being then colored only by
the yellow pigment. The presence of this pigment in variable quan
tities would produce different shades of yellow. Besides undergoing
complete decomposition during the life process of the plant, the blue
pigment was thought to be able to undergo such changes as would
result in the formation of a new pigment. Thus according to Kraus,8
1872, the brown coloration in leaves is caused by a peculiar modifi
cation of this blue constituent of chlorophyll; and, according to
Haberlandt,9 1876, this modification can be brought about only by
the frost. Both authors agree that a red pigment called anthocyan
is also produced from the blue constituent of chlorophyll. By
treating chlorophyll with dilute potassium hydroxide, Hardsell10
obtained a purple pigment which he called purpurophyll, and which
he mentions as a possible pigment of blue flowers. Hoppe-Seyler11
in 1879 isolated two crystalline substances from the chlorophyll of
grass, a red substance identical with Bougarel's erythrophyll which
was found in the leaves of sycamore and peach12; and a yellow
substance to which he gave the name chlorophyllan.
In the same way as chlorophyll could produce such a variety of
pigments closely related to and still associated with chlorophyll itself
in leaves, so by more radical and complete changes the pigments of
the flowers were produced.
This argument seemed the more reasonable because of the fact
that flower buds are green.
According to Marquart,13 1836, the color of all flowers is due
to one of two pigments, derived from chlorophyll, or sometimes to
both pigments. One of these two fundamental pigments is yellow,
the other blue. The yellow pigment was called anthoxanthin and is
the substance which gives its color to all yellow flowers. The blue
pigment is called anthocyan and is the pigment found in all blue
and violet flowers. The pigment in red flowers is the blue anthocyan
colored red by acids formed during the life process of the plant. The
author claims that the aqueous solutions of all red flower pigments
are acid in reaction. Upon very careful neutralization, the blue
anthocyan can be obtnined. On the other hand, solutions of blue
» Bot. Ztg., 30. pp. 109. 127. 558, 508.
• Chem. CentralM., 47, p. 357.
io Poks. Ann., 140. p. 158.
>i Ber. 12, p. 1555.
u null. Soc. Chim., 27, p. 442.
>» Arch. d. Pharm., 56, p. 244.
anthocyan become red upon the addition of acids. White flowers

owe their color to a substance called "Blumenharz" which is con
sidered to be an intermediate product in the changeing of chlorophyll
to anthocyan. In the buds all flowers are green. If the chlorophyll
takes up water or the elements thereof, anthoxanthin is formed and
the flower becomes yellow. The green buds of white flowers, become
white by the abstraction of water from chlorophyll and if this ab
straction of water be continued the blue anthocyan is formed.
According to the author, white flowers can be changed to red by
treating them with a dehydrating agent like sulphuric acid. Whether
the flower becomes blue or red is determined by the following con
ditions. If only carbonic acid be present in the bud, this is breathed
out as the bud opens and the flower becomes blue. It is because
they are not able to breath out the carbon dioxide that the buds
of even blue flowers are red. If, however, a fixed acid be present in
the bud, the flower becomes red. All intermediate colors are due to
various admixtures of anthoxanthin, anthocyan and chlorophyll.
Schuebler14 in 1827, attempted to show the relation of the
various plant pigments other than green to each other and to
chlorophyll. He devided all pigments into two groups, the yellow-
red group and the blue-red group. Between these two, was the
chlorophyll. The yellow-red group contains the pigments produced
by various degrees of oxidation of the chlorophyll, while the pig
ments of the blue-red group represented various stages of deoxidation
of chlorophyll. It is not clear from his article upon what he based
this assumption nor does he try to explain how this oxidation and
deoxidation is brought about in the plant. His arrangement of
colors is shown in the following table:
■ Oxidation
Chlorophyll
Blue-green
Blue
Blue-violet Deoxidation
Violet-red
Red
i* Arch. d. Pharm., 20, p. 262.
Chlorophyll, therefore, is the basal substance of all pigments

changeing on the one hand to oxidized pigments and on the other
hand to the deoxidized pigments. This was in harmony with the
fact that both yellow and blue flower pigments could be changed
into red. That the two reds thus obtained were different substances
is shown by the fact that the red obtained from blue flowers, could
be changed back to blue by the addition of dilute alkali, while the
red pigment resulting from yellow flowers could not be changed to
blue by means of alkali. The flowers colored red naturally could
also be devided into two classes accordiny to their behavior toward
caustic alkali.
In opposition to this, Elsner,15 1832, as well as others held that
all red flowers contained the same red pigment, because of the
similarity of their behavior toward chemical reagents and that the
red coloring matter in leaves and fruits is also identical with that
from red flowers.
However, the majority of persons who worked on plant pigments,
did not venture to explain the relation of these pigments to chloro
phyll hut were satisfied with the general statement that all flower
pigments are due to slight changes produced in the chlorophyll by
acids or alkalies.1"
In Nome instances a special change was attributed to the chloro
phyll which was characteristic of an individual plant. Thus Witt-
stein17 examined the red pigment in the leaves of Vitis hederacea.
This pigment, he called cissotannic acid, C20H12O16. and regarded
it as a decomposition product of chlorophyll. This cissotannic acid
is supposed to exist in the plant as the ammonium salt, the
ammonia coming from the nitrogen of the chlorophyll.
In order to explain the formation of the greeii chlorophyll as
well as other pigments in a plant, Macair-Princep,18 1828, assumed
the presence of a fundamental substance underlying all plant pig
ments which he called "chromul." This is assumed to be an almost
colorless substance which by the action of alkalies is changed to
green chlorophyll. This in turn is changed to yellow and then to
red by the action of oxidizing agents or acids. Thus a green leaf
in contact with acids becomes yellow, the green being restored by
is Chem. Centralhl.. 8, p. 067.
i« Bot. Centralbl.. 5, p. 10U.
t7 Jnhresb. u. d. Fortwhr. d. Chem.. 0, p. 504.
is Ann. d. Chim. (2), 38, p. 415.
the addition of alkali. A yellow autumn leaf when placed in a

solution of a caustic alkali again becomes green. The fall coloration
of leaves is, therefore, regarded as being due to the absorption of
larger quantities of oxygen. The "chromul" is also the funda-
nmetal pigment substance in flowers, for red flowers when treated
with alkali become green. Blue flowers obtain their color by the
union of the red "chromul" with plant alkalies or alkaloids. For
this reason some red flowers become blue when brought in contact
with quinine.
According to Berzplius19, 1837, the assumption of a fundamental
substance, like Macaire-Princep's "ehromul", is entirely unfounded.
He claims that it is impossible to change a green leaf to yellow or
red by means of acids and back again to green by means of alkalies.
That some red pigments become green when treated with alkalies, is
not due to the formation of leafgreen but to the formation of a
compound of the red pigment with the alkali.
In 1837, Hoppe20 regarded the "chromul" of Macaire-Princep as
the fundamental substance which produced chlorophyll or green
plant pigments only. In other colored parts of a plant he assumed
the presence of an entirely different basal substance or rather a
mixture which he called chromogen. This was a colorless substance
consisting of two compounds, viz. erythrogen and xanthogen. The
former of these, by the action of acids, forms the red plant pigments!
and the latter, by the action of alkalies, forms the yellow pigments.
White flowers contain unchanged colorless xanthogen because white
flowers become yellow by the action of alkalies. Yellow flowers con
tain only xanthogen while blue and red flowers contain both
erythrogen and xanthogen. Slight variations in color are due to
compounds of erythrogen and xanthogen with other vegetable
principles.
Instead of assuming the presence of one basal substance Virey21
in 1838 also referred plant coloring matters to two basal substances,
a yellow pigment and a blue pigment. Chlorophyll was a union of
these two pigments. This agreed with the accepted notion that
chlorophyll consisted of a blue and a yellow pigment. Red flowers
contained the blue basal pigment which was turned red due to the
development of some acid principle in the plant, and not infrequently
i» Pog(f. Ann., 42, p. 422.
»" Jonrn. f. prakt. Ghem., 10, p. 269.
« Journ. de Pharm., a0. p. BUI.
yellow flowers turn red. Upon fading the color of flowers always
goes back to their primitive basal color. Thus the red rose turns
yellow, the red hortensia upon drying turns blue. White flowers
upon fading turn either yellow or blue. The terms xanthine and
cyanine first applied by Decandolle22 to plant pigments were used
by Virey to designate his yellow and blue basal pigments respectively.
Virey objected to regarding the yellow pigments as oxidized deriva
tives of chlorophyll and the blue pigments as deoxidized pigments,
because many blue flowers are white or red in the bud, becoming
blue as the petals come in contact with the air. Therefore, blue
pigments can not be the result of deoxidation. Virey attributed the
differences in color of flowers, to differences in the composition of
the plant juices or to differences in the composition of the soil, in
which the plants grow. The color of a flower very largely depends
also upon whether the plant blooms in early spring, in summer or
in fall. Although flowers of every color bloom at any one time,
there are more white and blue flowers in the spring time, more red
in the summer, and yellow predominates in the fall.
The color of flowers, as affected by the composition of the soil,
referred to by Virey, had already been given as an explanation for
changes in color by Schuebler and Lachenmeyer23 in 1834. They
found that the presence of considerable quantities of carbon and
ferrous oxide in the soil changed the red hortensia to blue. The
authors explain this by saying that soils containing a considerable
quantity of these easily oxidized substances are in a deoxidized con
dition. In the absence of these substances, the oxygen would be
used to oxidize stronger acid-forming substances and then the flowers
would bloom red. On this same basis of increasing or decreasing
deoxidation, as the plant and fruit developes, the color of the ripened
fruit is explained. Unripe green fruits turn yellow, then red and
finally blue. Unripe fruits containing. a large quantity of acids upon
ripening turn only to red. If the quantity of acid diminishes greatly
upon ripening the fruit assumes a bluish color as in the case of
grapes.
»» Journ. f. prukt. Chem., 1, p. 46.
(7b he continued?)
Phytochemistry in America.t
Helen Cecilia DeSilver Abbott was born in Philadelphia

Decemher 23, 18">7. Her early education seems to have been entirely
under the direction of private teachers. The winter of 1878—'79
she spent in Paris studying music, also the season of 1880—"81.
Having become interested in physics, she entered the Womans Medical
College at Philadelphia, where she began the study of chemistry.
Her chemical studies were supple
mented during the long summer
vacations by work done in Pro-
essor Trimble's laboratory at the
Philadelphia College of Pharmacy.
In 1*85 she dropped the medical
course in order to pursue more
general studies looking toward
admission to the University of
Pennsylvania. At the same time
she prepared several public lec
tures on plant chemistry delivered
at Philadelphia and Washington.
In 1887 she again went to Europe
in search of a laboratory in which
to pursue her phytochemical
studies, but upon her return she
entered Tufft 's College and worked
under the direction of Professor
Arthur Michael to whom she was
married in June 1888. Both
then started on a trip around the
world which lasted about a year and a half. After a brief residence
at Worcester they took up their residence at Bonchurch, Isle of
Wright, England, in 1891, where they equipped a private laboratory.
During their residence here of four years she published several reports
as joint work with John Jeanpretre. Upon their return to the
United States, she delivered another public lecture in I8i>."i, and
resumed medical studies at Tuffts. The year 18!)<i found her abroad
• Contribute<! from the Seminary in Plant Chemlstry at the University of Wls-
conxln by ,VW//« A. Wakemaa. > r
PllARMACEUTICAL REVIEW.
again, but this time interested in sociological topics. In 1903 she

graduated from Tuffts as M. D, whereupon she began the practice
of medicine. She died in Boston, November 29th, 1904.
Her phytochemical work readily falls into three groups, each
group representing fairly well a corresponding period of activity:
I.—Phytochemical investigations carried on under the direction"
of Professor Trimble.
1884— Preliminary analysis of the bark of Fouquiera splendens. (Read
at the Phila. meeting of the A. A. A. S.) Am. Jouru. Ph., 57,
p. 81.
1885—Chemical study of Yucca an/rmtifnlia. (Read at the Ann Arbor
meeting of the A. A. A. S.) Am. Journ. Ph., , p. .
1886—On haematoxvlin in the burk of Saraca imlica. Proc. Ac. Nat.
Sc. of Phila., 38, p. 352.
1888—On the occurrence of solid hydrocarbons in plants. Am. Journ. of
Pharm., 6O, p. 321.
II.—General papers read at Buffalo, Philadelphia and Washington.
1880—Certain chemical constituents of plants considered in relation to
their morphology and evolution'. (Read at the Buffalo meeting
of the A. A. 8 ) B)t flaz.. II. p. 270.
1887—Plant analysis as an applied science. Journ. Franklin Inst.,
124 ii, p. 1. (Also issued as a pamphlet.)
Plant chemistry, as illustrated in the production of sugar from
sorghum. Proc. Alumni Assn. Phila. Coll. Pharm. (Also issued
as pamphlet, Burk & McKetridge, Phila., 1887.)
The chemical basis of plant forms. Journ. Franklin Inst., 124 u,
p. 101. (Also issued as Pamphlet, Phila., 1887.)
Comparative chemistry of higher and lower plants. Am. Natura
list, 31, pp. 719 & 800. (Also issued as pamphlet, Phila., 1887.)
1895—A review of recent work in the class of carbohydrates. Journ.
Franklin Inst.. 141 n (90), p. 217. (Also issued as pamphlet,
Phila , 1896.)
HI.—Reports of joint work with John Jeanpretre done in the
Isle of Wright.
1892—Ueber eine neue Bildungsweise von aromatischeu Nitrilen. Ber.
d. d. ch. lies.. 25, p. 1615.
Zur Kenntniss der Mandelsaure und ihres Nitrils. Ibidem, 25,
p. 1078.
Zur Kenntniss der Addition von Brom und Chlor zu fester Croton-
sfture. Journ. f. pr. ('hem., 40, p. 273.
1894—Zur Constitution des Phloretius. Berichte, 27, p. 2080.
For an appreciation of ber work and a complete reprint of all
she has published see "Studies in plant and organic chemistry, and
literary papers by Helen Abbott Michael (Helen C. De S. Abbott)
with biographical sketch.'' One vol., pp. 423, with portrait. The
Riverside Press, Cambridge, Mass., 1907.
The Apothecary. A Literary Study.
By Eilward Kremers.
2. Dtt Mein Jena.

Although stud, plmrm. Korff is but a minor character in the
story that tnkes its course between the two covers of "Du mein
Jena," he is of interest not only to the student of the pharmacist
in literature, but also to the general reader. This particular interest
he acquires because he is utilized successfully by the author as a
representative of the small "unstudent-like" class of students. As
such he is deserving of a closer inspection. In order that we
may understand him in the role which he plays, it will be necessary
to ascertain first of all how his training as an apothecary placed
him into this category ; how he acts while a student at the Univer
sity; and lastly, what is the attitude of other students toward him.
Although only in his third semester (p. 157) he is decidedly one
of the older students, having matriculated at the age of twenty-
seven. It had been necessary for him to work many years in an
apothecary shop in order that he might earn the money needed for
his university studies.
A capable man, he had nevertheless become thoroughly embittered
because of poverty at home and an unhappy youth. Avoiding the
company of others, he had eagerly devoured everything written on
the social questions of our own times. The practical life he had
led had widened his horizon greatly, and he possessed a better
comprehension of the problems of the day than most of his fellow
students.
That a person of Korff's age, experience in life, and wider
sympathies could not find congenial company, particularly among
the younger members of a student fraternity, is but natural. His
membership in the Landsmannschaft Alemannia, though decidedly a
democratic society when compared with that of the Corps Vandalia,
therefore calls for an explanation.
His affiliation with the students of the Alemannia was due to

peculiar circumstances. The director of the Pharmaceutical Institute,
Dr. Mautz, who was an "alter Herr" of the Alemannen, had "rushed"
him, and Korff had finally allowed himself to be persuaded because
he foresaw the possibility of an assistantship which might realize him
several hundred marks per year. This expectation was realized, but
it did not make closer his relationship to the Alemannen.
As a man of experience in life, he did not possess that narrow
fraternity spirit which characterizes so many of the fraternity
students, be they members of a "Corps," "Burschenschaft" or
"Landsmannschaft." This is brought out in the scene that intro
duces him into the story. It is the one at the Kneipe of the Ale
mannen, which, for the sake of economy, is also open to public
guests. An extra political election having become necessary, the
students have allowed themselves to be dragged into a discussion
with the citizens. In it Korff sides with the citizens who, though
themselves not social-democrats, are going to vote for the candidate
of this party because their only other choice is the candidate of the
feudal agrarians.
That a man of his age, experience in life and sympathies should
prefer to attend a political meeting of the social-democrats rather
than join his younger brethren in a sleighing party, seems but
natural; that, when provoked by the sarcasm of some of the younger
members, he should speak of their ladies as "d amme Giinse," seems
equally natural. That a member of a fraternity who was induced ,
to join by his professor because of possible financial gain, one who
was much more interested in newspaper accounts of social and
political questions (p. 167) than in the small talk of his colleagues,
that such a person should see fit to drop out of such an organiza
tion when internal strife and dissension cause open rupture, will
surprise no impartial judge; (p. 207) neither can it surprise any
one that the partisans in this family strife should feel disgusted at
this display of disloyalty and even cowardice as it appeared to
them.
This latter statement leads us to the consideration of the last
aspect of the subject, viz.: the relation of the other students to the
stud. pharm. The student body at large at Jena does not enter
into the story, so we find ourselves restricted to the attitude of his
fraternity brethren.
That he should have been elected a member at all was, no doubt,
due in part to the Director of the Pharmaceutical Institute, who
was desirous of adding a bright student to the fraternity of which
he at one time was an nctive member, and in which he still took a

personal interest; in part, no doubt, to the fact that in a small
university like Jena the number of possible recruits for the numerous
fraternities is limited. Indeed, one of the most aristocratic Corps
hud to be "suspended" because of insufficient membership, and could
be revived only by the desertion of fully one-half of the active mem
bers of the Landsmannschaft Alemannin, i. e., by the breaking up of
another fraternity.
That the younger members, especially those with more aristo
cratic tendencies who afterward deserted their colors, had no use for
the man who preferred to read newspapers rather than listen to
their small talk, who would even consent to talk politics with the
philistines and, what was worse, take sides against the agrarian
tendencies of the young upstarts, goes without saying. It certainly
redounds to the credit of stud, phurm. Korff that the older members
of the fraternity, although they are much more enthusiastic for their
Landsmannschaft, side with him in his differences with the younger
element and particularly their leader, the present presiding officer.
It is particularly this young spendthrift, wasting his money in a
loose life and aspiring to a higher social status, who regards it a
hardship that he should count among his fraternity brethren one
who has stood "behind the counter" (p. 157). Yet this same dude
later sold out his fraternity, or such part thereof as he could
control, to the Corps Vandalia, and thus broke his oath of allegiance
to the colors of the Alemannen.
In the eyes of these young fellows who had come to Jena
primarily for the purpose of having a good time, it was "idiotic"
(p. 169) to read the parliamentary speeches of such popular leaders
as Bebel and Richter, of ministers like Bosse and Studt. They were
not interested in weighty problems of tariff or revenue. Such
"leathern" subjects were all right for senile philistines, but certainly
of no interest to the wearer of the colored cap (p. 167).
Nevertheless it was the group of older members of the Alemannia,
those who had appreciated his worth though they did not find him
sympathetic, who regarded his resignation in even a worse light
than the desertion of the younger members. While this severer con
demnation may not be fully justified, it can nevertheless be appreci
ated by the impartial judge. Whereas the younger members had
committed treason, he, in their eyes at least, had revealed some
thing worse, viz.: cowardice; for his resignation was regarded
merely as an excuse to escape the series of duels that had to follow
(pp. 207. 212, 224).
The action of stud, pharm. Korff whs exceedingly sensible, but it

was in direct opposition to that spirit of loyalty which the fraternity
was designed to foster. The reader cannot but feel that enthusiastic
Heldenrich, the principal character of the story, who lays aside all
personal considerations in order to come to the rescue of his beloved
Alemannia, is unquestionably the nobler character of the two.
Though before an impartial tribunal, Korff's reasons for his
resignation would be found valid, his disappearance from the scenes
reminds one of Goethe's delineation of the apothecary in "Hermann
and Dorothea.'* One cannot but feel that in the time of personal
danger as well as in a period of need by his fraternity, Korff dis
plays the characteristics of a selfish person.
That his early misfortunes as well as his Iater education should
have made him thus, does not alter the situation. If the class of
young men from which pharmacy recruits itself, at least in part,
should be of such character; if their training as apprentice and as
assistant should change their horizon so as to put them out of
touch with a large percentage of their colleagues who have come
directly from the gymnasium ; if their more rational view of life, in
cluding student life, deprive them of the possibility of being embued
with that enthusiasm of the student body at large, much of this is
to be regretted. It is to be regretted, even if this change of horizon
be a widening, which leads them to see the foolishness of many
student enthusiasms and the great waste of life on the part of the
students as a body.
Whatever our sentiments on these points may be, the author
has availed himself of an excellent opportunity to portray the life
of the student at a small German university when he placed this
stud, pharm. in rather striking opposition to his fellow students.
When the writer began the story, his own experiences at two German
universities caused him to think of such a possibility. The intro
duction of stud, pharm. Korff in the middle of the story, when the
somewhat monotonous descriptive style of the author began to be
displaced by the more vivid style of action, at once arrested his
attention. From a literary point of view, the solution is certainly
an excellent one. As tp the facts, one may well admit that among
the student body of German universities pharmaceutical students
with the virtues and with the shortcomings of stud, pharm. Korff
are by no means the exception.
Literary.
Books Reviewed.
Lehrbuch der gerichtliuhen Chemie mit Beriicksichtigung sanitiits-
polizeilicher und medizinisch-chemischer Untersuchungen. Zum
Gebrauche bei Vorlesungen und im Laboratorium, bearbeitet
von Dr. Georg Baumert, Professor fur Nahrungsmittelchemie
in Halle a. S. Erster Bd., pp. XVI, 490, mit 53 eingedruckten
Abbildungen. Zweite riinzlich umgearbeitete Auflage. Verlag
von Friedrich Vieweg und Sohn in Braunschweig. 1907.
M. 12.00, geb. M. 13.00.
The volume before us constitutes the first volume of the "Lehr
buch der gerichtlichen Chemie" of Baumert, Dennstedt and Voigt-
laender. Volume one covers the detection of poisons and of sub
stances, detrimental to health, in the organs of dead bodies, in
urine, in foodstuffs and beverages, in common objects of use, in
water, air and the soil. It also takes into consideration such
examinations as are demanded by revenue officers, damage done to
vegetation by smoke, and similar problems subject to the laws of
the country for which the book was primarily written. As indicated
by the above reproduction of the title page, volume one has been
rewritten by the first of the three authors.
Volume two emenates from the pens of the other two men and
is to cover the subject of imitations of handwriting, blood, sperma
and other toxicological subjects, with the special aid of photography.
It is this special treatment that has caused the publishers to issue
the second part as a separate volume.
After a brief introduction which comprises definitions of the word
poison and of the scope of toxicology or legal chemistry, volume
one is arranged into two parts: the first general, the second special
in character.
The subject matter of the general part is disposed of in three
chapters. The first deals with general rules, the preparation of a
report, the corpus delicti, the question of fees, and the general sub
ject of the dedection of poisons and the problems of toxicological

investigations. The second chapter deals in like manner with food
stuffs and beverages, objects of utility etc., such as kitchen and
other utensils, colors and colored objects, toys. The third chapter
finally deals with reagents, their special purification or preparation
for toxicological investigations, and with the apparatus and utensils
employed.
The special part consists of three subdivisions each with several
chapters. The first deals with inorganic poisons, the second with
organic poisons, and the third with the general methods for the
dedection of poisons.
In the large group of inorganic poisons, arsenic comes in for
special consideration, the numerous methods that have been proposed
for its detection being separately described and often illustrated.
In this connection the biochemical method with the aid of Penicillium
brevicaule deserves special mention as an uncommon method of
chemical analysis.
Of organic poisons the classical hydrocyanic acid and its salts is
conspicuous for the space devoted to it. Decidedly more modern is
the problem to detecting denatured alcohol that has been renatured.
The alkaloids have always played an important role in legal
chemistry. In importance, however, they have possibly been sur
passed by such substances as formalin, benzoic acid, salicylic acid
and saccharin, to say nothing about organic dyestuffs used in the
preparation of immitated and semi-natural foodstuffs.
A supplement supplies the German laws bearing on the subject
and a few minor additions, such as the detection of several new
remedies, viz. antipyrine, pyramidon, phenacetine, p-phenetidine
phenocoll and veronal. The book is further provided with two good
indices, an authors' index and a subject index.
While the contents of the book afford another example of Ger
man thoroughness, the book itself is of a kind that calls forth the
admiration of the reader. The type is clean cut, the arrangement
of the page is as "iibersichtlich" as can be asked for, and, last but
not least, the wood cuts are excellent. There is something in the
xylographic output of this firm that makes envious those who get
tired in the long run of zinc etching and half tone, no matter how
perfect t he latter may be. For the illustration of apparatus certainly
nothing surpasses an excellent wood cut. E. K.
Window Displays for Druggists comprising for the most part

engravings and descriptions of over a hundred attractive dis
plays which have been designed and used with success by
druggists throughout the country, together with some useful
suggestions on the subject of window dressing in general.
Edited by Harry B. Mason. One volume, pp.176. Published
by E G. Swift, Detroit. 1908.
Pharmaceutical teachers and scientists are evidently regarded as
a different sort of being from the regulation pharmacist. This is
what my friend Mr. Mason writes sending me a copy of his book :
"The Pharmaceutical Review is so scientific in character that I do
not suppose you will be interested in a book on 'Window Displays
for Druggists' which I have just gotten out. Nevertheless I am
sending you a copy. It may be worth a moment's consideration.
Do not trouble to make any reference to it in the Review unless you
really desire to do so." Yet A|r. Mason once upon a time wrote a
sketch of the writer in which he made his readers believe that the
subject of his biography was as transparent to him as though he
had applied a psychologic X ray.
The fact in the case is that when the writer got a glimpse of a
bibliographic notice of "Window Displays" he felt sore that he had
not been remembered with a review copy. Indeed the writer has
occasionally preached window displays to his students and has even
once forgotten his professional dignity to such an extent that he
wrote a short, article on the subject for a journal that makes no
pretense at being scientific but is professedly commercial in character.
So long as the exhib ts at our expositions are largely gotten up
along the lines of country fairs, we cannot expect our average
window displays to be arranged artistically or with an educational
motive. People who buy a newspaper because of the outrageous
headlines will, no doubt, buy toilet articles when their attention to
such articles is attracted by a display (2) that reminds one of the
charlatan who used to cry out his wares in public places. The dis
play of assayer's supplies (1), while not specially artistic, is neat
and in harmony with the more degnifled character of a drug store.
That so many displays belong to the category of which No. 2 is
an illustration, may merely mean that the taste of the American
public is not refined and that the average American druggist caters
to his customers. The fact, however, that there are also a goodly
number of the second class of which No. 1 is an illustration, must

be regarded as an encouraging sign. Might it not be a good idea
for the Editor of the "Bulletin" to secure the services of a true
artist for the purpose of working out designs that are botb original
and artistic? Pharmacy is so replete with subjects of greatest
interest to all that the undertaking ought to prove exceedingly
thankful.
The book is neatly gotten up and the character of the engravings
is good, much better, indeed, that that of many of the displays they
reproduce. It should be born in mind that the displays reproduced
are not suggestions made by the editor, but that the engravings
are those of displays that have actually appeared in the show
windows of American drug stores. To the uverage druggist the
book will be valuable in proportion to the number of suggestions
he may glean from its contents. To the writer its chief interest
centers in the fact that it crystallizes a phase of the American drug
store, that was, respectively is one of its chief characteristics at the
close of the nineteenth and the beginning of the twentieth century.
E. K.
Results of loco-weed investigation in the field by C. Dwight
Marsh; and Laboratory work on locco-weed investigations
by Albert C. Crawford. Bulletin No. 121, Part III, of the
Bureau of Plant Industry, U. S. Dept. of Agr., Washington.
Seventeen years1 ago the former editor of this journal criticized
the chemists of the Agricultural Department at Washington for not
having solved the problem of loco poisoning. Even at that time a
number of investigators had attempted its solution.2 That the
problem proved more vexing than it was supposed to be at first
sight even by some of our best experts3 experience has demonstrated.
And now after all of these years of search for alkoloids, toxic
albuminoids etc., we are told that this exasperating case of poison
ing is due to barium accumulated in the system, and that the loco-
weeds, grown on soil from which they do not take up this element,
are not poisonous. Phytochemists may learn the lesson from this
experience that the inorganic constituents of plants cannot be
ignored as they have been for some decades past.4 E. K.
t ) This journal. 7, p. 168.
a> Ibidem, p. 134.
») do £t, p. 8.
*) Comp. the "rlter'H renmrkH on the inorganic constituentH of the Btem ol
Denis uliglnosu Proc. A. Ph. A., 50, p. a31.
Volume 26. JUNE. 1908. Number 6.
Table for Preparation of Alcoholic Menstrua.
By A. B. Lyons.
To prepare from recovered alcohol, which of course varies greatly

in strength, a spirit of a certain definite percentage calls for a rather
troublesome mathematical calculation. The difficulty is that when
alcohol and water are mixed, condensation of volume takes place.
It is convenient, therefore, to make the necessary calculations once
for all, and construct from the results a table by reference to which
any individual problem may be at once solved.
The alcoholic menstrua most commonly prescribed are mixtures
of official alcohol and water in some simple ratio such as 1:3, 1'2,
1:1, 2:1, 3:1. These would be spoken of in ordinary parlance as
resp. "25%", "33^%", "50%", "66*%" and "75%", but they do
not in fact contain exactly these several proportions of official
alcohol. The actual percentages are approximately 25.4'/< , 34.0%,
51.4%, 68.37c and 76.5%. That is to say, to make 100 cc. of so
called "75%" menstruum you must mix 76.5 cc. of official alcohol
with water sufficient to bring the volume, after cooling, to 100 cc.
The volume of water required is 25.5 cc. It is assumed that the
measurements are all made at the standard temperature of 15.6° C.
(60° F.).
The accompanying table gives only the volume of official alcohol
required to make 100 volumes of a desired mixture (measured after
cooling). It is easy to calculate the volume of water, required by
referring to an alcohol specific gravity table. For example, a
(161)
"75%" menstruum is to be made from spirit showing by the

alcoholometer 82 per cent. By the table it is seen that to make
100 volumes of the menstruum we must take 88.6 volumes of the
82% spirit. The actual volume per centage of alcohol in the
menstruum must be 82 per cent, of 88.6, or 72.65. The specific
gravity of alcohol of this strength, according to the table in the
U. S. P., is 0.8771, so that the weight of 100 cc. of the mixture
will be 87.71 grams. The alcohol used (827c) had a specific gravity
of 0.8580, so that the weight of the quantity required to make
100 cc. must be 88.6X0.8580, or 76.02. Deducting th;s from the
weight of 100 cc. of the mixture we have 87.71 —76.02 = 11.69.
Since the specific gravity of water is 1.0000, this will mean that to
make 100 volumes of the desired menstruum, we must mix 88.6
volumes of 82% alcohol with 11.69 ± volumes of water. This result,
however, is only approximately correct, since in our calculations we
have disregarded atmospheric pressure. For exact figures, we must
have all weighings made in vacuo. For practical purposes of course
such refinements are unnecessary, and we need not even wait for
our mixtures to cool before adjusting the volume.
The table includes nearly all menstrua likely to be required. It
is not difficult to interpolate figures for any other ratios that may
be desired. Thus for "157" menstruum, take the mean of the
figures for "107" and those for "207 ". Suppose 1 have 16 gallons
of recovered alcohol showing 807 by alcoholometer, which I wish
to reduce to a "62J47." menstruum (i. e. a menstruum corresponding
with one made by mixing five volumes of official alcohol with three
of water). I find from the table that to make 100 volumes of
"607'* menstruum, I must use 73.2 volumes; to make the same
measure of "707 " menstruum, 85.0 volumes. The difference is 11.8.
One fourth of this is 2.95, and since 2% is one fourth of 10, this is
the figure we must add to 73.2 to give us the required volume,
which therefore will be 76.15. Then 76.15 : 100.00 : : 16 : x, and x =
21.01+ gallons. We must therefore add to the 16 gallons of recovered
alcohol water enough to bring the volume to 21.01+ gallons; the
fraction is negligible.
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PMARMACEVTICAL REVIEW. 167
Phytochemistry and Hayfever.
By F. RochuHsen.
Sea sickness and hayfever have this in common that while they
are not dangerous they annoy greatly the patients afflicted with
them. Both alike afflict body and mind without apparent
permanent detriment to the organism : they run their course and
disappear after shorter or longer duration. Indeed to those not
afflicted therewith, these diseases possess a tragicomic aspect and
are rarely taken seriously. For these reasons the etiology of the
two diseases has created but little interest, consequently their therapy
could not be very successful. Indeed until recently medical science
has been practically impotent in their treatment.
Particularly in the case of hayfever, which attacks only certain
individuals — for reasons that have not been understood until
recently — the notions of its cause have changed repeatedly.
Bostock, who first described it in 1819, regarded the first summer
heat as the cause. Klliotson in 18.'11 suspected that pollen of plants
produced the disease. This view was seconded by Blackley in 1873
who "made a detailed study of the subject involving no less than
seventy-six different plants. While these views were favored by some,
others denied any etiological connection between pollen and hay
fever. With the development of bacteriology the inevitable micro
organisms found their advocates, among them Helmholtz who him"
self was afflicted with hayfever. Again other investigators traced
the disease back to volatile oils or other emanations from flowers.
The question of the cause of hayfever was, therefore, by no
means solved. However, in recent years the correctness of the con
tention of Klliotson, namely that pollen is responsible, was proven
by Dunbar and his colaborers Luebbert, Prausnitz, Kammann and
others. As Director of the Hamburg Hygienic Institute, Dunbar with
his associates demonstrated in a series of experimental investigations
that the pollen of all (Iraminene as well as the pollen of certain
other plants such as lilly of the valley, asters etc., when brought in
contact with the mucous membrane of persons susceptible to .hay-

fever, produces typical irritations identical with those brought about
by natural hayfever.
The margins of the eyelids become swollen, a sensation of heat
is produced, also itching and redness; soon an inclination to avoid
light manifests itself more or less, the eye exudes a thick, sticky
fluid. After a short time the itching sensation extends to the nose,
somewhat later violent sneezing ensues, the nose flows profusely ajid
finally becomes clogged. With stronger intoxications more general
phenomena manifest themselves, such as oppression of the chest,
difficulty of breathing, heaviness of the head etc. The aggregate of
symptoms, therefore, is identical with that produced by genuine
hayfever. Furthermore, these intoxications could be reproduced with
the above mentioned pollens at any time irrespective of the period
of flowering, even in winter. However, they could be produced
exclusively in connection with hayfever patients, never with any of
the numerous normal persons presenting themselves for control.
Thus the hypothesis based on summer heat was excluded. In like
manner the sterile collection of pollen precluded the bacteriological
hypothesis of infection.
The etiology of the disease having thus been established, Dunbar
proceeded to isolate the active principle of the pollen. It could be
demonstrated that the poisonous action of the pollen was attribut
able to the pollen albumen, moreover, as was indicated by precipi
tation, to the albumin fraction. The pollen was triturated, the
albuminous substances extracted with 2Vi p. c. solution of sodium
chloride and the mixture centrifuged. The residue, when washed, no
longer produced any symptoms of irritation. From the centrifuged
solution the proteids were precipitated either with alcohol or by
dialysis with flowing water. In both cases the precipitate was
washed with alcohol and water. The residue resulting upon the
evaporation of the alcohol was also devoid of irritation-producing
properties. The hypothesis that the irritating action is due to
odoriferous principles soluble in alcohol thus had to be abandoned.
Other conceptions which brought hayfever into etiological relation
with nasal diseases or trigeminal neuralgia met with a like fate.
Whereas the therapy of hayfever had previously rested on a
purely empirical basis, new ways were opened to it since it had been
demonstrated that the active principle of the disease -producing
pollen is a toxalbumin. Behring had shown that it is possible to

neutralize the poisonous action produced by toxalbumins, or possibly
more correctly toxines, with the aid of immune serums. The earlier
experiments in this direction were conducted in connection with the
poisonous products produced by pathogenic bacteria. The serum
therapy of diphtheria, tetanus, various infections caused by strepto
cocci, and of several other infectious diseases is well established in
general medical and veterinary practice. Since then Behring has
also produced antitoxine serums against such phytotoxines as the
ricine found in the seeds of Ricinus communis, the abrin or "jequi-
ritol" isolated from the seeds of Abrns preratorius. The idea was,
therefore, not far fetched to prepare a serum containing an anti
toxine to the principle causing hayfever, which principle had been
shown to be affiliated if not identical with the toxalbumin fraction
of the pollenprotein.
In the first experiments made in this direction Dunbar operated
on rabbits and goats. After a relatively short treatment with pollen
"solutions" he obtained a serum which completely neutralized the
toxine. This neutralization was affected not only in the test tube,
but also in vivo when the serum was applied locally to the eye
revealing the symptoms of hayfever. It should be pointed out that
the serum was applied locally, not subcutaneously. Conclusive proof
of the correctness of the therapeutic hypothesis was furnished when
it was demonstrated that the serum would cure, rapidly or slowly
according to the degree of infection, hayfever produced by natural
causes.
Having demonstrated in a scientific way the possibility of a
curative treatment of hayfever, Dunbar proceeded to make his serum
therapy available to the medical profession. For the production of
serum on a large scale, small animals were not suited, but horses
had to be drawn into requisition. With what success the results of
the past five years have demonstrated.
With regard to the causal agents of hayfever, a distinction
should be made between two kinds, viz.: those that produce the so-
called European hayfever, the hayfever in the narrower sense of the
term, and those which produce the autumnal catarrh, so widely
spread in the United States. The former is les* known in this
country and is commonly referred to as spring cold, June cold ;
rose fever, peach fever. The autumnal catarrh is sometimes referred
to a fall fever. Whereas the symptoms of the disease are alike in

both oases, the causal agents are different. The spring cold is
caused by the pollen of grasses, notably those of rye, Indian corn
and wheat, the fall fever by the pollen of Ambrosia and Solidago
species. Whereas these seldom reach the blossoming stage in Europe,
they are common weeds in America.
The pollen can be collected in the following manner: Tin boxes,
90 cm. long, 20 cm. broad, and 3 cm. high, the narrower sides of
which are connected by a tin strip, are placed on blocks 10 cm. high
on a table in a light room. The table is covered with smooth
paper, the tin boxes placed at a distance of one meter apart, and
two-thirds filled with water.
When the flowers begin to open, the stalks are cut early in the
morning at a distance of M5 to 40 cm. from the tip, collected in
paper-lined baskets, and transferred as soon as possible to the tin
cases in such a manner that the stalks will rest at right angles to
the longer axis of the box. In order to avoid loss, the individual
stalks should be placed sufficiently far apart. In the water the
stalks continue to live and after several days the inflorescences begin
to shed pollen. The pollen is collected with the aid of cards and
dried in vacuum, for otherwise it would spoil in a relative short
time. Decomposition is indicated by sourness and t he appearance
of mould. Characteristic of fresh pollen is its malt-like odor re
sembling somewhat that of methyl salicylate. ■
A simpler method of collecting pollen consists in merely shaking
the inflorescences over paper-lined baskets out in the field without
cutting the stalks. This method, however, results in a much smaller
yield. The yield of pollen is largest about the middle of the flower
ing period and depends largely on the weather before and during
this period. During cold or rainy weather a satisfactory yield can
not be counted upon.
In Miltitz the flowering period of winter rye was from May 29
to June ;} in 1905. from May 29 to June 6 in 1900, and from May
29 to June 4 in 1907. The flowering period, therefore, was practi
cally identical during these time years, although the season of
1905 was warm and clear, that of 1900 cold and rainy, and
that of 1907 cool, dry and fairly clear. Sum tner rye flowered shortly
after the winter variety, thus, from June 11 to 16 in 1900. In the
previous season, 1905, it also followed closely upon the flowering
period of winter rye, but, owing to the warm weather, the period
lasted but a single day. The flowering period of the Indian corn
lasted from .July 12 to 17 in 1905, and from August 30 to Septem
ber 25 in 1906; that of Ambrosia nrtemisiaofoliu from August 24
to September 17 in 1905, and from September 11 to October 22 in
1906. Solidago virgn avrea flowered from August 15 to September
28 in 1906, and from September 15 to October 20 in 19«7; whereas
the corresponding periods for Solidago shorti was August 16 to
September 28 in 1906, and from August 15 to September 18 in
1907. It becomes apparent, therefore, that the climatic differences
made themselves felt in those plants that were foreign to the field
of observation.
The yield per tin box varied considerably. In the case of Indian
corn it varied from 14 to 22.5 grams, in the case of winter rye
from 6.5 to 12 grams, and in the cose of summer rye is amounted
to 4 grams. The vacuum dried pollen is transferred to brown-
colored bottles stoppered with cotton mid kept in a dark, cool
place. Under these conditions the pollen can be kept for a long
time without appreciable loss of toxicity.
If a horse is to be injected with a pollen "solution"' several
grams of the pollen are transferred to a disinfected porcelain mortar
and triturated with sharp sand that has previously been heated to
a high temperature. Gradually eight times the amount of a sterilized
2% per cent, sodium chloride solution, containing % per cent, of
phenol, are added. The gradual disintigration of the pollen grains
is controlled microscopally. The mortar is then covered and kept
for Hix hours in a drying oven at 45°.
Larger amounts of pollen are triturated for several days in a
closed porcelain ball mill with the aid of flint pebbles and sand,
the comminuting apparatus and material having previously been
sterilized. The aqueous liquid resulting is centrifnged from the sand,
the pollen coatings etc. which are also washed. The pollen "solu
tion" thus obtained is used for injections.
In order to test a horse with regard to its susceptibility to the
toxine contained in the pollen, it receives the injection from % gram
of rye pollen. If susceptible, local swellings become appearent, the
temperature rises about 1° to 2° and the animal refuses feed. The
inoculations are then repeated from time to time with increasing
doses until a sufficient amount of antitoxine has been formed in the

blood serum.
The development of antisubstances is determined in accordance
with the same principle adopted in the manufacture of other serums.
However, this difference is to be noted, viz. that whereas in the
production of other serums animals can be used as test objects, in
the production of hayfever serum man has to be employed for the
reason that the hayfever poison apparently attacks, man only.
Experiments have been made repeatedly to produce in animals the
symptoms of hayfever by injection of pollen solution, however,
always with negative results.
As a test object the human eyes are necessary into which mix
tures of toxine solution of known physiological strength and of
serum are dropped. Luebbert describes this testing of the antitoxine
in the following manner: "First of all the concentration of a rye
pollen proteid solution is ascertained of which one drop, when intro
duced into the conjunctival sac, will still produce within several
minutes a subjective as well as an objective reaction. This termed the
Dosis toxica minima. Then a series of mixtures of toxine and anti
toxine is prepared. That mixture which no longer irritates the eye
of the patient is designated as the neutral mixture. The valence of
a serum is determined, therefore, by the degree of that dilution which
still possesses the capacity to neutralize the simple toxine dose.
This determination is accompanied with an error not exceeding ten
per cent.
This method presupposes that the physiological activity of the
test toxine is not changed. This is the case, for, while solutions can
be kept only a few days, the dry toxine is stable, as has been
demonstrated by an experiment comparing it with a standardized
dry serum, during a longer period of time.
Whereas there are certain disadvantages associated with the
titration of the serum in the human eye, there are also certain
advantages that are not to be underestimated. Even the slightest
excess of toxine not neutralized by antisubstances, though it may
no longer be indicated objectively by means of a redening of the
conjunctiva, is indicated subjectively by means of the sensations of
itching and burning of the eye. These subjective indications while
they can not be observed in the experiments on animals admit of
a more accurate titration of the serums.
For practical purposes a strength of 40 of the horse serum is

attained although it can be brought as high as 50 and even 60.
This implies, as already indicated above, that when diluted forty-
fold, the horse serum will neutralize an equal volume of a toxine
solution diluted to such an extent that it will still produce an irri
tation. Until the serum of the horses reveals a sufficient antitoxine
content the inocculations must be continued with ever increasing
doses of pollen extract for from one-half to three-fourths of a year.
During the intervals, i. e. about 10 to 14 days after the inoccula-
tion, about 1 to 2 ccm. of blood are drawn from one of the principal
veins for the purpose of making a test. According to the results of
this test the inocculations are continued or blood is withdrawn for
the preparation of the commercial serum.
The withdrawal of blood for the latter purpose is conducted by
a veterinary surgeon with the aid of a tubular needle inserted into
the jugular vein. Through a rubber tube the blood is passed into
a so-called Calmette jar in which the blood cake is expressed by
means of metal plates coated with tin thereby securing a larger
yield of serum than can be obtained by collecting the blood in
cylinders. It need scarcely be mentioned that all of the implements
used in the pollen injection as well as in the withdrawal of blood
are sterilized, indeed that the entire procedure is conducted in
accordances with the rules of asepsis. In order to attain a good
yield of serum Lt is of importance to regulate carefully the tempera
ture of the room in which the blood-jars are kept. It is likewise
important that the horses should be quiet before as well as during
the withdrawal of blood. As a rule the withdrawal can be accomp
lished without the loss of a drop of blood. The average yield of
blood is 10 liters: smaller horses up to 400 kg. weight yielding
8 1., larger horses up to 500 kg. weight yielding 12 1. of blood.
Like withdrawals occur generally every 4 to 5 weeks. That the
horses receive the best of care, are exercised regularly, in winter as
well as in summer, and that they do but little work need scarcely
be mentioned.
In the preparation of liquid pollantin the following process is
followed : The serum from the Calmette jars is transferred to
sterilized Erlenmeyer flasks, five percent of an aqueous 5 per cent
phenol solution are added, and the liquid set aside in a cool place
for several months. The phenol is added as a preservative, a practice
174 PHARMACEUTICAL REVIEW,
that is likewise followed in the preparation of diphtheria serum. It

also causes albuminous substances to be thrown out of solution as
a llocculent precipitate which is removed by filtration. The clear
filtrate, bottled by means of a suitable apparatus, constitutes the
PollaDtinum liqnidum of commerce.
A temporary turbidity is nevertheless caused occasionally by the
continued precipitation of albuminous substances or by small scales
of paraffin used in paraffining the sterilized corks. Turbidity due to
these agents will disappear if the container be set aside over night
or after 24 hours, causing the particles to subside, and leaving the
supernatent serum perfectly clear. These disturbing agents are
perfectly harmless as has been shown repeatedly.
A permanent turbidity caused by harmful bacteria due to care
less handling of the liquid preparation, however, is a different mat
ter. The sensitive liquid pollantin should, therefore, be kept with
the greatest care for the success of the treatment with this remedy
depends largely on its good condition.
For these and other reasons, pollantin in powder form has met
with more general favor than the liquid preparation. It can be
handled more readily, it admits of more exact dosage, and, as recent
experiments made in the Hamburg Hygienic Institute have demon
strated, it can be kept for years without change. Another factor of
importance to patients sensitive to phenol is this, that the pulver
ulent pollantin is free from phenol or other preservatives.
In the preparation of solid pollantin the serum from the Calmette
jars is decanted into sterilized, shallow dishes which are transferred
to vacuum drying ovens and heated to at most 45° for several
hours. As a residue there remain 8 to 10 per cent, of a light,
yellowish-brown, glue-like and hygroscopic mass. This is transferred
to a sterilized porcelain ball mill and reduced to an impalpable
powder. It is then sieved and the sittings mixed with a definite
amount of sterilized milk sugar. Such admixture is necessary not
only because of the hygroscopic character of the dried serum, but
also because when thus reduced the serum can be applied much
more satisfactorily to the mucous membranes. The hygroscopic
powder itself would cake upon application and thereby be rendered
more or less ineffective. In the dried, reduced form, pollantin is no
longer attacked by bacteria. The filling of this pollantin powder
into suitable containers is effected by means of a machine which can
readily be sterilized and which will measure off 1000 exact doses
within an hour.
Before being transferred to the small containers for market,
each batch of pollantin, powdered as well as liquid, is examined by
the Hamburg Hygienic Institute to ascertain the absence of germs.
The liquid preparation is only then allowed to be placed upon the
market if perfectly free from germs. A number of samples, which,
because turbid, were supposed to contain bacteria, were without
exception free from bacteria, the turbidity being due to precipitated
albumen as explained above.
The results from the use of pollantin in the United States were
even more satisfactory during the past year than during previous
years, as will become apparent from the following data.
1907. Iit06. 1905. 1904.
Fully effective. ...54 p. c. 51 p. c. 52 p. c. 45 p. c.
Partially effective 38 " 38 " 30 " 26 "
Negative 8 " 11 " 18 " 29 "
The diminution in the percentage of negative cases is, no dou bt
due to a number of causes. Some patients applied too large doses
of pollantin and thus irritated the mucous membranes mechanically.
When advised to use smaller doses they attained better results.
From answers to queries obtained from European patients it was
ascertained that many had expected to make a more formidable
attack upon the disease by using larger doses of pollantin. Instead
of obtaining relief they made matters worse. It is much better to
apply the remedy in very small amounts, as small as a pin's head,
and to apply it oftener.
Another class of patients not benefited are those who are sus
ceptible against all foreign serum, i. e. obtained from animals.
Pollantin, therefore, irritates them in like manner as does the pollen.
In all instances in which these cases could be examined, this form
of idiosyncrasy could be proven by the application of normal horse
serum, i. e. free from antitoxine, to the mucous membranes. The
results were identical with those produced by pollantin. The idio
syncrasy having been established, this class of patients could be
helped by supplying them with a pollantin diluted to a larger extent
with milk sugar.*
• Such a preparation has been designated "Pollantin R."
A third class of patients receiving negative benefit is due to false

diagnosis, a nervous catarrh being taken for hayfever. The premisis
being wrong, pollantin therapy cannot be expected to bring relief.
In order to ascertain whether a patient is affected by nervous catarrh
or genuine hayfever, produced by the resorption of pollen poison,
physicians are supplied with a diagnostic agent. This consists
essentially of a dry mixture of pollen proteid and sodium chloride.
For the ready application of this diagnostic agent a tube is also
supplied in which it can be dissolved with the aid of distilled water.
This concentrated mother solution is applied, at first greatly diluted,
to the eye to be examined. By gradually applying stronger solutions
the degree of hayfever susceptibility can be ascertained. Only such
persons as are susceptible to hayfever will be affected by this agent,
others not. In the diagnosis of European hayfever this method has
proven very efficient.
Pharmaceutical Pot.
Keber Collection.
PHARMACEUTICAL 1CEVIEW. 177
Phytochemical Notes.
From the Laboratory of Eilward Kremers.
68. California Eucalyptus Oils.

Perhaps the best account on the growth of eucalyptus trees in
California is to be found in an official bulletin of the Department of
Agriculture. Inasmuch as the forester's point of view naturally pre
dominates, little of phytochemical interest is contained therein, yet
the following extract will prove of general interest and may, there
fore, serve as introduction to this preliminary report.
"The eucalypts are now grown in America, especially in the
southwestern United States, more extensively than any other exotic
forest tree. During the past forty years they have been planted
here and in other parts of the world for ornament, for sanitary im
provement, for shade, for wind-breaks, for fuel, for oil, and for tim
ber; and incidentally they have been useful in many other ways. In
fact, they have probably served more aesthetic and utilitarian pur
poses than any other forest trees that have been planted on this
continent." 1
Somewhat more information concerning the distillation of the oil
can be gleaned from the semi-annual reports of Sehimmel & Co.
The first reference to American eucalyptus oil made by them
appears in 1887.-' They call attention to the overproduction of the
preferred globulus oil in Australia and that the commercial depression
is aggravated by the new competition that has arisen from California.
In the same year3 they refute certain claims of inferiority made
by English chemists which involve California oil. The public is also
informed that since 1884 oil of Eucalyptus globulus has been distilled
on a commercial scale as a by-product in the manufacture of an
anti-incrustator for boilers. Although this source had not been
t Bulletin No. .'i5 of the Bureau of Forestry, l\ H. Pepurtment of Agriculture:
A. J. McClaU-hie, — Euculypts cultivated in the I'nlted Statis.
2 Btricht S. & Co., April. 'S7, p. 14.
» Ibid., Oct., 1SS7. p. 12.
generally known, their New York branch had obtained as much as

several thousand kilos of an excellent oil, rich in cineol, from this
industry.
The name of the distillers is revealed the following year,4 viz.,
the Downie Boiler Incrustation Preventive Co., operating in Alameda
County near San Francisco Bay.
In the fall of 1888 the California output, several thousand
pounds of which are reported as being in the market, prevented the
contemplated increase in the price of the Algerian oil.5
1) General View of Mr. Schueddig's Plant.

Still houHe with gum trees in the rear.
In 1889° the California oil could be placed only with difficulty
owing to the overproduction of globulus oil in Algiers. Moreover,
it had been dropped by this firm because of the variation in its
cineol content.7 The distillers in California were then placing euca-
lyptol as such on the market, a. fact that is made to account for
the occasional inferiority of the commercial oil. A normal oil should,
according to their standard, contain from 50 to 70'/ of cineol.
* Ibid., April, 1888. p. 18. « lbid., April. 1889, p. 18.
o Ibid., Oct., 1888, p. 14. 1 Ibid.. Oct., 1889, p. 26.
In 18(.)2, eucalyptus oil became a popular favorite during an

epidemic of influenza in England. The result was a high price until
Californian as well as Australian oil appeared in the British market.8
In 1893 the California oil is reported as stepping more and more
into the background,9 but no reason is mentioned.
The general arrange-

ment of the Htill resembles
that oT the one Illustrated
in A*. 43, p. 74 of G.-H.-K.,
The volatile oils. However,
the body of the still in
which the leaves are packed
Is of wood, the stillhead Is
of copper lined with tin,
likewise all pipes incl. con
denser.
Private communication
by P, E. .Schueddlg, May
23. 1904.
2) Interior of still house of P. E. Schneddlg.

For more than a decade no further reference is made to the
California distillate. In 1906 the following statement is made10:
» Berlcht 8. & Co., April. 1892, p. 17.
io» Ibid.,
Ibid., April,
April, 1898, p. 22.
29.
1906. p.
"According to Jackson,11 the Smithson Development Company oi

Rafael, Cal., uses eight tones of leaves daily which are distilled with
steam under pressure."
For several years past the writer has had occasion to come into
touch with several of the distillers in California. Though but scant
returns were the result of several inquiries made thus far, it may be
of interest to record even the little information acquired. First of
all, it should prove of some slight value to record the names and
addresses of those who have engaged in the distillation of eucalyptus
3) Laboratory with still for refining.

oil in the United States together with such data as have been
acquired. Possibly the publication of this brief descriptive catalogue
of producers may lead not only to n. completion of the list, but also
to further detailed information.
In a private communication under date of Oct. 30, 1900, Dr. F.
D. Dodge kindly informed the writer that the firm of Dodge <£
ii Am. Dr. & Ph. lice, 1 ii<<->, p. .117.
Olcott Co. had done a "small" business in American eucalyptus oils.
Their records show analyses of a few lots between 1895 and 1900.
Oil Eucalyptus Globulus
TRIPLE DISTILLED
WARRANTED ABSOLUTELY PURE
MADE BV F. E. SCHUEDDIG
THE PALMS. LOS ANGELES COUNTY. CAL.
EXTRACT OF V. S. GOVERNMENT REPORT

Bulletin No. 35
Eucalyptus oil is so useful, and popular, information concerning it is so
meager, that a few words concerning it will not be out of place here. This
oil has been used for about forty years, but only during the past ten years has
it been employed in medicine very extensively. Its use is now constantly
increasing, as its properties and medicinal value become better known.
The fact that it is non-poisonous and non-irritant makes it especially safe
and valuable. As much as a fourth of an ounce has been taken internally
without injury, and it may be freely applied to the most delicate tissue.
Notwithstanding the fact that it is neither dangerously poisonous nor irri
tating to the human system, it is a very effective antiseptic and disinfectant,
and has come to be used quite extensively for dressing wounds, ulcers, and
other diseased tissues. It enters into the composition of several antiseptic
preparations. The oil is also a well known remedy for malarial and other
fevers, and is used in treating diseases of the hair and skin, and of the stom
ach, kidneys, and bladder, and is especially valuable for affections of the
throat, bronchi and lungs.
jgtfln using Eucalyptus oil it is important that a pure article be procured.
Unfortunately there is a cousiderable adulteration of this oil with cheaper,
inert, or harmful ones. No doubt this remedy would be a more popular one
but for the fact that so much of the oil for sale on the market is of such
an uncertain nature. The safest way is to purchase none in bulk, but buy it
in bottles put up by a reliable person or firm It costs more in this form, but
is far safer to use as a remedy.
4) Facsimile reproduction of advertisement.
These were low gravity oils (0.913—0.915) and inferior in eucalyptol
content to the Australian variety.
F. E. SCHUEDDIG, The Palms, Los Angeles. '»

Mr. Schueddig began the distillation of eucalyptus oil in 1893 in
an experimental way. Since 1899 he distils the oil on a commercial
scale, having distilled about 1000 pounds of oil the first year, and
about 5000 pounds of oil the year before last.
As material for distillation he uses globulus leaves exclusively.
He distils throughout the year provided he can get leaves, the
resulting oil being about the same in quality and yield irrespective
of the season. From fresh leaves the yield is about 1.27%. From
the partly dried leaves a somewhat smaller yield is obtained, but
the yield of oil is naturally slightly reduced when the crude oil is
rectified.
Mr. Schueddig disposes of his oil to ninety-six retail druggists
and to the two wholesale firms at Los Angeles. The price paid for
his oil is about the same as that paid for imported oil, ranging
from $1.50 to $1.75 per dozen one ounce bottles, and from $1.15
to $1.25 in one pound bottles.
The oil is prescribed by physicians and is used by the local
population as a household remedy. It is also used in the manufac
ture of popular remedies, e. g. Euca-mul and Euealoids.13
The accompanying illustrations will give a fair idea of the out
fit emplojred by Mr. Schueddig, who has kindly supplied the writer
with information and photographs, also with material for experi
mental work.
DOWNIE BOILER INCRUSTATION PREVENTIVE COMP,
Alameda Co., near San Francisco Bay.
According to Schinnnel & Co., 14 this company began the distilla
tion of eucalyptus oil as a by-product in 1884, and evidently placed
upon the market several thousand pounds of oil in a single year.
The manufacture of cineol and the simultaneous deterioration of the
oil marketed, seems to have been followed by dire results.15
N. C. HERON, Los Angeles."5
Dr. Heron, who began distillation in an experimental way in 1891,
and on a commercial scale in 1895, states that he has distilled from
i» The data here recorded are taken from a private communication bv Mr.
Schueddig dated Sept. 2, 1906.
'» Manufactured bv Edw. G. Binz, Loa Angeles, Cal.
i* Bericht 8. * Co., Oct.. 18S7, p. 12: alao April, 18*6, P. IS: etc.
>» Ibid., Oct., 1S89. p. 26.
i« The data here given are baaed on answera to a list of queries submitted in
August l'JOti.
If You Waul Pure Eucalyptus Oil Btt Heron's

FULL DIRECTIONS ON EACH BOTTLE
' PURITY , ■ E?
HEALTH VAQt J5JKJ M"* STRENGTH ,
£ DR. HERON'S EUCALYPTUS REMEDlES 5

O AND THEIR USES =*
r~ Heron's Eucalyptus Oil is the best and cheapest remedy for all Cough*. Colds, GO
tr% Whooping
v* Cough. Bronchitis,
stages. Asthma. Croup. Diphtheria. Tonsihtis,
Sore Throat. Fevers Catarrh, Consumption
of all kinds. Headache*inEarache,
its first a
ca
Toothache. Neuralgia, Rneumatism, Dyspepsia, Kidney Disease, Gravel, Sprains, ""**
Bruises. Burns. Insect Bites. Poison Oak, etc. Price, 50c.
\J Heron's Eucalyptus Salve is the safest and quickest remedy for all Skin
_ Eru1 cions. Sore Lips, Cold Sores. Chapped Hands, but especially for Eczema, Salt
J Rheum and Piles. Price. 25c. 3r
fy Heron's Eucalyptus Hair Restorer is a fine preparation for the Hair. Re-
LL moves Dandruff, cleanses the scalp, prevents the hair from falling out, cures all
□ Scalp Diseases, and restores the hair to its natural color, and never requires wash
ing as this keeps it clean and perfect, and by its continued use a luxuriant growth of
the hair is obtained. It is not a dye. Price, 50c.
Heron's Cream of Eucalyptus. A Skin Beautifier and Food. Removes, not
I covers. Tan, Pimples, Freckles, Moth Patches, Rash, and all skin disorders, leaving
the skin soft and beautiful. Price, 50c.
J Heron's Eucalyptus Specific THE LADIES' FRIEND, or Nature's Own
< Remedy for all Female Diseases. Cures Leuoorrhoea, Ulceration, Falhng of the
Womb and all Female Disorders. For heahng and cleansing purposes it has no equal.
Price, $1.00.
Heron's Eucalyptus Cough Drops are a very fine preparation of extra fine
L*. oil and pure sugar. For reheving all irritations of the throat; Dry and Hacking
- Coughs, etc They will be found especially beneficial for children. Price, Be.
^ Heron's Blue Gum Liniment. Wherever a Liniment can be used this will
be found the cheapest and best. Price., 50c,
Heron's Constipation Cure and Liver Regulator is the only permanent
|j | cure known for the Liver. Stomach and Bowels. It has no equal. Price, 50c. and $1.
J Heron's Nerve Tonic Cures all forms of Nervousness, builds up the waste
tissues of ths system, and will be found the best reriedy that has ever been tried
<for a rundown constitution. Price, $1.00.
Heron's Eucalyptus Soap. A Tine Toilet Soap, antiseptic and disinfectant
Cures all eruptions of the skm, and is advised by the best physicians to be used
as an every-day Toilet Soap. Price, 30c. a box.
Heron's Diamond Tooth Powder. An elegant and economical Dentifrice.
Hardens the gums, and removes all tartar from the teeth, leaving the enamel in a
perfectly pearly whiteness. Price, 25c.
Q Take no other. None genuine without the name and address of the only manu-
7* facturer of Pure Eucalyptus Remedies.
DR. N. C. HERON CO. U
338 W. JEEEERBON 8T„ cor. Hope LOS ANGELES, CAL. CO
We Do Not Sell Our Oil in Bulk

BE SURE OF THE NAME AND ADDRESS
ORDERS BY MAIL WIL . RECEIVE PROMPT ATTENTION
BEWARE OF IMITATIONS
Si Facsimile reproduction of Dr. Heron's advertisement.
two to eight thousand pounds of oil each year from Eucalyptus

globulus. His period of distillation is restricted to the months of
January und February. The yield from fresh leaves is about 1%;
that from dried leaves %%.
The oil appears to be used exclusively for "Dr. Heron's eucalyptus
remedies," no oil being sold in bulk. Local enthusiasm, together
with real and imaginary sick pilgrims to the "Golden State" as well
as real therapeutic value of the oil seem to have provided a market
for quite a variety of eucalyptus remedies as becomes apparent from
Dr. Heron's circular herewith reproduced.
"He does not distill out any eucalyptol, as he considers the oil in
the form he puts it out superior for most purposes. The residue
from the distillation of the refined oil from the crude product is put
up for a solve. From the oil he manufactures a soap and cough
drops." 17
E. L. WITTE, Los Angeles.
Mr. Witte has for some time been interested in the oil-producing
eucalypts. He has kindly sent the writer a small sample of oil from
Eucalyptus sulubris and is engaged in the cultivation of a number
of species of Eucalyptus for the production of oil in an experimental
way.
SMITHSON DEVELOPMENT CO., San Rafael.
No reply to the circular letter sent out was received from this
company. This is probably the concern of which Prof. Albert
Schneider states17: "Eucalyptus oil is manufactured by a San Rafael
firm on a fairly large scale. They obtain it from E. amygdalina."
H. B. SELKIRK, Los Angeles.
No reply to the circular letter sent out was received.
ELLWOOD COOPER, Santa Barbara.
"Hon. Eilwood Cooper has a young Blue Gum plantation on his
ranch near Santa Barbara, from which he intends to manufacture
both eucalyptus oil and eucalyptol." 17
H. B. SILKWOOD, Garden Grove.
"H. B. Silkwood, proprietor of the California Eucalyptus Works,
Garden Grove, Cal., reports that he produced 1 ton of oil from 100
tons of material during the past year (1901), the output being
limited to the available supply of Blue Gum lea»es.'"17
Last, but not least, should be mentioned the experimental work
of Dr. S. 1i. Woodbridge, 18 incorporated (pp. 283—287) in the
monograph of Abbot Kinney.19 The investigation covered not less
than twenty-three species. However, it is not the intention of the
writer to report on the physical and chemical characteristics of the
Californian eucalyptus oils at the present time. Samples received
from distillers, particularly from Mr. Schueddig, have been partly
examined. As soon as this work has progressed to a more satis
factory stage, a report will be rendered.
* " McClatohie, I. c. p. .'19.
if Privjite communication under date of May 11, 190S.
ts Lob AnIeeles. Cal.
i» "Encalypts." Publ. by B. K. Bauiugarth Sc. Co., I.o* Angeles, Cal.
Plant Pigments.*
By /. W. Brnndel
From about 1855 on, the attempt at explaining plant pigment

ation on the basis of the relation of pigments to chlorophyll, was
gradually abandoned. However, the idea of basal substances under
lying the different plant pigments, or groups of pigments, in all
flowers without being related to chlorophyll, was still held for some
time. But gradually the discovery of new plant constituents and
their derivatives led to attempts to explain the color of limited
groups of flowers.
Previous to this time, Huenefeld24 in 183!) had already made an
attempt to get away from the idea of plant pigments being modified
chlorophyll. From the behavior of a large number of flowers to
wards different solvents, the conclusion was drawn that plant pig
ments have certain radicals, as a basis, which, however, are different
in different plants. 'Die Pflanzenfarben gehoren mit zu den am mei-
sten speciell metamorphosirten Stoffen.' They are specific substances
like the volatile oils, even if their manifoldness can be brought about
by very simple means. The color changes produced by the fading
or dying of the flower are due to the fact that with the retarded
vegetation, the consumption of carbon ceases and the absorption of
atmospheric oxygen increases, thereby destroying the pigments.
Among all the plant physiologists who had studied plant
pigments up to this time, Preisser-'5 was the only one to re
gard plant pigmentation from a standpoint entirely different from
that of his co-workers. He attributed the color in any one plant to
the presence of a chemically definite plant constituent, which was
peculiar to that plant or allied plants. To his mind, therefore, the
study of plant pigments meant 1) the study of such colored plant
constituents, like quercetin, luteoline, indigo, morrin, etc., as were
• Continued trom page 150.
a* Joarn. t. prukt. ( hem., 16. p. 65.
»5 Journ. de Pharm. et de f'him. (3) 88, pp. 191, 241i.
known at that time; 2) a study of the chemical changes which

commonly go on in a plant; and 3) a study of the changes brought
about in the various colored plant constituents when subjected to
similar chemical reactions. He makes no mention whatever of mix
tures like cyanine, xanthine, etc., commonly studied by plant
chemists. He speaks of chlorophyll only to say that it must be
more thoroughly studied. In the roots of all plants there is a
constant process of reduction going on forming derivatives of the
plant pigments, which are not colored. In the leaves and flowers,
however, a process of oxidation is going on so that all the modifi
cations of color noticed in the same plant are derived from the same
plant constituent in different states of oxidation. Thus the brown
color of Rhus cotimis is due to the yellow fustin, which has been
changed by the action of ammonia and the oxygen of the air. It is
for this reason that the color of a plant can be destroyed with
reducing agents and restored ngi1in with oxidizing agents. Preisser
also thought that these colored plant constituents did not exist in
the plant as such but as their metallic derivatives, especially sodium,
potassium and ammonium.
Fremy and Cloezaa in 1854 were the first to object to regarding
pigments as derived from chlorophyll on the ground that neither the
pigments nor the chlorophyll had been obtained in a pure condition
and, therefore, no such conclusions were warranted. The main object
should be to determine what the pigments themselves are. According
to these authors there are three pigments found in plants. Cyanine
is the pigment in blue flowers. This is a blue amorphous substance
which dissolves in alcohol to a colorless solution and upon evapora
tion leaves a blue residue. The red or rose colored flowers owe
their color likewise to cyanine which is changed in color by different
degrees of acidity of the plant juice. The yellow pigments of flowers
have no relation to and can not be derived from the red or blue pig
ments as claimed by others. There are two entirely different yellow
pigments found in flowers. These two pigments are not related to
each other and are called xanthine and xantheine. The fact that
some yellow flowers turn red is explained by assuming that the
flowers also contain some cyanine and as the yellow pigment is
destroyed the cyanine shows up its color.
ae Journ de Pharm. (3) 2.">, p. 249.
{To he continued. I
PHARMACEUTICAL, REVIEW. 187
Literary.
Books Reviewed.
Outlines of industrial chemistry. A text-book for students by
Dr. Frank H. Thorp, Asst. Professor of Industrial Chemistry
in the Massachusetts Institute of Technology. Second edition,
revised and enlarged and including a chapter on metallurgy
by Charles D. Demond. One vol., pp. XXV, 618.
Thorp's "Outlines" constitutes not only an attractive volume,
but a rather formidable one if one rememlwrs that it is intended
"to furnish an elementary course in Industrial Chemistry, which may
serve as a ground work for a more extended course of lectures, if
desired.'' That as such it admirably serves its purpose the writer
has had occasion to experience. Yet even as a "ground work" it is
to be regretted that the subject matter is so exclusively technologica'
and that the historical and economical aspects of the subject receive
but little attention. Both the chemical engineering student and the
student of chemistry who prepares for industrial work are only too
apt to narrow their undergraduate studies to as nearly a purely
technical course as possible. Above many of his chemical colleagues,
the teacher of industrial chemistry enjoys the possibility of intro
ducing humanizing elements into his materia cbemica. This oport-
unity should not be left well nigh exclusively to the lecture but
Bhould be reflected in a text-book as well. The author has made
occasional attempts in this direction, but evidently with a certain
sense of fear and trembling lest a good thing be overdone.
Industrial chemistry, though a special branch in a large depart
ment of science, is itself so broad that it is practically impossible
for one person to keep in touch with recent developments along all
lines. The array of colaborers enumerated in the preface would seem
to insure sufficiently against any shortcomings in this direction.
However, the specialist will have no difficulty in finding a number of
errors in his particular Held.
Thus e. g. the chapter on essential oils is extremely inadequate.
While it is true that several citrus oils are obtained by so-called
"pressing'", "hydraulic or screw presses" are not employed. These

are used, it is true, in the expression ot the juice in the manufacture
of citric acid from the pulp, but not in the preparation of the oil,
where handpressure — involving skill much more than force — alone
is employed. Of the most important American oil, viz. oil of tur
pentine we read that it consists of a terpene, C1oHia, called austra-
lene. Why the term dextropinene was not employed, thus bringing
out the relationship to French turpentine oil, is incomprehensible.
Of the American oil next in importance we are informed that "it is
a mixture of menthol, C10H19OH, with several terpenes." Of menthyl
esters and of the commercial valuation of peppermint oil according
to its menthol and menthyl ester content not a word is said. In
deed it would seem that the subject of assay of volatile oils was not
regarded of sufficient importance to be mentioned even in a general
way although it is only too sad a fact that volatile oils lend them
selves so readily to sophistication. Oil of wintergreen, a third
American oil, we are told "is distilled from the leaves of Gaultheria
procambenfi.'' That it" should so be distilled to be true to label
there can' be no doubt, but the student of industrial chemistry at
least should likewise be informed that most of the so-called natural
wintergreen oil is distilled from the inner bark of sweet birch. These
and similar instances lead one to suspect that while the author
refers his readers to a number of special treatises on the subject,
he himself, or possibly his colaborer, have not taken the trouble to
consult these works themselves when this particular chapter was
revised.
However, faultfinding in the line of ones own specialty is rather
easy. A reviewer should, therefore, not indulge overmuch in such
criticism. As a matter of fact, in his review of the first edition,*
the. writer refrained from attention to these and similar details.
There are, however, rather serious misstatements in other
chapters. One which the writer happened to notice (p. 424") is this
that "For distilling potato mashes, vhich are thick and slimy, no
continuous acting still has proved successful, and the intermittent
Pistorius apparatus .... is much used." While it is true that the
Pistorius apparatus is still used in some of the small plants installed
e. g. in Bavaria fifty years ago, the writer found continuous acting
stills on all the estates which he visited in Germany during the post
• This journal, vol. 24, p. OH.
winter. While ten years ago such a misstatement as the one quoted
above might have been of no consequence whatever; it is a matter
of some importance to-day, when efforts are being made to introduce
the potato alcohol industry into this country, that the rising
generation of industrial chemists be not grossly misinformed in this
particular.
If the writer has pointed out a few shortcomings, as they appear
to him, he does not want to be regarded as doing this in any spirit
of faultfinding. If criticism be taken at all seriously, each reviewer
i. e. to the extent of his review — should become a true colaborer
with the author. It is because of the interest which the writer takes
not only the subject of industrial chemistry but more particularly
in this book, that he has gone into some detail. As a text-book,
Thorp's "Outlines'" is far above the average. Those who are at
all familiar with the character of the books of this firm of publishers
possibly need not be told even this much. E. K.
Ki rzks Lehrhuch der organischex Chemie von William A. Noyes,

Professor der Chemie an der Fniversitiit Illinois. Mit Genehmi-
gung des Verfnssers in's Deutsche iibertragen von Walter Ost-
wald und mit einer Vorrede von Professor Wilhelm Ostwald.
Ein Bd., pp. XXIV, 722. Akademische Verlagsanstalt m. b. II.
in Leipzig. 11)07.
Germany is not only the home of bookmaking par excellence,
but for several generations at least she 1ms turned out more chemi
cal literature than possibly any two other countries combined. •
Moreover, since Liebig introduced the laboratory method of study
and followed up this revolutionary pedagogic act with a text-book
on organic chemistry that has served as a model to other writers
for possibly several generations, Germany has unquestionably taken
the lead not oidy in the instruction of chemistry, but also in the
writing of chemical textbooks. No one is surprised, therefore, to see
a German book translated e. g. into English even though the book
in question possesses no special merits, for such has been the tradi
tion. If, however, an English textbook is translated into German,
we naturally look for the reason why.
If a man like Ostwald writes the preface to the German trans
lation of such a book, one feels justified in looking to this introduc
tion for an explanation. In this we are not, disappointed and we,
herewith, quote the German master's own words: "Bei der ganz un-
iibersehbar gewordenen Masse einzelner Tatsachen, die alle dem einen
Gebiete der organischen Chemie zugerechnet werden miissen, ist es
jedem Anfanger von entscheidender Bedeutung, die Grundziige des
systematischen Zusammenhanges dieser Tatsachen so bald und ein-
dringlich wie moglich bewiiltigen zu konnen. Durch die eigenartige
Anordnung des Stoffes ist es nun in der Tat moglich geworden,
eine solche Symmetrie und I'ebersichtlichkeit des gesamten Materials
herbeizufiihren, dass der Student, welcher dieses kleine Buch kennen
gelernt hat, seine weiteren Studien mit dem Vertrauen fortsetzen
kann, dass er sich in dem VValde der organischen Chemie
nicht mehr verlieren wird."
Such a statement from a man so high in authority certainly
carries with it considerable weight even in an age when the belief in
authority is supposed to have been shuttered, at least in scientific
circles. But even Ostwald's ex cathedra statements must be taken
cum grano salis. An author who in writing his "Grundlinien" of
inorganic chemistry falls back on a style that the Germans charac
terise as "naturbeschreibend", who apparently has no conception of
the possibilities of the enlarged periodic theory viz. that the proper
ties of substances, elements as well as compounds, are functions of
their structure, cannot be expected to have a clear vision of the
possibilities of right reasoning in the systematics of the carbon
compounds.*
Yet Ostwald instinctively Feels that Moves has taken a step in
in advance of many if not most texthook writers. Whether he has
seen the deficiencies in the authors line of reasoning seems doubtful
at least. The logic of the "peculiar" systematics of the book, there
fore, deserves a more careful consideration.
The reasons given (p. 69) for regarding the hydrocarbons
as the basal carbon compounds from which all others may be derived
by substition, are all well and good. The opportunity to affiliate
more closely the didactic treatment of the carbon compounds with
that of the less numerous derivatives of seventy odd other elements,
however, ought to have been regarded as too good to have been
missed.
To state that, according to their empirical formulas, all hydro
carbons can be grouped into "series" represented by the general
* Comp. this journal, vol. 'J'J, p. 2.'!3 et aei|.
formulas CnHa+2, CnHnn, CnH2n—2, etc., is exceedingly unfortunate.

It is but natural, therefore, that the author should find himself in
deep water as soon as he takes up the hydrocarbons of what he
designates the second series. We quote his own words (p. 96)
'"Empirically the members of the second series have the formula
CnH2n. In realty, however, there are two series which have this
formula, viz. the unsaturated ethylene or ethene series, and the
series of saturated cyclic hydrocarbons." As a matter of fact, there
are several known saturated cyclic series which come under the
formula of saturation CnH2n.
Under the next formula of saturation, viz. CnHan—2 matters are
made worse by confounding members of the acetylene series with
those of the diene series.
Hydrocarbons of the formula of saturation CnH2n—4 are dis- ,
posed of with the enumeration of valylene (p. Ill) and a paragraph
on the terpenes (p. 117).
Under the formula of saturation CnHan —6, the benzene series is
the only one mentioned. Indeed the formula of saturation is re
garded as identical with the empirical formula of this series. While
chapter VII is devoted exclusive!y to benzene and its homologues,
the table on p. Ill enumerates dipropargyl and 2,4-hexadiin.
Less saturated hydrocarbons are disposed of under the heading
''Hydrocarbons related to benzene."
If the oversight over the hydrocarbons is marred by confound
ing the conception of homologous series with the ideas underlying
formulas of saturation, the classification of the substitution products
of the hydrocarbons is even less fortunate (pp. 153—155.)
By way of illustration. Of the monatomic alcohols of the
methane series, those up to the amyl alcohols are discussed. These
are followed, by vinyl alcohol and allyl alcohol ; these in turn by
cyclo pentanol, borneol and the phenols.
The terms primary, secondary and tertiary are defined structur
ally, evidently with reference to the definition that alcohols are to
be regarded as hydroxy substitution products of underlying hydro
carbons. The historical development of this method of nomenclature
with reference to the type carbinol apparently is not given. The
same terms when applied to amines are still defined with reference
to the type ammonia (p. 555). Certainly such confusion having
come down to us from a theory fifty years and more old, and
supposedly long superceded for purposes of classification, does not

make it easy for the beginner not to get lost in the woods of organic
chemistry as Ostwald puts it in his introductory remarks.
While the dicyclic borneol is discussed briefly (p. 179), none of
its isomers of the monocyclic terpineol group, nor the chain isomers
geraniol and linalool are mentioned. What a splendid opportunity
is here missed to give a student a truer insight into the relation of
series of compounds possessing the same degree of saturation.
Space does not permit to go into further discussions. Such errors
as the formula for triphenylmethane (p. 140) reveals are altogether
inconsequential as compared with an imperfect application of the
principles of a logical classification. Neither are the above criticisms
directed primarily against the author of the textbook. Organic
chemists have so long been bent on the preparation of new compounds
that the systematic arrangement of those already known and of
those to be prepared in the future, has been ignored by the best of
them. Besides the author also appreciates the limitations of the
average beginner in organic chemistry on this side of the Atlantic.
The protest registered in this review is directed mainly against the
author of the "Zur Einfiihruug". When a man like Ostwald pro
claims to the world that the author of this textbook has solved a
serious problem in a novel manner, he is supposed — by the thousands
of chemists who admire his work and go so far as to worship his
name — to know what he claims. That in this instance, at least he
has trodden on ground unfamiliar to him must be apparent to those
who have learned to think clearly in structural chemistry. E. K.
E. Merck's anntal report. Volume XX. 1906. A report on the

advancements of pharmaceutical chemistry and therapeutics.
Brochure, pp. \W.\.
The original German report has already received attention. See
p. 2H(} of the September number of this journal for last year. It
may suffice, therefore, to call the attention of our readers to the
fact that the English translation has since made its appearance. It
certainly redounds to the credit of modern pharmacy that even, the
reports of its business enterprises are of such scientific value that
their permanent place in the libraries of our educational institutions
is thereby assured. E. K.
FREDERICK B. POWER.
"The advancement made In pharmaceutical education in this country during
the past rIuarter of a century i> unquestionably due in large part to the Htnte
universities which have established pharmaceutical courses during that time. The
T'nlversliy of Wisconsin was the second of these universities to establish Bnch a
course. In planning the course and In placing It on a firm footing, you performed
a valuable service not only to our state, but to the improvement of pharmaceutical
education throughout the country. The value of your services here were greatly
enhanced by scientific research at a time when this aspect of university activity
was in its infancy.
"The work so well begun here has been continued in the east and abroad. The
great opportunities which you have enjoyed as director of the Wellcome Research
Laboratory you have utilized to the fullest extent.
"Inasmuch as twenty-five years have lapsed since you were appointed the first
professor of pharmacy at the University of Wisconsin, this Is an appropriate time
to recognize your services to pharmaceutical education and science. Therefore, upon
the recommendation of the faculty, and by the authority of the regents, 1 confer
upon you the degree of Doctor of Laws with all the rights and privileges there
unto appertaining."
Ststfluent made by President C. K. Van II ■ on the occasion of conferring the honorary degree of Doctor of
l.twb upon Frederick Helding Power by the University of Wisconsin, Wednesday, June IT, I9Wt
Volume 26. JULY, 1908. N'hmber 7.
Some General Observations on the United States

Pharmacopeia.
By Benj. L. Murray.
We have nil heard so much during the past few months about
the Pure Food .Law and its disastrous and beneficial effects that
even a reference to it here may at first appear to be unwarranted
as being a reference to an overdiscussed subject. However, there are
some of us, indeed it is safe to say there are many of us, who come
into such close and continual touch with that now well advertised
bit of legislation, that the recital of difficulties encountered in
endeavoring to comply with the law may not be wholly unprofit
able. It is not indeed the intention to speak directly of the Pure
Food Law itself, but of one of the works of reference set up by the
law as a standard for medicinal chemicals and drugs — that is the
United States Pharmacopoeia.
The U. S. Pharmacopoeia is a book so well known to all of us
here that it really needs no introduction ; but for the sake of clear
ness let me say that it is prepared by the most prominent men of
our country in the professons of chemistry, pharmacy, and medicine.
Eight revisions of the book have appeared, about ten years elapsing
between the revisions, the latest, the eighth, having become effective,
or, to use the words of the title page, "official" on September 1st.
1905. The Food and Drugs Act, which was passed some months
later than this and went into effect somewhat over a year later, set
up this United States Pharmacopoeia as a standard not only as to
strength, quality and purity of all the articles within its covers, but
also as to methods of analyzing and testing them. These methods
of testing, as you readily see, have become important, und some
three or four of them will be discussed.
The Melting Points of the U. S. Pharmacopoeia. The
melting points of very many chemicals furnish us excellent indexes
(193)
of their purity. A chemical that is really pure may in general be

said to have a constant, definite melting point, while a chemical
sufficiently pure for medicinal use may in general be said to have a
fairly constant, definite, melting point. Medicinal chemicals, which,
as you know, are not really pure in the strict sense of the word and
are not required to be so, may melt within a few degrees of the
temperature at which pure ones melt, say within three or four
degrees, sometimes even much closer than this. It is not possible,
however, to prepare them, especially when confessedly not entirely
pure, so that they will always, for each batch from the factories,
have exactly the same melting point. In other words medicinal
chemicals as prepared by the different manufacturers will vary
somewhat. They cannot be expected lo be always the same.
Although the Pharmacopoeia, and hence the Pure Food Law,
lays down standard melting points for many articles it does not
give any method of determining the melting points. This is a grave
defect in the book. To require us to live up to a given standard
without at the same time laying down an official method telling us
how to ascertain our position with respect to that standard, is un
just to say the least. Of course our chemistries and text-books
tench us how to determine the melting point of an article, in fact
to take a melting point is a matter of common knowledge. But it
is surprising how many different ways there are of doing the
work, and how many different results can be obtained by these
different methods of working. . There are various contrivances and
pieces of glass apparatus for use in this, work and various ways of
using these pieces. Some chemists heat the substance under examina
tion for only a short time, others for a long time, before the tempera
ture is raised sufficiently high to cause the substance to melt. Some
chemists dry the material before testing, others do not. And there
are other variations in the manner of performing the test. These
points are doubtless familiar to all here, and probably all know
that a melting point determination can be manipulated in such a
way as to vary it from two or three to even six or seven degrees.
As a good method of taking melting points, and one suitable
for adoption by the U. S. Pharmacopoeia, the following outline is
suggested. It may well be reworded and serve as a general descrip
tion to he placed in the Introductory Notes of the book with other
directions of a general nature. Reduce the sample to a very fine
powder and then dry thoroughly over sulphuric acid. Fill the
customary thin-walled capillary tube (about the size and length of
an ordinary pin), leave one end open, and attach to an accurate
thermometer so, that the sample lies right beside the mercury bulb.
This bulb must be small and have thin glass sides so that it is
easily affected by the heating and quickly comes to its correct read
ings. Use a Roth apparatus and insert the thermometer bearing
the sample through the customary perforated cork. The Roth
apparatus has perhaps some advantages over others, but at least
some particular form of apparatus should be selected and made
official. Bring the temperature up quickly to within fifteen degrees
of the expected melting point, then heat slowly, at such a rate that
the temperature rises about two degrees per minute, and so that
if the flame is removed the temperature no longer goes up. When the
powder is all, or practically all liquid, read the thermometer and
consider the reading as the melting point. For preparations that
can be heated only a very short time without decomposing, place
some glass-wool in the bottom of the wgll of the Roth apparatus,
insert the thermometer with a doubly perforated cork and heat
to within two or three degrees of the expected melting point.
Through the second perforation of the cork and without removing
the thermometer, drop a capillary tube containing the sample on
to the glass-wool at the bottom of the well and close beside the
thermometer. Have several capillaries filled and ready, so that they
may be dropped in one after the other as the temperature slowly
rises, until one of them melts within a minute after its introduction.
This gives the correct melting point.
Notwithstanding the fact that different lots of medicinal chemicals
will show somewhat varying melting points even under the best
conditions, and different chemists, unless restricted, will use different
methods, the Pharmacopoeia is at times very exacting in its require
ments. In some cases the text does not allow even one tenth of a
degree leeway or deviation. The absurdity of such requirements is
evident, especially when we remember that the Pharmacopoeia (not
by inference) but by direct statement allows as a normal constituent
varying amounts of water in many preparations. How then under
such conditions can one make sure that his goods conform to the
U. S. Pharmacopoeia and hence to the Food and Drugs Act?
There is perhaps nothing especially new in these suggested
methods of determining melting points. It is desired in this con

nection, however, to emphasize the need of some good method in
the Pharmacopoeia.
The Boiling Points of the U. S. Pharmacopoeia. Much
that has been said of melting points applies with equal force to
Boiling Points. Boiling points are good indexes of purity; they
vary with different batches of medicinal chemicals and with the
many different ways of determining them. Here again the Pharma
copoeia gives too close figures, and at the same time fails to provide
us with a standard method of arriving at those figures. A general
method for the determination of boiling points should be found in
the Introductory Notes of the book along with the other general
statements.
The boiling points of the Pharmacopoeia are not as yet defined
by the book, but the intention in general seems to be that the
boiling points are the temperatures at which complete distillation
occurs. For example Benzin is stated as having a boiling point of
45 to 00° C., meaning presumably that it all distills between these
temperatures. Since the pharmacopoeial chemicals are admittedly
not pure, this style of boiling point should be adopted throughout
the text; that is an upper and lower limit should always be given.
Such is not always the case at present.
A method of determining boiling points that has been found
reliable in the hands of many chemists and applied to many chemi
cals may be outlined here. It is suggested as a good basis for a
general method to be used in connection with the next revision of
the Pharmacopoeia.
Select a side-arm distilling-flask (a fractionating-ilask) with plain
neck (not bulbed), having the side-arm about two inches above the
bulb part of the flask. Fill the flask approximately two-thirds full
of the material under examination and insert the thermometer so
that the top of the mercury bulb is about half an inch below the
side-arm of the flask. This thermometer should of course be selected
for small thin bulb so that it is easily affected by small changes in
temperature and quickly comes to the correct readings. After con
necting with a suitable condenser heat the flask carefully by means
of a small flame held in the hand and passed to and fro under the
bare bulb of the flask. The flame should generally be only about
an inch long and is best when semi-luminous or luminous. This
may be obtained by partly shutting off the air on a small Bunsen

burner and turning the gas low. Sometimes it is advisable even to
black the bottom of the flask with the flame as the heat is better
distributed in this way. Continue to heat in this same manner, with
the flame in the hand until the distillation is finished. Of course at
the beginning some time must be allowed for the thermometer to
adjust itself, and naturally care must be taken not to overheat the
material, but such points must be watched in all methods of doing
the work.
The above process or some other good process definitely laid
down in the Pharmacopoeia would very materially help us who are
striving to comply with the requirements of the U. S. Pharmacopoeia
and hence the requirements of the Food and Drugs Act.
Other Requirements of the U. S. Pharmacopoeia for
which no Method is given. Our present Pharmacopoeia
abounds in Purity Rubrics. In fact it almost exults in them. It
looks fine at the beginning of the description of a preparation to
see "It t-hould contain not less than 99% by weight of absolute
acetone", or "not less than 99% of pure Potassium Ferrocyanide",
or "not less than 99.5% of pure Zinc Phenolsulphonate", or "not
less than 99.9% of pure metallic mercury". Such is the language
of Purity Rubrics and these are actual quotations from the text.
But what two chemists could agree on the analysis of these articles
when, as at present, each has his choice of methods by which to test
the goods, and when, as may easily happen, one chemist is anxious
to get high results, while the other hopes to get low? There are
many cases in the Pharmacopoeia where a glowing Purity Rubric is
given, but no corresponding method of analysis is to be found in
the text. After performing all the tests that are in the Pharma
copoeia, on mercury for instance, we still have not made sure that
the mercury is of U. S. P. quality. It must still be ascertained that
it is at least 99.9'/<. Not all of us are able to agree with ourselves
even in duplicate analyses to the tenth of a percent, especially when
working on mercury. U. S. P. Mercury, by the way, is one of those
articles with a wonderful boiling point. It must boil at 357.25° C.
Here we have it to the hundredth of a degree. Purity 99.9%; boil
ing point 357.25'/;° C.!
Why do we impose such severe and unnecessary restrictions upon
ourselves? We owe it to the consumer and producer alike, in fact
to all within the purview of the law to drop such purity require
ments from our book of standards, or to insert suitable and cor
responding methods of testing. If there are no suitable methods of
testing, why make such purity requirements? They are useless. And
if there are suitable methods of analysis why not have them in the
book?
The Residues of the U. S. Pharmacopoeia. There are
many places in the Pharmacopoeia where, after directions are given
for carrying out evaporations or ignitions, use is made of the
expression "No residue should remain", or, "No appreciable residue'':
or "No weighable residue". These expressions "'no residue", "no
appreciable residue", "no weighable residue" are very loose, and,
being susceptible of different interpretations, are undesirable. As a
rule medicinal chemicals do not need to be of such exceptionally
high quality that no residue, or uo weighable residue in the strict
sense of these terms shall be found in the various tests in question.
It is furthermore evidently not the intent of the Pharmacopoeia that
these terms should be taken in their strict sense; and it is really on
this account that some definition of the terms should be incorporated
in the text.
It is here suggested that a definition of the above and similar
expressions be given among the general statements in the Intro
ductory Notes of the Pharmacoptpia. Let them be defined as mean
ing residues weighing up to 5 milligrams.
The Specific Gravities and Solubilities of the U. S.
Pharmacopoeia. Speaking in general it is a fact that all the text
books of the world, all the chemistries, all the pharmacopoeias, all
chemical journals etc. base their specific gravity and solubility
figures on the temperature 15° C. Practically all our tables of
specific gravities that have been worked out by so many years of
experiment, by so many scores of chemists, are based on a tempera
ture of 15° C. The great hosts of solubility figures in chemical
literature are as a rule based on experiments made at 15° C. But
on September 1st, 190.">, when the present edition of our Pharma
copoeia went into effect, we of the United States put behind us all
these valuable data collected by years of previous patient work on
the part of ourselves and others, and launched out on a separate
career of our own at 25° C. In other words the U. S. Pharmacopoeia
directed that in general all specific gravities be taken at 25° C.
PHARMACEUTICAL REVIEW. 19!)
compared with water at 25° C. ; and that all solubilities be taken

at 25° C. This one change brands our Pharmacopoeia with an un-
mistakeable air of provincialism.
What was the great advantage gained by the adoption of 25° C.
instead of the world-wide-accepted and time-honored 15° C. ? There
must have been some decided improvement or advantage in the
minds of the Committee of Revision of the Pharmacopoeia when this
change was introduced, for its introduction entailed a great amount
of work. Only one reason, or excuse as it may be called, for the
change has ever come to my notice. It has been stated that 25° C.
is nearer the average room temperature than 15° C., and consequently
it is easier to work at 25° C. But if one is an accurate worker he
will find it is necessary to use artificial means to maintain a tem
perature of 25° C. throughout a test, the same as he would to
maintain 15°. It is seldom indeed that the room temperature is
just 25° C. And if one is not an accurate worker he might just as
well work at 15° as at 25c, for he will really maintain neither tem
perature.
To be really frank, none of the advantages obtained by changing
over to the 25° basis on our specific gravities and solubilities has
ever become apparent in continuous application of the new standard
since the day of its adoption. But some of the disadvantages have
come to light. The greatest disadvantage is probably the loss of
the use of the immense amount of data stored away in literature
and based on 15° C. Generally speaking when we have tnken our
solubility or our specific gravity at 25° C. we cannot compare our
figures with those of other chemists, because other chemists state
their results at 15° C. We lose the use of their figures. If we read
in our journals or reference works that an article dissolves in ten
parts of water, we cannot compare that with the statements of our
book of legal standards, the Pharmacopoeia, because the one state
ment is based on 15° C. and the other on 25° C. We lose the use
of our literature. Not only are we depriving ourselves of many use
ful data, but we are actually adding confusion to chemical and
pharmaceutical literature already none too clear. For these figures
of our Pharmacopoeia based on 25° C. are finding their way into the
pharmaceutical, medical, and chemical literature, but without
the distinguishing 25° attached to them; so that, when
one now sees a specific gravity or solubility stated, doubt
alwaysarises as to which temperature forms the basis of the

figures.
No other branch of chemistry besides U. S. P. chemistry has
inclined to the new standard. Apparatus standardized or graduated
at 25° C. is practically unknown, and is to be had only at prohibitive
prices, because it is all made to order. There is no demand for it,
a fact which in itself is a good indication of how well the idea of
working at 2f>° C. finds favor with practical chemists. It was an
unwise move on the part of the Committee of Revision of the
Pharmacopoeia to change to the 25° basis and it has already been
requested of them that they restore our standards at 15° C. As a
compromise it hos been suggested to the Committee that figures be
given both at 15° C. and at 25° C., the 15° for the use of us of the
old school, and the 25° for the advance guard, or for those who
prefer it.
As a summary of these pages it may be said that practically all
in pharmaceutical and chemical lines are endeavoring to comply
with the requirements of the Pure Food Law, and that means in a
large measure complying with the requirements of the Pharmacopoeia.
Let us, therefore, help this movement along and at the first oppor
tunity revise and correct some of the shortcomings and inconsistancies
that run through the text of our Pharmacopoeia from beginning to
end to such an extent that they are general in their nature.
Pharmaceutical Pot.
Keber Collection.
Literature on Medicinal Plants and Drug Plant Culture*
By Albert Schneider.
An attempt has been made 'o cite the more important literature
treating of the occurrence, distribution, use and cultivation of
medicinal plants, especially those found in the State of California.
While some citations on the chemical investigations of drug plants
are given, no attempt has been made toward completeness in that
direction. Such citations would be of inestimable value to investi
gators and it is hoped that some one may have the time and the
opportunity to complete such a task.
It was tought desirable to include a few citations, which do not
refer to medicinal plant culture directly. There is, for example, an
extensive literature on fertility of soil, chemistry of soil, seed testing
and selecting, plant physiology, tilling of soil, etc., which is of more
or less importance to those who desire to enter upon the more
intelligent consideration of drug plant culture. In some instances
the publications are abstracted very briefly : others are not ab
stracted, as the title is sufficient to indicate the nature of the subject-
matter. After consulting the literature here cited, those interested
will no doubt be able to obtain additional literature and to secure,
through other sources, additional desirable and necessary informa
tion. The Department of Agriculture at Washington, The California
State Horticultural Society, The College of Agriculture of the Uni
versity of California, the California Promotion Committee of San
Francisco, and the Boards of Trade of towns and cities are willing
and ready to give information in so far as it is possible.
Most of the references to the literature having a more direct
bearing upon the plants mentioned, will be found with the plant
descriptions published in The Pacific Pharmacist. This also includes
* This paper i* suppl(?m»ntary to the series ot papers on Tbe Native asd
IXTBODITCBD PolSOMOt'S AND MEDICINAL PLANTS OF CALIFOKNIA, HOW being published
in the Pacific Pbarmac ist (begun May, 11)07). It is published entire in this issue
as in this form It can be used more conveniently. Though a supplement, as stated
above. It Is nevertheless quite distinct and will no doubt prove ol value to inter
ested parties in other states and territories of the Union.
theses prepared by the students of The California College of Pharmacy.

Most of the special information, such as range and distribution,
morphology, etc., regarding California medicinal plants, will be found
in the special California publications, as Zoe, Erythraea, Pittonia,
the Proceedings of the Academy of Science, the Geological and
Railway Exploration Reports, the Ethnolooical Reports and
Government Expedition Reports. These may be consulted in the
various libraries of the state, as at Sacramento, State University of
California, Leland Stanford University and at the California Academy
of Science. There are also various California floras, published by
well-known botanists as Jepson, Coulter, Behr, Watson and others,
which may be consulted by those interested. It will also be found
that the literature on the introduced medicinal plants of California
soon merges into that of the neighboring states and territories,
Mexico, Australia, .In pan, and other countries. Many plants are
being introduced from the Philippine Islands and the West Indies.
Those desiring further limited information on the morphology,
chemistry, physiological action, uses, etc., of many 'of the plants
mentioned, are advised to obtain a copy of some Dispensatory
(National or King's) or some standard text-book on pharmacognosy
(Culbreth, Say re, Maisch, Wall), always specifying the latest edition.
The National Dispensatory is allopathic while King's Dispensatory
is eclectic. Of the text-books on pharmacognosy, Culbreth's and
Sayre's are perhaps the most complete in many ways, and the
former is quite up to date on nomenclature.
The intelligent use of the subject index to the literature will
make it possible to collect quickly a nucleus to the literature on the
history, range and distribution, chemistry, properties, cultivation,
etc., of the plants mentioned. Two almost indispensable publications
treating of medicinal plants are The Proceedings of the American
Pharmaceutical Association and the American Journal of Pharm
acy. Most of the references are made to these publications. There
are complete sets in the library of the California College of
Pharmacy, San Francisco.
Citation of Literature in Alphabetical Order by Authors.

(1) C. S. Andersox. List of California Marine Algae with notes. Zoe.
2, pp. 21 T—225. 1 89L
12) ('. Andrews. Areeu nuts. Proc. A. Ph. A. (aba), 23, p. 128. 1875.
(3) Annual Reports, Board of Pnrk Commissioners of San Francisco.
(Thirty-Ant Rep. 1904.)
(4) J. J. B. Abgenti. The Olive and its Product, Proc. Calif. Pharm.
Soc. 1881. (Abstract.)
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(225) J. M. Maisch. Sneezeweed. Proc. A. Ph. A., 20, 233—230. 1872.
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p. 136. 187."..
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1893.
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(To be continued.)
Plant Pigments.*
I»y /. W. BraiuM.
Martens,27 who adopted the theory of Fremy and Cloez in 1855,

traced the origin of xanthein back to a light yellow plant juice
which the plant formed in the parenchyma cells. By the action of
light and alkalies, it takes up oxygen becoming more and more
yellow. This "Extractivstoff" by further change and subsequent
uniting with fatty substances produced the different yellow pigments
of leaves and flowers. These yellow pigments by the continued
action of light and oxygen are changed to red. Cyanine is the pig
ment in blue flowers and is generally accompanied by traces of yel
low pigments.
Phipson,2s 1858, extracted a substance from the wood of Rham-
mis frangnla which he called rhamnoxanthine. This substance had
similar properties to xanthophyl, the yellow pigment in fall leaves,
but is probably not identical with it. Yellow leaves when dipped
into sulphuric acid become emerald green, continued action turning
them yellow or brown. Rhamnoxanthine acts in the same way and
therefore may be the pigment found in some leaves.
In 1859, Hochleder20 isolated the glucoside quercitrin and its
product of hydrolysis, quercetin from the flowers of a number of
plants. The flower buds did not contain these substances and he
assumed, therefore, that they were formed in the flowers. The author
attributed the yellow color of the specific flowers examined to the
presence of quercetin.
In the same year, Hlasiwetz30, as a continuation of Rochleder's
work, made a detailed chemical study of quercetin. From the results
obtained he devised a general theory of plant pigmentation. Upon
heating quercetin with caustic potash, he obtained phloroglucin and
• Continued from page ISO.
« Jahreab. u. d. Fortschr. d. Chem., 8, p. 657.
»» Compt rend.. 47. p. M12.
»• Journ. f. prakt. Chem., 77, p. 8*
3° Journ. f. prakt. Chem., 78, p. 23 7.
21 0 PHA KMA CE VTICA h KEYI EW.
a substance which was called quercetinic ai-id. Accordingly, yellow

flowers owe their color to quercetin. The fact that some yellow
flowers turn red is explained by assuming that quercetinic acid is
formed which is colored red in the presence of alkali and oxygen.
Quercitrin, the glucoside of quercetin, gives a brown color in the
presence of alkali and oxygen. Quercetinic acid in the presence of
iron oxide gives a blue coloration and a mixture of red and blue
would explain the presence of violet. The author regrets that the
amount of pigment in the flowers is so small that these compounds
could not be isolated from the flowers directly.
Stein.'" isolated from the flowers of Sophora japonica, Leucojucn
vernum, Acer psmido-platamts, and Cornus mascula, a substance
which was identified with rutinic acid or rutin, first isolated from
the herb of Hutu gmveoleus by Weiss.1i-' Because of its occurrence
in so many other plants besides the one from which it obtained its
mime, Stein called it ;Pflanzengelb\ 'Phytomelin' or simply 'melin'
(from Greek /irjXtvns, Quittengelb).
By some melin was supposed to be identical with quercitrin.
I'pon careful study, however, Stein found the two substances to be
different although upon hydrolysis both yielded quercetin. The quer
cetin from melin, Stein called meletin. l'pon reduction with sodium
amalgam, melin as well as meletin yields a red substance called para-
carthamin. This compound was made the basis of his theory or plant
pigmentation. Many red flowers upon treatment with alkali become
green thus behaving as does parocarthamine in the test tube. The
flowers in the bud contain meletin and are therefore yellow, but
become red as the meletin is changed to paracarthamine. The pig
ments of blue flowers are compounds of the red pigment paracar
thamine with weak bases. Thus the pigment in the blue flowers of
Centuureu cyauns, is supposed to be the calcium derivative of para
carthamine.
According to W'igand8a, 1862, tannin plays a very important
role in the chemical processes which take place during the life of a
plant. For example, the unripe fruits are rich in tannin content
which decreases upon the ripening of the fruit at the same time that
the sugar content increases. The tannin, therefore, is supposed to
*i .Journ. f. prakt. Chem., 85. p. 351,
a-' Pharm. fVntralhl.. 1S+'2, p. it08.
33 Itot. Ztg . 20, i>. 121.
PHARMA CEVTICA L REVIEW. 217
be changed directly into sugar. In t he same way all red and blue
plant pigments with the exception of indigo and a few others are
supposed to be derived from tannin by very slight changes, as is
shown by the fact that the pigments have almost the same chemi
cal properties as tannin ami can very readily be eluuiged back to it.
Many of the natural red dyestuffs are not found in the plant as
such, but as a colorless substance which is changed by the action of
air or alkalies to the red dyestuff. This colorless substance the
author calls, cyanogen and thinks it closely related to tannin lo
calise of its behavior towards chemical reagents. Furthermore this
cyanogen is only found in tannin-containing plants and only in
those cells which originally- contained tannin.
The red leaf pigment he regards as in no way related to chloro
phyll; for either the two pigments are found in different cells or, if
they are found in the same cell, the red pigment is dissolved in the
cell sap while the chlorophyll is found in the form of granules. This
red leaf pigment originates again from a colorless substance which
is supposed to be identical with tannin for the following reasons:
1. The red coloration of leaves is found only in such plants as
contain tannin.
2. The red pigment is found only in those cells which have pre
viously contained tannin.
.'{. The red cell-sap gives the same green or blue color when
treated with ferric salts as does tannin.
The red and blue colors of flowers according to his interpretation
are directly due to the presence of anthocyan which is an oxidation
product of tannin. This assumption depended merely upon the fact
that blue and red flowers are decolorized by reducing agents like
sulphur dioxide and that white flowers become red when treated
with acids.
Sorby"4 in 1871, divided all plant pigments into five groups.
T. Chlorophyll Group. Chlorophyll is not a single substance.
Different plants contain different chlorophylls. The leaves of most
plants are colored green by a mixture of two or more kinds of
chlorophyll. Some kinds of chlorophyll are turned blue with hydro
chloric acid : others are not.
It.' Xanthophyll Group. To this group belong the yellow pig-
« Chem. N'ewa, 2H, pp. 137, 148.
ments of leaves and flower.-) insoluble in water but soluble in alcohol

and carbon disulphide.
Ill Erythrophyll Group. This contains the red pigments. These
pigments are of various degrees of red, their color is intensified by
acids and turned to blue or green by alkalies. These red pigments
form colorless solutions with alcohol and leave a red residue upon
evuporation.
IV. Chrysophyll Group. These are golden yellow pigments
soluble in water and insoluble in alcohol and carbon disulphide.
V. Phaiophyll Group. To this group belong the brown pig
ments.
In as much as in the explanation of the fall coloring of leaves,
the same sort of reasoning was applied as was often times used for
flower pigmentation, Sorby's explanation of the fall coloring of
leaves will not seem out of place here.
The endless variety of autumnal tints of leaves he regards as
commonly due to varying mixtures of pigments, belonging to two
or more of the above groups. Unfaded green leaves are colored
mainly by chlorophyll, but the tints are modified by colors of the
xanthophyll and chrysophyll group. This explains why we find
varying shades of green in different leaves. On shaking an alcoholic
extract of a green leaf with carbon disulphide, the chlorophyll will
be removed leaving the xanthophyll in the alcohol. This chlorophyll
has a much brighter green color, than the leaf had. The presence
of pigments of the erythrophyll group produces brownish tints. If
erythrophyll preponderates over the chlorophyll we have red
or even purple-green as in the case of copper-colored and purple
beech leaves. In autumn, the chlorophyll decomposes leaving the
xanthophyll or erythrophyll. Thus the yellow color of faded leaves
is due to the xanthophyll and the red color to the erythrophyll
which previously existed in the leaf, the alteration in color consist
ing merely in the disappearance of chlorophyll.
Kosolla5, in 1884, isolated a yellow coloring matter from the
flowers of Helichrysum bracteatnm and Helichrysum arenarium which
he called helichrisin. This is a yellow amorphous powder which gives
red derivatives with the heavy metals and forms blue solutions with
both acids and alkalies. The author believes it to be a quinone
as Monatah. f. Chem., 5, p. .
like compound, because it is easily declorized by reducing agents.

The color of the flowers is supposed to be due to helichrysin or its
derivatives.
In as much as the phenomenon of color is a physical manifesta
tion, the physical study of the subject of plant pigmentation readily
manifested itself. Much of the work of determining' the pigments in
a flower was done, both by chemist and botanist, by determining
the absorption band in the spectrum. Thus Hansen"6 in 1NH4 says
that all yellow flowers owe their color to the same yellow pigment
which on account of its similarity to animal lipochromes, he calls
flower-lipochrome. All red flowers owe their color to the same red
pigment. This is determined by the fact that most red flowers give
the same absorption bands in the spectrum. The blue and violet
pigments are derivatives of the red pigments. By the action of acids,
the blue pigment turns red. The spectrum of the blue pigment,
turned red by acids, is the same as the spectrum of the pigment of
flowers which bloom red.
By treating a mixture of phenol and ammonia with hydrogen
peroxide, Wurstera7 obtained a blue solution which gradually became
green and then yellow and finally with an excess of hydrogen
peroxide the solution became colorless. Upon the addition of acids,
the blue solution turned red, from which solution Wurster isolated
phenolquinoneimide, first prepared by Hirsch.a8 Wurster noticed the
similarity of the behavior of this compound to that of red and
blue flowers and suggests it as a possible explanation of plant pig
mentation, although he had not isolated a quinoneimide from a
single flower.
Hydrogen peroxide is formed in a greater or lesser quantity
during the life process of the protoplasm. Hydrogen peroxide can
be easily identified in the juices of many plants, also in flowers and
seeds. Therefore, in the presence of ammonia and a phenol, which
occur so widely distributed in the vegetable kingdom, a phenol
quinoneimide could be formed. Thymol and other phenols found in
plants readily form the corresponding quinoneimide. Resorcin, when
heated with ammonia and hydrogen peroxide gives a blue solution.
Resorcin when melted with quinone gives upon the addition of
ammonia, a deep green solution. Upon shaking this solution with
a• Hot. Centralbl.. 20, p. a6.
st Ber. 20, p. 2984.
•» Ber. 13, p. 1909.
220 rH A KMACE UI'l CA L KE VIEW.
air, it gradually turns yellow, then red and finally brown. Wurster
compares this color changes to the color changes which some leaves
undergo as for example the Berberts species. Nothing is said, how
ever, about the occurence or the source of the quinone necessary for
these changes.
In 189.S, Nienhaus88 attempted to explain the formation of violet
pigments, by assuming the formation of carbaminic acid from the
ammonia and carbon dioxide of the air. He says the changing of
red pigments to violet is not an oxidation process as is sometimes
thought. The red flowers of Papaver rhoeas when dried in the air
always turn violet. By drying them in an atmosphere absolutely
free from ammonia, the flowers retain their red color.
From this survey of the theories which have been advanced as
so many attempts to explain the various color phenomena in plants
it will readily be seen that nothing satisfactory has been accom
plished.
With the exception of one or two cases, no definite compound
had been isolated. The theories are mostly based on flower extracts
which at best are complex mixtures and to which practically each
author gives different names. Even in those instances in which a
theory was based upon a definite chemical compound this, as a rule,
was not isolated from plants. The explanation of plant pigmenta
tion consisted solely in a comparison of the color of flowers with
the colors produced by the action of different chemical reagents upon
this compound.
On the other hand, in those few instances in which a definite
plant constituent was made the basis of a theory, chemical changes
were assumed to take place which could not be definitely explained.
Nothing was known of the nature of the resulting product except
that it was colored.
{To be I'antiuned.)
PllARMACELTICAL REVIEW. 221
Literary.
Books Reviewed.
Comment epurer sox eau. Par Dr. F. Malmejac. Vigot Frores,
editeurs, Paris. Un volume in — 16 cartonne. Pp. vin, 210,
avec 12 figures. 1907. Kr. 3.50.
The average chemical student, who early in his course learns to
write reactions involving the action of acids on bases, finds that
Hi>0 is so common a factor in these equations that he soon begins
to ignore it. He is taught to emphasize the affinity between acids
and bases so that the affinity of hydrogen for oxygen, as indicated by
the thermo-chemical equation of water, is practically overlooked.
Difficulties of a structural nature he learns to brush aside by speak
ing of water of crystallization, water of hydration, cryoscopic water
etc. And yet in this world of ours, whether we view it from a chem
ical or a biological point of view, water is an all-important factor.
It is but comparatively recently that from an hygienic point of
view, man has begun fully to appreciate the significance of pure
water. We now insist that at least the place in which we live has
an abundant supply of pure water and even insist that others in
our community refrain from the use of impure water because of the
indirect danger to ourselves. To accomplish this has been no easy
task and the work has been but partly done thus far. There are
still too many cities where the drinking of water is accompanied
with grave danger.
The author has written his little treatise on "How to purify
your water" not so much from the point of view of the sanitary
engineer as from the point of view of the individual who desires to
help himself. He reports on the numerous methods that have been
suggested for the purification of water, especially on a small scale,
and recommends those which he regards best both at home and
while traveling. For those who desire to make a more detailed
study of certain aspects of the subject, a bibliography of over one
hundred articles and books has been added. To pharmacists this
book ought to prove very useful, for he is frequently asked for ad

vice by customers who desire to purchase the necessary chemicals.
E. K.
ARBEITEN AUS DEM PHARM AZEUTIBCHEN INSTITIT DEB U.MVERSITAET

Berlin. Herausgegeben von Dr. H. Thoms. Vierter Band,
umfassend die Arbeiten des J ah res 1906. Pp. MO, mit 10 Ab-
bildungen und 6 Tafeln. Urban & Sch warzenberg, Berlin.
11)07. M. 7.00.
The fourth volume of the "Arbeiten" contains a new feature
which is designed to make this annual more popular with the
pharmaceutical practitioner. About thirty pages are devoted to a
review of the more important new remedies introduced during the
year 190(1. This review is followed by more detailed accounts of
the investigations of ten new remedies and fifty-flve secret prepara
tions. Nearly one-half of the volume is devoted to reports of this
nature. The Berlin Institute is performing a valuable service to phar
macy, a service that is appreciated not only by the pharmacists of
Germany but on this side on ths ocean as well. For this reason
alone, the "Arbeiten" should find a place in every college library.
A bit of information that will prove of special interest to
American pharmaceutical teachers will be found in the published
course of studies pursued at the Pharmaceutical Institute at Dnhlem
A special feature of the "Arbeiten" for 1906 is the report on the
cultivation of poppy and the production of opium. E. K.
Squibb's Materia Medica. 1908 Price-List. A complete alphabetical

list of the Squibb products, embracing the articles in the
U. S. P. (VIII. Revision) and the National Formulary together
with the non-official chemicals, pharmaceuticals, tablets and
newer remedies in general use, setting forth their origin, Latin
and English titles, synonyms, physical and chemical character
istics, incompatibilities, antidotes, therapeutic indications,
doses, etc. Published by E. R. Squibb & Sons. New York.
1908.
Fifty years of service to American pharmacy and medicine is a
record of which any firm may well be proud. The name Squibb for
many years wa.s an asset the value of which was, no doubt, fully
appreciated by the members of the firm. However, our age is too
PHARMACEUTICAL REVIEW. 22:)
democratic and the rising generation of physicians is becoming too

scientific to he charmed by a name only. This fact also is being
recognized.
While this small volume, which commemorates in a way the
fiftieth anniversary of the firm, is possibly not such as Dr. E. It.
Squibb himself would have compiled, it is not only scientifically
modern but, on the whole, in harmony with the best traditions of
the firm. With the title page reproduced above it does not seem
necessary to state anything more about the contents than that they
will undoubtedly prove useful to many a pharmacist. We desire,
however, to call attention to the tribute paid Dr. Squibb by Professor
J. U. Lloyd. Those who know about the relation of these two men
to each other will think all the more highly of both because of this
appreciation penned by one of them. E. K.
The newer remedies including their synonyms, sources, tests,

solubilities, incompatibles, medicinal properties and doses as
far as known, together with such proprietaries as have similar
titles. A reference manual for physicians, pharmacists and
students by Dr. Virgil Coblentz, Professor of Chemistry in
Columbia University, Department of Pharmacy. Fourth edition
revised and enlarged. One vol., pp. 133. The Apothecary
Publishing Co., Boston. 1908.
Such is the multiplicity and growth of the new remedies soealled
that we welcome practically everything that offers aid to the seeker
after knowledge in this particular field. The fourth edition of the
well known "The newer remedies'' appears practically as a reprint
of a series of articles from the "Apothecary". We regret to notice,
however, that the increase in the number of new remedies has lead
to a diminution in the information which, in previous editions,
seemed already reduced to a minimum.
To a person who does not devote the major portion of his time
to this subject, the work of compiling information on secret
proprietary preparations as well as on new soealled synthetic
remedies, must at times prove a rather hazardous task. That even
a man like the author of four editions of a standard book on this
subject should make mistakes need not surprise anyone who has
tried his hand at this sort of enterprise. It may, however, ocassion-
ally vex the pharmacist who 1ms come to rely on sucIi a compilation
22+ PHA IMA CEUTICAL REVIEW.
for ready information. Thus e. g. in the very first column of page

one we find "Acet amido-solol. Synonym for Solol." To a person
who knows v hat solol is this bit of information seems a bit strange.
When next we look for solol we do not find it. We do, however,
find "Solol-acet-amidat" and are informed that it corresponds to
"Salophen" which, in turn, is ''Acetyl-p-amido-solol." If for further
information on the vexing solol we look under phenyl salicylate we
are here likewise informed that this is solol as we naturally expected.
All of this reveals anew the necessity of a central bureau, as it
were, on new remedies from which we may expect the greatest
accuracy attainable as well as thorough knowledge of the subject.
The latter alone is not sufficient in the compilation of such a
catalogue. Nevertheless we have no doubt that Coblentz' "The
newer remedies" will continue to do good service for the average
pharmacist until something more in accord with our ideals will be
attainable. E. K.
Pharmaceutical Pota.
Keber Collection.
Volumb 26. AUGUST, 1908. Number 8.
Editorial.
During the past half year the Food and Dairy Commission of
Wisconsin has given the druggists of this state an object lesson
in the enforcement of pure drug legislation. In thirty-eight
cases of prosecution all but one resulted in convictions. The one
exception is possibly as little credit to justice as the thirty-seven
convictions are a credit to pharmacy. The usual concomittant to
such prosecutions, viz. expressions of indignation on part of some
members of our calling, were not wanting. Indeed, for a lime it
seemed that the annual meeting of the State Association might be
made the scene of a demonstration against the Commission.
However, to the credit of the pharmacists of Wisconsin it must
be said that possibly there never has been a body of men who took
their own medicine with a finer sense of justice towards those whom
— for such is human nature — they might have regarded with a feel
ing of animosity or at least with a sense of resentment.
To the credit of the Commission it must be said that its chemist
was exceedingly careful in the choice of the preparations to be tested
nnd the commissioner considerate in causing prosecution in such in
stances only where there seemed absolutely no alternative. Out of
1496 samples examined by the chemists of the Commission 853 or
57 per cent were found deficient when compared with U. S. P. stand
ards. If it be remembered that the Commission prosecuted in only
thirty-eight instances, it must become apparent to even the most
critical that it was not sensational wholesale prosecution that
prompted 'the state officials. If it further be remembered that the
chemist of the commission made a report a year ago in which he
pointed out that in 493 instances of preparations examined 355, or
72 percent., were found wanting, the Commission can not be accused
of not having given the druggists sufficient warning.
It muy be said in addition that the conditions are general, us is
shown by the chemist's reports and that the comparatively few
(22.-,)
PllA KMACE V Tl CA L RE VIEW.
druggists who where prosecuted were no worse than the majority of

their colleagues. Hence the victims were unduly punished. Such
sort of reasoning will pervert nil justice if admitted. The officers of
the law are not expected to catch all offenders before sane public sen
timent permits the prosecution of one. Bearing in mind the condi
tions that have prevailed for generations past we may sympathise
with the individual, but we should not allow our sympathy for a
personal friend to lead us astray and to become unjust toward the
public servant who has merely done his duty and who, honor bound,
could scarcely have acted otherwise.
History is supposed to teach us, but, unfortunately we are, as a
rule, so unwilling to learn from the records of past experiences. It
seems as though we invariably have to go through the costly school
of experience before we are willing to learn. However, if we but
profit by our own experience our case is far from being hopeless.
Not only did the druggists assembled in annual convention at Eikart
hake show a willingness to learn, they went a good step farther,
they expressed a desire to be taught.
Such a spirit calls for cooperation and those who are in position
should gladly extend the right hand of fellowship. Dr. Fischer has,
therefore, kindly consented to place not only his figures but his ex
perience as well at the disposal of the readers of this journal.
In this number will be found the first of a series of articles on
those preparations that have been found wanting. Wherever the
writer fails to make himself fully understood or where additional
information is desired, he will be pleased to receive communications
from druggists who are interested.
PHARMACEUTIC* L REVIEW. 227
Deficient Drugs and Galenicals.
By Meharil Fischer.
I. The Deterioration of Spirit of Nitrous Ether.

During the investi" ution of the condition of the Wisconsin retail
drug market curried on during the last year by the Wisconsin dairy
inxl food commission, 14.S samples of spirit of nitrous ether were
purchased from about that number of drug stores. Upon analysis,
only eight, or 5.4'/< of the total number, were found to contain 4%
or more of ethyl nitrite; twenty-six (17.5'/;) were between three-
fourths and full strength; fifty-four (36.5%) were between one-half
and three-fourths strength ; thirty-three (22.3%) were between one-
fourth and one-half strength; while twenty-seven (18.2%) were less
than one-fourth strength, several containing no measurable amount
of ethyl nitrite. An investigation of the causes for these conditions
• showed the deficiency in most cases, and in all of the most ones, to
be due to the use of dilute alcohol in the manufacture of the pre
paration, as low as 4.09< of alcohol being found in one of the
samples which contained no measurable amount of ethyl nitrite.
Other causes for the poor quality of some of the samples were age
and faulty methods of storing.
Spirit of nitrous ether of the eighth decennial revision of the
U. S. P. is a solution of ethyl nitrite in official alcohol, yielding,
"when freshly prepared," and tested by the official assay process,
not less than 4.0% of ethyl nitrite. While the words "when freshly
prepared" were perhaps inserted into the definition to prevent a
preparation, properly prepared and stored, but containing a trifle
less than 4.0'/ of ethyl nitrite, from being pronounced unlawful, it
can hardly be considered the intention of the committee of revision
to have such a preparation still considered official after it has lost
all or nearly all of its ethyl nitrite, and perhaps on that account
these words are omitted in the text of the assay process. The in
sertion into the next revision of the pharmacopoeia of a minimum
standard of ethyl nitrite, below which no spirit of nitrous ether must
be dispensed for medicinal purposes (as in the case with other pre
parations even though liable to deterioration; e. g., ammonia
water) would be a decided improvement.
Spirit of nitrous ether prepared according to the directions of
the U. S. P. will contain very nearly 1 x$]00 = 4.557c of ethyl nitrite.
When prepared from the socalled "concentrated nitrous ether" of
the market it is probably slightly weaker but still above 4.0% pro
vided the "concentrated nitrous ether" was of good quality. The
loss of strength upon keeping is due either to volatilization of the
active constituent or to its chemical decomposition. Since the boil
ing point of ethyl nitrite is 18° C. evaporation even from its alcoholic
solution takes place rapidly unless kept in well-stoppered containers
in a cool place, as directed by the IJ. S. P. The storing of the
spirit in partly-filled carboys or in large "white-glass" shelf bottles
at ordinary temperatures is certain to cause rapid deterioration,
yet is the common practice of pharmacists. The best way of pre
serving spirit of nitrous ether is to make it up in small quantities and
keep it in small, well filled, dark amber-colored, well stoppered vials
in a refrigerator. Unfortunately few pharmacies have refrigerators
for the storage of such substances and preparations as should be
kept, in a cool place, being in this respect far behind the modern
well-regulated groceries where a refrigerator is a necessary part of
the equipment.
While the final chemical decomposition of spirit of nitrous ether
is complicated, the first step is the hydrolysis of the ethyl nitrite
with the formation of alcohol and nitrous acid, which may be re
presented by the following equation:
I'oIIsONO + HOH = C2H5OH + HONO.
Further decomposition rapidly results in the formation of various
products among them being ncetaldehyde, paraldehyde, acetic and
nitric acids, and ethyl acetate and -nitrate. The rapidity of the
hydrolysis is increased by light and heat, which again shows the
necessity of storing this preparation in a cool and dark place; but
while the present and past pharmacopoeias have specified dark
amber-colored vials as containers, perhaps not one pharmacist in a
hundred has followed these important directions. Since water is
necessary to effect hydrolysis, the ideal solvent for this preparation
would be absolute alcohol, which would reduce decomposition to a
PH.I RUA CE UTICAL REVIEW. 221)
minimum. But even with the use of the present official alcohol
(94. 1)'/! by volume) a preparation is obtained which will keep for a
reasonable length of time under proper conditions. However, when
water is added or dilute alcohol used for dissolving the ethyl nitrite,
decomposition goes on rapidly, even in the cold, so that the pre
paration becomes practically inert in a short time. There can be
absolutely no justification for this practice, nor for the sale by
manufacturers and jobbers of socalled F" and "4 F'' spirit of
nitrous ether which are prepared with dilute alcohol and soon be
come valueless.
Spirit of nitrous ether, once highly valued as a diuretic and dia
phoretic, has fallen into disfavor with the medical profession. The
compilation of analytical results fjiven at the beginning of this
article show conditions (probably no worse in Wisconsin than in any
other state) which alone would furnish sufficient grounds for this
disfavor. To this should be added the practice of physicians of pre
scribing this preparation with aqueous solutions, whereby it rapidly
weakens, and if the dilution is sufficient, may become almost inert
in a few hours. If properly prescribed and dispensed, spirit of nitrous
ether might regain the important place it once occupied in the
materia medica.
2:i0 PHARMACEUTICAL REVIEW.
Notes, mainly bibliographical, on two American Plants —

Sleepy Grass and Creosote Bush.*
By Albert C. Crawford.i
Very little is known concerning any poisonous or medicinal action

of the members of the Graminiae, at least in the fresh condition,
although after they have undergone fermentation some are believed
to be injurious to stock.2
A direct poisonous action has, however, been traced to a few
species, such as Panicularia aquation {Glycerin aquatics),3 certain
members of the genus Panicum, to various members of the genus
Sorghum* and also to the seeds of Paepalum scrohiculatum.
Some proof of a poisonous action has been brought against
Lolium temulentum, but according to Wilson5 Lolium free from
parasites is harmless and any possible injurious action Lolium may
have is believed due to them, a condition analogous to the ergot
infection of rye. A similar idea is held with reference to Phragmites
vulgaris (Arundo phragmites).
Avena sativa is said to contain an alkaloid, avenine, which
causes psychical excitement in horses—and Anthoxanthum odoratum,
owing to the coumarin which it contains, is likewise claimed to
cause some disturbance in animals, while suspicion has been raided
at times against Alopecurus geniculatus.
There are also some reports like those of Oserow0 in which
• Owing to a transference to other duties the writer will be unable to complete
these investigations, so only notes are published.
t Bureau ot Plant Industry, United States Department of Agriculture, Wnsh-
ington, D. C.
2 Vermast. Intox. von Plerden durch verdorbencs Gras. ThierartJs. vol. 20,
p. 188, 1881. A. Kecherches sur la Germination des Grafnes de Lin. Bull. Acad.
3 Jorlssen,
Koy. de Belgloue. H vol. 7, p. 737, 1884.
* Crawford, A. C. Poisonous action of Johnson Grass. Bur. Plant Industry,
U. S. Dept.. Agrlc. Bull. !)(). pt 4, 1906.
5 Wilson, A. S. On Lolium temulentum. Trims. Bot. Soc., Edinburgh, vol. II,
p. 457, 1873. Further Experiments with Darnel. Trans. Bot. Soc., Edinburgh,
vol. 12, p. 38, 1876.— Freeman. E. M. Seedfungus of Lulium temulentum. Proc.
Boy. Soc., Loudon, vol. 71. p. 27, 11103.
« Oserow. Ueber Krankh. d. Pferde, welche Aehnlichkeit mlt d. Cerebrospinal
Meningitis hnben. aber durch Verglftungen mit Grftsern von Stilatgriinden (Salz-
mooren) verursacht werden. AbHt. in Jahresb. hber d. Lelst. all! d. Geblete d.
Veterlnar Med., vol. 26, p. 226, 1906.
PHA RMACEITICA L REVIEW. 2:il
grasses grown on a particular soil are said to be poisonous. The

exact explanation of this is as yet lacking, but perhaps the injurious
action may be due to some inorganic constituent which is taken up
by the grass from the soil. Again, the. pollen of certain grasses is
said to bear some relationship to hay fever in man. Walsh," also,
has recently claimed that certain of the summer diarrheas of infants
are due to the injurious action of various grasses eaten by the
cattle which supply their milk.
Sleepy Grass. In New Mexico it is stated that if horses are
pastured in areas where a certain grass grows, the animals will be
come drowsy and sleep, from twenty-four hours to three or more days,
as if under the influence of a narcotic. This grass is found through
Colorado north to South Dakota and south to Mexico, and west
into southern California but reports of this action come mainly, if
not exclusively, from New Mexico and Mexico. There is, however,
some doubt, in the writer's mind as to whether this so-called nar
cotic action may not be a dullness due to the gastro-intestinal irri
tation of a poison, perhaps a volatile one, rather than to the action
of a true narcotic.
Gillespiet* describes the animals after eating the grass as present
ing rather a pitiful appearance. The horse stands with its head and
tail drooping, its body quivers and sweat rolls off its sides. The
respiration becomes more rapid, tlie heart action and urinary
secretion are said to be increased. Diarrhoea is also reported.
Moreover, there are symptoms of irritation and strangury. Cattle
are but rarely affected and seem to avoid the grass, while sheep are
believed to be unaffected by it. It is usually agreed that horses
after one such pasturing will not eat the grass again, and that
native animals may be pastured in such areas with impunity. As
yet we know of no actual death in this country from eating this
grass, but one ranchman has reported that horses after eating it
will die the following winter, that is, the period in which only the
strotig survive.
This so-called narcotic action is claimed to be especially marked
in spring and to reside in the radical leaves," but Bailey,10 who tra-
1 Walsh, J. L. An Uurecognized Ktlological Factor in the Summer Diarrheas
of InfantB. Med. Kec., vol. 70, p. 41<>. 11*0(5.
* Gillespie, A. Preliminary Note on the Pharmacological Action of Stipn viri-
tlula. Brit. Med. Jour., 181*8," vol. '2, p. lo.19.
9 Havard, V. The Sleepy Grass. Garden and Forest. Vol. 4. 1891, p. 111.
Llewellyn. J. F. Some Varcotic Plant.*. Proc. Missouri Phurm. Assoc.. 1901, p. 6'2.
10 Ballev, V. Sleepv Grass and Its Effect on Horses. Science ti. s., vol. 17,
. p. 892, 1908.
232 Pll. I llllA CE UT1CA 1, KE VIEW.
veled during September on t he Sucramento mountains, noted ilmt

even then his horses were affected from eating this grass. Bailey
shelled a handful of the seeds of this grass and ate them without
any injurious action upon himself. The grass having this action
has been identified by him as Stipa vnscvi. Gillespie claimed that
the sleepy grass was Stipa viridula and from certain experiments on
frogs and rabbits concluded that besides a narcotic action it also
exerted a sudorific and diuretic effect, that it caused a more
rapid action of the heart and respiration and that it acted as an
irritant, but these experiments are entirely insufficient to yield any
conclusions as to the pharmacological action of the grass.
rainier11 also identified this plant as Stipa viridula, but all three
authors evidently refer to Stipa vaseyi, as this subdivision in species
was not made until 1H98.12 Previous to this Stipa vatejri was
designated as Stipa viridula robusta. It is claimed that true ,S'f//),.<
viridula is a good pasture grass, and is devoid of injurious action.
Narcotic action is also claimed to be produced by Stipa inebrious
(.Mongolia) and Stipa Siberian (India). In Kashmir horses become
incapable of movement and die after eating a Stipa, presumably
Stipa parviffora. Cows are said not to eat this grass. The natives
there find that the administration of vinegar or unripe apricots is
effective ill saving such cases of poisoning.13 In China eating of
Stipa inebrians is believed to cause cattle to lose their hoofs.14 This
action might, however, be realty due to an ergot infection of the
grass as the loss of the iioof would occur under such conditions.
In South Africa a similar narcotic action has been attributed to
a grass growing there and transport drivers refuse to let their teams
stop in areas where this grass grows, as the cattle become affected
and show "intoxication to an alarming extent."1"'
Some other species of Stipa, as S. capillata, S. ppartea and S.
neesenna, etc., may kill stock by injuring mechanically the intestinal
walls or by wounding the skin and thus leading to fatal infec
tions.i0 (Actinomycosis.)
tt Va«ev, G. Special UBpB and Properties of some Mexican Grasses. Bull.
Torrey Hot. Club. vol. 14. 1887. p. 1)9.
t2 Lamson.Kcrlbner, F. Studie* on American GrnsHes. Dlv. of AgroHtologv,
U. S. Dept. Airrlc., Bull. 11, lsits, p. 46.
I3 llance, II. F. Supplementary Note on Intoxicating Grasses. Journ. ot Bot.
n. s., voi. 6, p. 207. I*7i.
i* Goexe, E. Glltige Grilser. Wlen Illus. Gart. Zelt., vol. '21. p. ii!!4, 1902.
is Amor. Journ. of Scl. [3] 8, p. till. (1874).
™ Blancbard. Verletzuugcn durch eine umerikaniHche Graminee: Stipa neeslana,
Oer Thierarzt. vol. 45, p. <>, 1it0H: Accidents causes par lme Graminee A mdricnlue,
An-h. de Parasltol, vol. 10, p 187. 1903. — Greshoff. M. Beschrijvlng d. gift. in
bedivelm. pianten., 11)00, )>. 100. — Marschall von Biebersteln, K. A. Flora Taurlco-
Caucaslea, vol. 1. p. 7<!, 1808.
PHAKMACEUTICAL REVIEW. 233
Some species of Spitn found on thp high plateaus of the Argentine

Republic and Bolivia are claimed to be very poisonous to horses
and mules. These animals die in a few hours after eating these
grasses. Native herds are said not to eat these plants but imported
animals readily do so. These grasses were proved to be Stipn
leptostHchyu and .V. hystficina. Heim and Hebert17 obtained from
these species a f^lucoside which split, up and yielded hydrocyanic
acid. (0.02 per cent, of dry grass.)
Hackel1* says that it is not improbable that various other
Slipas in North America and Asia will be found to yield hydrocyanic
acid. A chemical and pharmacological study of Stipn vnspyi so far
as the writer can find1" has never been made. It is to be suspected,
however, that hydrocyanic acid will be found in the fresh poison
ous plants. One old dried specimen of this plant collected in
Mexico several years ago, however, failed to show hydrocyanic acid
by the writer's tests. A similar negative result was obtained on
testing a mixed specimen of >Vtf/M viriilnhi, S. pringlii and some Poa
which was shipped in chloroform water from near (Mouderoft, New
Mexico. The aqueous extract of this mixture of grasses failed to
produce any narcotic action when fed to rabbits. Can it not be
that the principle causing this injurious action to horses is simply
the product of a morbid metabolism of the plant or may only occur
at a certain period in the normal metabolism of the plant'.'
It has been suggested that, perhaps this grass may yield a
principle useful in genito-urinary medicine.
Creosote Bush. One of the plants common to the arid
region-0 of our Southwest,, but, especially common to Arizona and
the t'oloiado Desert, is known popularly as creosote bush or
scientifically as Cuvillea tridentata (Lurreu mexiaina). Coville has
reported that the dead branches of this plant will remain for
years without decomposing. This plant shows a peculiar adapta
tion*1 to the arid conditions in that it has a resinous covering
t7 Hehert, A. Kecherches stir la presence de l'ncide cyanhydrl(|tie chez dlverses
plantes. Bull. Sue. Calm, de Paris, s., vol. H.j. 190(5, p. 919.
is Hackel, K. I'eber irtftigc Urnser. Mitt. d. Naturw. Vereines f. Ktelermark.
1904, p. LV1I, 19n!i.
i» Kep. of Work nf Auric. Exper. Sta. Univ. Calif., 1903. p. 1as.
30 Merrlam, C. H. Notes on the dlstrib. ,'f Trees and Shrubs in the Deserts
and Desert Kunês of southern California. Dead Valley Expcd. North American
Fauna, No. 7, U. S. Dept. Agr.. p. 294, 1S93. — Coville, F. V. Botany of the Dead
Valley Expedition. ContHb. from V. s. Nat. Herbar., vol. 4,'pp 44. 7*, i H9a. —
Dewev. \'. H. Characteristic Vegetation of the Desert KeIzlon from Western Te.vas
to Central Arizona. Rep. Sec. Agrlo, for 1891, p. H.1H, 1S92.
3I Frlngle. C. O. 1.orest Vegetation of North Mexico Garden and Forest,
vol. 1, p. 524, 1SHS.
which by minimizing transpiration protects it against the drought.

This resin is said to he more abundant in dry than in the rainy
season. 22
The name creosote bush was received on account of the peculiar
odor which it gives off. This odor has been described by some as
offensive, others describe it as more or less' pleasant.2s Cattle will
not eat the plant probably on account of this odor.24 Among cer
tain of the ranchmen of Arizona it is the belief that creosote bush
is one of the causes of abortion in sheep. A quantity of this was
collected for examination in southern Arizona. These leaves were
dried at room temperature and after grinding, 740 grams were
extracted with 41 per cent alcohol. After extraction t he liquid was
evaporated in vacuo at about 40° C., and the fluid made up to
1500 cc. with 31 per cent alcohol, so that 2 c. c. of the fluid corre
spond to about one gram of the dried leaves. On January 3. 1905,
10 cc., which corresponded to 5 grams, were injected subcutaneously
into a rabbit weighing 2320 grams. This produced absolutely no
symptoms. On January 5th, a pregnant sheep was injected sub
cutaneously with 10 cc. of this liquid without the production of any
symptoms. On January 30th, 17 cc., corresponding to 8.5 grams,
were injected subcutaneously into the same sheep; no symptoms
were produced.
On January 30th, 20 grams of the dried plant were placed in
gelatine capsules and gently pushed down the sheep's throat. This
also produced no symptoms. On February 1st, 40 grams were
given without producing symptoms. Thirty-two days later the
sheep bore a perfectly healthy normal lamb at normal period, so
that evidently the belief in the abortifacient properties of the creo
sote bush is unfounded.
The reddish-brown lac which occurs on this plant and which is
deposited by a scale insect, Caneria lurreae, is used by certain
Indians for cementing the arrow heads to the shaft.25 The Zunis
use it in their lacquer work, for coating baskets, inlaid work, etc.,28
22 Spalding. V. M. The Creosote BuHh (Covillea trbleutnta) in its Relation to
Water Supply. Bot. Ua»., vol. 38, p. 122, 1904. — MavDougnl. D. T. Some A»pects
of Desert Vegetation. Contrlb. from New York Bot. Garden. No. 46. 19o:i, p. 254.
29 JameH, G. W. WonderH of the Colorado Desert. vol. 1. p. 220. I90H.
2* Emory, W. H. Notes of a Military Reconnaissance from Ft. Leavenworth,
in Missouri, to San Diego, Cat, 1848, p. 1.18.
25 Covllle, F. V. Pannminr Indians of California, Amer. Anthropologist, vol. 5,
p. 861. 181)2. — Palmer. E. Plants tised by the Indians of the United States.
Amer. Naturalist, vol. 12, 1878, p. <>54. — Volkens. o. Ober Ptlanxen mlt lacklrten
Bliittern. Ber. dentsch. hot. Oesells., vol. 8. p. 120, 18it0.
2« disking. F. II. Primitive Copper Working. Amer. Anthropologist, vol. 7,
p. !>8, 1894.
PllARMA CELTICAL REVIEW. 235
while the Pimas manufacture a cement from it which they use in

mending pots.2" These Indians likewise make balls of the resin
which are used in their sports. 28 It is claimed a0 that the plant has
marked antiseptic and stimulant properties and Lowe suggests that
"an excellent ointment" might be made »ith it.
It is also used in connection with hot baths in the treatment of
rheumatism 3,t but it is a question whether in reality the 'hot baths
are not the curative agent rather than the creosote bush.
The Coahuilla Indians also use the plant in the treatment of
certain forms of bronchitisa1 and the Apaches use the gum as a
styptic. Sonora gum or Arizona shellac, which is the deposit from
the scale insect on this plant82 and also on the Acucoia gregffii, is
shown by iStillmann33 to have probably the same chemical compo
sition as the Indian shellac, so that according to some there is no
reason why America should not thus have her own independent
shellac supply.34 This gum is believed to be used by the brewers in
California in the manufacture of porter.
This reddish-brown lac on the branches, according to Loew
yields a red coloring matter which gives the reactions of cochineal.
The lac is said to be used by Mexican shoemakers to dye leather
red.a5
The writer found that the characteristic odorous principle of the
plant could be distilled over by steam and could be partly if not
entirely shaken out from this distillate by benzol. The benzol
shaking in one experiment yielded crystals.
« HrdllCka, A. Notes on the Pima o( Arltona. Amer. Anthropologist n. s.,

vol. 8, pp. 44—45, 1906.
»» Durand, E.. and Hllgard, T. C. Botan. Ueport. Explor. and Surveys lor a
Railroad Route from the Miss, river to the Paoitle ocean. Vol. .". pt. 3, 1855, p. 6.
2s Lowe, C. B. harrea mexieana, Amer. Journ. of Pharm.. vol. 70. 1S9S,
p. 2a7. — Kami, R E. Desert flora of Phoenix, Arizona. Bull. Torrev Bot. Club,
vol. so!!0.Vasey.
1908, G.,
p. and
805. Rose, J. N. List of Plants collected by Dr. Edward Palmer
in lower California and western Mexico in 1890. ( ontrlb. from U. S. Nat. Herb.
Vol. 1. I". S. Dept. Agrlc. Dlv. of Botany, 1890—95, p. 68.— Wheeler, G M. Rep.
upon t'nlted States Geograph. Surveys west of 100 meridian. Botanv. Vol. ti,
p. 41, 1878.
" Barrows, D. P. Ethno-Botany of the Conhullla Indians of southern Cali
fornia. 19i 0, p. 48.
3> Wilson. J. H. Leaves anil Stipules of Larrea mexlrnnu. Proc. Bot. Soc..
Edinburgh. Vol. 19, p. 1K5, 1898.
»' Stillmunn, J. M. Gummllnck aus Arizona und (ulifornlen. Ber. d. deutsch.
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'* Spon's Encyc. of Indust. Arts, Manuf. and Raw Commercial Products, Lon
don. 1882. vol. 2, p. 1673.
s5 Havard, V. Rep. on Flora of West. and South. Texas. Proc. C. S. Nat.
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• Ledger, — General paper on Inc. See Watt, G. Luc and the Lac
No. 9.
2«(i PMA RilA CE VTIVA L REVIEW.
Literature on Medicinal Plants and Drug Plant Culture*
By Albert Schneider.
(299) H. H. Rlsby. South American Drugs. Prop. X. Y. State Pharm.

Assoc.. 158—170. 1888.
(SCO) II. II. Ki'sby aad Vai.arv Harvard. Study of the American Medi
cinal Flora. Am. Journ. I 'harm. 09, pp. 423—120. 18!tT.
t ;X)1 ) W. Sainders. Somc Medicinal Plants of Canadian Growth. Proc.
A. Ph. A. 18, pp. 182—187. 1870.
IW'2) W. Sainders. On the Manufacture of Rubber from Milkweed.
Pro:•. A. Ph. A. 23, pp. 0.15—(EiN. 18T."i.
I'.'XK') W. Sainders. On the Germination of Seeds of Medicinal Plants.
Proc. A. Ph. A. 30, pp. 505—508. 1882.
CX'4) J. C. Saweb. Odoragraphia : A Natural History of Paw Materials
. and Drugs used in the Perfume Industry, Including the Aromatics
used in Flavoring. London. 1893.
(2(5) J. C. Saweb. Khodologia : A Discourse on Poses and the odor of
Bose. Brighton.
i :,(!(!i L. E. Sayre. Organic Materia Medica and Pharmacognosy. Phila
delphia. 18!)!!.
I SOT) L. F. Sayre. Loco-Weed. Proc. A. Ph. 38. pp. 107—108. 1890.
1 808) E. Scnaer. Japanese Drugs. (Abstract.) Proc. A. Ph. A. 2,1,
p. 120. 1875.
(309) Karl Sciiebzeb. The Cinchona Forests of South America. Am.
Journ. Pharm. 35, pp. 124—128. 1803.
(310) J. O. Schlotterbeok. Botanical Garden and Arboretum of the
University of Michigan. Proc. A. Pll. A. 47, pp. 491—192. (abstr.)
181)! ).
(311) Albert Schneider. Suggestions on the Cultivation of Medicinal
Plants in California. Pacific Druggist, April and May, 190.1.
(312) Albert Schneider. Gardens■ of Medicinal Plants. Am. Journ.
Pharm. 7(1, pp. 1!)—30. l!MU.
(813) A. Schneider. The Cultivation of Cinchonas on the Pacific Coast.
Druggists Circular. 40. pp. 420—430. (December) 1905. Gives
the references to the literature on the History of Cinchona Cul
ture in India and Java.
1 314 1 A. Schneider. Notes on the Sources of Rubber. Pacific Druggist.
March, 1905.
(315) A. Schneider. The Medicinal Plants of the California Indians.
Mercks' Report. 1900.
(310) SciioMiuRUH. Perfume Plants of South Australia. Pharm. Journ.
Trans.. Sept. 1879.
• Continued from |>aê 'J 14.
1 317) W. Schwabe. On B-cinchonla, n new alkaloid from cbinoldino.

Am. Joum. Pharm. 33, pp. 417—121. 1801.
(318) W. A. Setciieli, and N. U Gardner. Algae of Northwestern
America. Berkeley Univ. Press. 1903.
(319) G. Sharp. True and False Cactus grandlflorus. Am. Journ. Pharm.
70, pp. 154—157. 1898.
(320) Thomas Shaw. The ltape Plant: Its History. Culture and Uses.
Dept. Agriculture, Farmer s Bulletin No. 11. 1895.
(321) Geo. W. Shaw. The California Sugar Industry. Univ. Calif.
Publications. College of Agriculture. Bull. No. 149. 1!H>:(.
(322) C. C. Sherbard. Saw Palmetto (Sabal serrutata). Proc. A. Ph. A.
42. pp. 309—315. 18!>4.
(323) C. H. Shinn. Culture Work at the Substations. Univ. Calif. Pub
lications. College of Agriculture Bui. No. 147. 1899—1901.
(324) A. S. Sholl. Zypadenus fremontii. Proc. Calif. Pharm. Soc. 188i.
(Abstract.)
(325) P. S. Simmonds. Leaves— Medicinal Uses. Am. Journ. Pharm. 02.
pp. 193—197. 18!Ht.
(320) W. Simpson. The Names of Medicinal Plants of Commercial
Value that are Gathered in North Carolina: Their Value and
Relative Amount Sold in this Country and Exported. (Am. Journ.
Pharm. 0(!, pp. 480—490. 1894.) Proc. A. Ph. A. 42, pp. 210—
220. 18!>4.
(327) J. K. Small. A Monograph of the North American Species of the
Genus Polygonum, .Mem. Dept. Bot. Colum. Univ. 1895.
(328) C. B. Smith and C. F. Lonoworthy. Chestnuts. U. S. Dept. Agr.
Farmer's Bulletin No. 114 (pp. 9—14). 1900.
(329) E. R. Squibb. Pharmacy of the Cinchonas. Am. Journ. Pharm. 39,
pp. 289—303, 398—114, 513—529. 1807. A very complete dis
cussion of the pharmaceutical preparations made from Cmchona
Bark.
(330) B. F. Stacey. Medicinal Agents of Indians. Proc. A. Ph. A. 21,
pp. 610—621. 1873.
(331) F. Stearns. The Peppermint Plantations of Michigan. Am. Journ.
Pharm. 31, pp. 33—12. 1859.
(332) F. Stearns. The Medicinal Plants of Michigan. Proc. A. Ph. A.
1858. (Am. Journ. Pharm. 31. pp. 28—32. 18."!).)
(333) J. G. Steele. The Pines of California. Proc. A. Ph. A. 37, pp.
226—244. 1889.
(334] J. G. Steele. Griutlvlia robuxtu. Proc A. Ph. A. 23, pp. 037—543.
1875.
(335) J. G. Steele. Notes on the Oaks of California. Proc. Calif. Pharm.
Soc. 1887. (Abstract.) . •
(330) James G. Steele. Kei»rt of the Drug Market of San Francisco
(Medicinal Plants of California). Proc. A. Ph. A. J7. pp. 508—
014. 1879.
(337) Stephen Powers. Aboriginal Botany. Proc. Calif. Acad. Sc. 5.
(338) Geo. W. Stoeckel. Indigenous Materia Medica. (Pennsylvania.)
Proc. Penn. Pharm. Assoc.. pp. 140- -148. 1886.
(339) L. Tumor. The Febrifuge Principle in the Bark of OUu Eiuopca.
Proc. A. Ph. A. (nhstr.) 25. p. 138. 1S77.
(340) J. B. Thomas (T. H. P. De Tavera). The Medicinal Plants of the

Philippines. Philadelphia, 1901.
(341) M. Timbal-Lagrave. On the Influence of Cultivation upon Medi
cinal Plants. Am. Journ. Pharm. 34, pp. 208—273. 1802.
(342) A. M. Todd. Mint: Its Early History and Modern Commercial
Development. Proa A. Ph. A. 51, pp. 271—279. 1903.
(343) Torrey and Gray. Botanical Reports of the P. K. R. Explorations.
War Dept., Vol. II.
(344) S. M. Tracy. Cassava. U. S. Dept. Apr. Farmer's Bulletin No.
167. 1903.
(345) H. Trimble. Some Indian Food Plants. Am. Journ. Pharm. 60,
p. 593. 1889. 02, pp. 281, 598. 1890.
(340) H. Trimble and J. C. Peacock. Canaigre Tannin. Am. Journ.
Pharm. 05, pp. 101—109. 1893.
(347) II. Tbimble. The Cultivation of Ginseng. Am. Journ. Pharm. 00,
pp. 399, 401. 1894.
(348) II. Trimble. California Soap riunt. Am. Journ. Pharm. 02, pp.
281, 598. I 89U.
(349) C. M. Troppman. Rhododendron occidentalc. Proc. Calif. Pharm.
(350) C. M. Trofpman. Chinese Pharmacy. Proc Calif. Pharm. Soc.
1887. (Abstract.)
(351) A. C. True. The Date Palm in the United States. U. S. Dept. Agr.
Farmer's Bulletin No. 92. 1899 (pp. 10—19).
(352) A. C. Trie. Tropical and Subtropical Fruits. U. S. Dept. Agr.
Farmer's Bui. No. 109 (p. 21). 1903.
(353) R. H. True. Cultivation of Medicinal Plants. Am. Joum. Pharm.
74. pj). 41!)—122. 1902.
1^354) Rodney H. True. Cultivation of Medicinal Plants. (Paper read
before the Philadelphia College of Pharmacy, Nov. 17, 1903). Am.
Journ. Pharmacy 75, pp. 584—580. 1903.
(355) J. W. Tryon. Mimulus ylutinosis (Flowering tops). Proc. Calif.
(350) Univ. Calif., Coll Agr. Bui. No. 158. 1904.
Gives full information regarding the manufacture of Olive
Oil. Illustration of apparatus, etc.
(357) University of Cai.fiornia, College of Agriculture. Reports 1887.
(Treats of Cinchona culture efforts.)
(358) Univ. Calif., Coll. Agr. Bui. Nofl 149. 1903. The History, Com
merce ,and Manufacture of Sugar in California.
(359) Univ. Calif., Coll. Agr. Bui. No. 150. 1904. Gives information
regarding the occurrence, use, etc. of oaks (Quercus Douglasii,
Q. durnosa, Q. dumosa bullata, Q. Wislizcui, Q. chrysolepsis, Q.
Californica, Q. garryana) and the Poison Oak [Rhus diversiloba).
(360) Univ. Calif., Coll. Agr. Report for 1894—1905. Contains infor
mation on soil, drainage, plant diseases, olives, culture of al
monds, peaches, plums, apricots, figs, pears, nectarines, garden
vegetables, camphor trees, oaks, mulberries, walnuts, carob. eu
calyptus, date palm, sassafras, canaigre, etc.
(361) U. S. Dept. Agb. Bureau of riant Industry. Bui. No. 4!). 1903.
Full Report on the culture of the Central American rubber tree.
(362) U. S. Dept. Agr. Bureau of Plant Industry. Bui. No. 51. 1904.
Treats of golden seal ; collection, occurrence, use, cultivation, etc.
(363) U. S. Dept. Agr. Farmer's Bulletin No. 25. 1896. The Culture
and Uses of Peanuts.
(364) U. S. Dept. Agr. Farmer's Bulletin No. 27. 1895. The culture of
flax for its seed and liber.
(365) U. S. Dept. Aob. Farmer's Bulletin No. 39. 1890. Contains full
information on onion culture.
(360) U. S. Dept. Aob. Farmer's Bulletin No. 45. 1897. Contains use
ful suggestions on the extermination of pests which infest stored
Brains. This will be found useful in treating similar pests which
infest vegetable drugs.
(307) U. S. Dept. Agr. Farmer's Bulletin No. 50. 1899. Full informa
tion on sorghum culture and its value as a forage plant.
,308) U. S. Dept. Ac.b. Farmer's Bulletin No. 52. 1901. The sugar beet:
culture, seed development, manufacture and statistics. IIlustr.
tion regarding mushroom culture.
tion with regard to asparagus culture, insect enemies, fungus
diseases, etc.
(371) U. S. Dept. Agr. Farmers' Bulletin No. 62. 1903. Contains sug
gestions on marketing farm produce, including fruits and
vegetables.
(372) U. S. Dept. Agr. Farmer's Bulletin No. 09. 1898. Suggestions on
flax culture, heating green-houses, and on the use of fertilizers.
(373) U. S. Dept. Agr. Farmer's Bulletin No. 73. 1898. Contains sug
gestions on loss of soil fertility, availability of fertilizers, on seed
selection. Also on the culture and use of Jerusalem artichoke
(Helianthus tubcrosus).
(374) U. S. Dept. Agb. Farmer's Bulletin No. 89. 1904. Full informa
tion regarding the cowpea (Yigna sinensis). Useful forage plants
and crop rotation.
(375) U. S. Dept. Agr. Farmer's Bulletin No. 94. Useful suggestions on
gardening, selection of ground, tilling, selection of seeds, seeding,
transplanting, etc. Contains specific directions with regard to the
culture of the Jerusalem artichoke, asparagus, beans, beets, cab
bage, carrots, cauliflower, celery, lettuce, martynla, okra, onions,
parsley, parsnips, peas, potatoes, radishes, rhubarb, salsify,
spinach, squash, sweet corn, sweet potatoes, tomato, and turnips.
Of great general value.
(376) U. S. Dept. Agb. Farmer's Bulletin No. 110. 1900. Full informa
tion on rice culture in the United States.
tion on the culture, etc. of the sweet potato.
(378) U. S. Dept. Agr. Farmer's Bulletin No. 133. 1901. Contains use
ful suggestions on fertilizing: on the culture of celery and on the
fumigation of trees.
240 PHA KMACE UTICAL KE VIEW.
tion regarding the cultivation of the pineapple; on canning, ship
ping, on crop diseases, etc.
tion with regard to celery culture, celery diseases, methods of
bleaching, etc.
1381) U. S. Dept. Agr. Farmers Bulletin No. 149. 1902. Contains sug
gestions on gardening, culture of plums, onions, muskmelons, and
strawberries.
1382) U. S. Dept. Agr. Farmer's Bulletin No. 153. 1902. Treats of the
plant parasites of the Pacific Coast and the methods employed to
combat them; the value and use of various germicides.
(383) U. S. Dept. Agr. Farmers' Bulletin No. 154. 1902. Contains sug
gestions on establishing fin it gardens, combined fruit and
vegetable gardeas, etc., number of plants per acre. etc.
(384) U. S. Dept. Agr. Farmer's Bulletin No. 157. 1902. Contains use
ful suggestions on the propagation of plants from cuttings, bulbs,
tubers, rhizomes ; by layering, grafting, etc.
(385) F. S. Dept. Agr. Farmer's Bulletin No. 158. 1902. Suggestions on
building small Irrigation ditches. Useful for Californians.
<38«) IT. S. Dept. Agr. Farmer's Bulletin No. liil. 1902. The entire
Bulletin devoted to practical suggestions for fruit-growers, as
tilling, pruning, fertilizing, spraying, etc. Illustrations of spray
ing outfits.
(387) U. S. Dept. Agb. Farmer's Bulletin No. 1<>4. 1903. Bape culture,
with special reference to Oregon conditions.
tion regarding cassava (3lanihot aipi and varieties) culture. This
report should be supplemented by consulting the Reports of the
University of California. Dept. Agr., and those of the California
1 lorticultural Society.
(389) U. S. Dept. Agr. Farmer's Bulletin No. 174. 1903. Full report on
broom corn culture in the United States.
(390) U. S. Dept. Ai;b. Farmer's Bulletin No. 180. 1 ! MM. Contains sug
gestions on the culture of taraxacum, on sterilizing green house
soil, and on macaroni wheat.
(391) U. S. Dept. Ann. Farmer's Bulletin No. 187. 1!M>4. Suggestions
on soil drainage.
(392) U. S. Dept. Agr. Farmer's Bulletin No. 188. 1904. Contains a Jist
of tweuty-flve common weeds which have medicinal pro1>erties,
with suggestions on cellecting. drying and marketing them.
(393) U. S. Dept. Agr. Farmer's Bulletin No. 195. Much useful informa
tion on establishing larger and smaller gardens, hot-hods, cold
frames, pits. etc. Gives specific instructions (with illustrations)
on the culture of ageratum, alyssum, aster, balsam, calendula,
California |>oppy, coreopsis, campanula, candy-tuft, castor beau,
chrysanthemums, clarkia. cockscomb. Cobaea scandens. colum
bine, cane !lower, cornflower, cosmos, evening primrose, forget-me-
not, four-o'clock, foxglove, gaillardia, hollyhock, iimmea. moon
flower, cypress vine, larkspur, lobelia, marigold, nasturtiums.
nemophila, pansy (viola tricolor), petunias, phlox, pinks, poppy,

1K)rtulacca, scarlet sago, snapdragon, stocks, sunflower, sweet
peas, verbenas, and zinnia.
(394) U. S. Dept. Aui:. Farmer's Bulletin No. 198. 1904. Full informa
tion with regard to culture, packing, shipping etc. of strawberries.
(395) Chas. H. La Wall. The Drug nnd Herb Vendors of the Sidewalks
of Philadelphia. Am. Journ. Pharm. 72, pp. 59—00. 1900.
(390) O. A. Wall. Notes on Pharmacognosy. St. Louis, 1902.
(39V) Theo. II. WAboi.EWObni. Pharmaceutical and Economic Plants of
Jamaica. Trans Brit. Pharm. Conf. 421—427.
(398) YV. Weaver. Cinchona Cultivation in California. Proc. A. Pll. A.
(abstr.) 29, pp. 151—152. 1880.
( :>ii!)) B. K. Weaver. The Olive and its Product. San Francisco and
Pacific Druggist, 10, pp. 17—22. 1904.
(400) II. J. Webber and E. A. Bessey. Progress of Plant Breeding in
the United States. Yearbook Dept. of Agriculture, pp. 405—190.
1899.
(4(>1) J. H. Weuber. Influence of Environment in tlu' Origination of
I'l.int Varieties. Yearlwok Dept. of Agriculture, pp. 89— KMi. 1890.
<4<;2) II. S. Wellcome. Verba xuutu of California. Proc. A. Ph. A.
(abstr.) 24. pp. 134—135. I870.
(40.'!) W. T. Wen/.ei.l. On Abietinc. Sau Francisco and Pacific Druggist,
10. pp. 13—14. 1904.
(104) W. T. Wenzei.i.. On Oleum ChnuiaecyparUs Lawsonie. Proc. Calif.
Pharm. Soc. 1S884. (Abstract.)
(405) W. T. Wenzei.i.. Pharmacy in California. Proc. A. Ph. A. 18, pp.
198—201. 1870.
i 100) Carl YVeschke. The Medicinal Plants of Minnesota. Pharm.
Kundschau. July, 1890.
(407) II. M. Wheeler. L'. S. Geog. Survey, West of the 100th Meridian.
0. (Botany.)
t 408) M. Whitney and M. L. Floyd. Growth of the Tobacco Industry.
Yearbook of the Dept. of Agriculture, pp. 429—140. 1899.
<409) YV. B. YVhitney. Euphorbia cremocarpus. Proc. Calif. Pharm.
(410) M. Whitney. Methods of Curing Tobacco. U. S. Dept. Agr.
Farmers' Bulletin No. 00. 1898.
(411) E. J. Wickson. Irrigation in Fruit Growing. U. S. Dept. Agr.
(412) J. YViesner. Kohstoffe des Ptlanzenreicbes. 2 vols^ Leipzig, 1900—
1903. Vol. I is most useful.
t 413) II. W. YViley. Soil Ferments Important in Agriculture. Y"earbook
Dept. Agr., pp. 09—102. 1895.
1414) Wii.kes. U. S. Exploring Expedition. 4, p. 302. 1845.
(415) A. P. Woods. The Relation of Nutrition to the Health of Plants.
Yearbook of Agriculture, pp. 155—170. 1901.
(410) YV. M. YorNG. Mrfiarrhiza California/. Proc. Calif. Pharm. Soc.
1882. (Abstract.)
(417) Zoe. 1—4, (1890- 1N94.>
242 PHARMA CE {. TICA L RE VIE W.
SUBJECT INDEX TO LITERATURE.
(The numbers refer to the serial numbering of the author citations.)
Abletlnc : 403 Calif, pines 333

Aconite 312 Calif, plants 77. 262—265
Agave Americana. .. .170, 175, 251, 252 Caltf. poisonous plants 18
Agaves 232, 254 Calif, survey 38
Agaves, culture 207 Calif, wild flowers 267
Ailanthus glandulosa 201 Camphor 292
Algae, marine 1, 1<18 Camphor, Ngal 13o
Algarohla glandulosa 52 Canadian med. plants 301
Alkaloids, vegetable 178 . Canutlllo 55
Almonds 250 Cape St. Lucas flora 24
Aloe. American 170, 175 Carlo papaya 177, 189, 296
Mpinia ofticlnarum 20 Cascara sagrada 297
Ustonla constrlcta 224 Cassava 344, 388
\merlcan agave 251, 252 Castanea leaves 53
American drugs 220 Celery culture 14, 378 380
American ginseng 253 Century plants 232
American med. plants 241 Cephalanthus occidentals 142
Ameilcan opium 122 Cereus 01
Amygdaiis 250 Cheap drugs 19 t
Ananas 291 Chenopodium Calif 25»
Anemopsls Californlca 211 Cherokee med. plants 9i
Annatto 126 Cherry harks 11, 12
Aplum gravcolens 8 Chla . 260
Apple, balsam 182 Chinese pharmacy 233, 350
Areca catechu 172 Cinchona ■ ■ • 309
Areca nuts 2 Cinchona alkaloids 15, 31 t
Argentine med. plants 238 Cinchona barks 150
Asparagus culture 137, 370 Cinchona bark assay 15
Asplenlum Felix foemlna 30 Cinchona bark, false 39
Assay of Cinchonas 15 Cinchona cultivation
Astragali, poisonous 119 41, 79, 80, 138, 229, 230, 231
Attar of rose 294, 305 Cinchona cult, in Calif... 258, 313, 398'
Australian fever bark 244 cinchona, Jamaican 283
Australian plants 218 Cinchona preparations 329
Citrus culture 204
Italsam apple 182 Climate 169
Bark, Cinchona 39 Clover, red 2<5
Bay laurel 145 Coahullla Indians 10
Beet, sugar 308 Colorado flora 277
Belladonna 312 Colorado weeds 70
Benne culture 266 Coniferae 13
Benzoin 120 Convallaria majalls 130
Berberls aqulfollum 0 Cottonwood 23
Birch oil 184 Cow pea "74
Blxa orcllana •••• -Ij" Creating new fruits lis
Bot. gardens 310, 311 Cree Indians 107. lj>9
Bouldln Island 30 Crocus satlvns 146. 208
Brassica rapa Croton procumliens »4
Brazilian drugs 163 Cultivation of Cinchonas
Brazilian plants 41. 79, 80. 138, 313
Broom corn 141, 3*9 Cultivation, med. plants... 73. 75. 158.
Buckthorns 297 161. 162, 313. 353, 354
Buckthorn, structure of li(1 Culture of jalap 92
Buhach 24" Cusso • • • 109
Bulgarian roses 294 Cyprlpedlum poison *>, .«!
.Bulletins. Calif 44
Bulletin, farmers 4. Dammara australls 247
Burdock . . 2iJV Dnmar Gum 247
"Bums" vegetation —> Date palm 351
Death Valley 65
Cactus grandlflorus 319 Deer's tongue 239
California Bay laurel 154 Desert laboratory 63
Calif, cinchona culture 198 Dletarv. vegetable 66
Calif, flora 38, 137 Dlgitailn 186
Calif, herb lore 22 Digitalis 312
Calif. Islands flora 2« Drainage 360
Calif. Manna .......212 Drainage of soil V"2:l
Calif, med. plants 9, 118. .i12 Drugs 72, 83. 306. 396
Calif, oaks 335 Drugs. American 220 to 229
Calif, opium Z2« Drugs. Brazilian 103
Calif, pharmacy 40o Drugs, cheap 197
PHARMACEUTICAL REVIEW. 24H
Drug culture 147, 187, 190, 196, Herbs, English 147
198, 312, 341, 353, 354 Herb lore 22
Drug export 132 Herb vendors 395
Drug history 112 Heteromelas arbutifolla 214
Drugs, Japanese 164, 165, 308 History of drugs 112
Drugs and medicines 87, 241 History of horticulture 156
Drug pests 366 lloarhound 290
Drug plants 87, 192, 222, 223, 241 Home plants 77
Drugs of San Francisco 336 Honey, poisonous 179
Drug vendors 200, 395 Hop culture 284
Hops 104. 108
Echinacea angustifolia 210 Hopl Indians 101, 166
Eihlnov-actus 62 Humulus lupulus 104, 108
Economic plants 134, 153, 154 Hydrastis 362
Edible kelps 168 Hypogaea 136, 363
English, drugs 147
Kschscholtzla 37 Indian food plants 143, 345
Eschscholtzla alkaloids 103 Indian medicinal plants. .. 50, 98, 159,
Essential oils 110 259, 261, 315, 330, 337
Euphorbia eremocarpus 409 Indians 66, 278
Euphorbia ocellata 202 Indians, Conhuilla 10
Experimental plant culture 121 Indians, Hopl 160
Export of drugs 132 Indians. Panamlnt 64
Indians. Swampy Cree 107
Ealsp Cinchona hark 39 Indigenous plants 91
Fanner s bulletins 42 Insect flowers 246
Ferments. in soil 413 Insect powder 246
Ferns 268 Irrigation 169, 385
Ferula sumbul 160 Irrigation of fruit trees 411
Fever bark 339 Islands of Calif 20
Fever bark. Australian 2.44. Islands, tropical 58
Fiber, of llax - 84
Fiber plants 85 .Talap culture 92
Flax culture 364 Jamaica cinchona 283
Flax seed 84 Jamaica ginger 99. ion
Flora. Calif 38, 173 Japanese drugs 104
Flora. Calif. Islands 26
Flora. Cntallna Islands 2S Kalmla latlfolla 183
Flora, of parks 3 Kansas med. plants 40
Flora, of San Francisco 10, 34, 35 Kelps 1
Flora. St. Lucas 24 Kelps, edible 168
Flora, western 16( King's Dispensatory 213
Flora. Yosemlte 33 Klamath Indians 66
Flowering plants 60
Food plants. Australian 219 Laboratory desert 63
Food plants. Indian 143 Laurel. California 145
Fruit garden 61 Lavender culture 74. 242
Fruit growing ■JS" Leaf hairs 21
Fruit hybrids 2il leaves, medicinal 325
Kmlt tree irrigation 411 Lintrls odorntlsslma 239
Fruits 352, 371 Licorice culture 289
Fruits, new 115 Lily of the Valley 130
Fumigation 3iS Llipildambar 282
Fungicides 38- Lohellaceae 31
Loco weeds 89, 307
Calls. willow 174 Lollum 114
Oarden 61 I os Angeles plants 76
Gardening 375, 381, 393 Lycopodium clavatum 228
(iarrya fremontll 295 Macaroni wheat 390
Gelsemlum sempervlrens 93 Manlhot alpl 388
Germination of seeds 303 Marah murlcatus 182
Ginger culture 188 Marie algae 1, 168, 318
Ginger. Jamaica 99. 100 Mariposa County 57
Ginseng 209. 312 Harrohlum 290
Ginseng. American 253, 312 Materia medlca 72
Glaucium flnvum 102 Medicinal leaves 325
Glvcvrrhi/n culture 289 Medicines 87
Golden Seal 312. 302 Medicinal plants 71, 73. 75, 121.
Grapes, diseases of 27- 221. 298, 299, 300
Grlndella robusta 334 Med. plants of Argentine 238
Gum. meznult 240, 290 Med. plants of Calif 9, 118
Gum. sweet 282 Med. plants of Canada 301
Gums 208 Med. plants. Cherokees 97
Hngenla abysslnlca 109 Med. plant culture 353, 354
Iledera helix 140 Med. plants of Indians. .. .50, 98. 259.
Hemp culture 80 261, 315, 330, 337
J'HARMACEUTICAL REVIEW.
Med. plauts of Kansas 40 Plants, Australian 218
Med. plants of Mexico 293 Plants, Death Valley 65
Med. plants of Minnesota 400 Plants, economic 134
Med. plants of Michigan 332 Plants, edible 00
Med. plants of New York 203 Plauts. flowering 00
Med. plants of North Carolina. .. .321 Plants. indigenous 91
Med. plants of Pennsylvania 338 Plants, Mariposa County 67
Med. plants of Philadelphia 340 Plants, medicinal 71
Medicinal weeds 149, 392 Plants, of Mexico 131
Megarrhlza 144, 410 Plants, poisonous. .. .46, 47, 48, 49, 51
Mezquit 90 Plants, products of 245
Mezcpilt sum 240, 280 Plants of Santa Barbara 113
Middle Calif, plants 129 Platystemon 37
Mexican uied. plants 293 Poisonous Astragali 119
Mexican plants 131 Poisonous honey 179
Michigan med. plants 332 Poisonous plants 46, 47, 48, 49, 51
Mlcromerin douglasll 105 Poisonous plants, Calif 18
Migration of weeds 82 Polygonum 327
Milkweed nibher 302 Pomegranate 43
MhmiluH glutluosus 355 Propagation, plant 384
Minnesota med. plants 267, 400 Pun lea granatum 43
Mini 342 Pyrethrum 246
Mint culture 74, 242, 331
Mushroom culture 309 (Julnlne sulphate 185
Mushrooms 249
Myrtles 224 Uape 157, 220
Kape culture 387
New fruits 115 Red clover 124, 275
New York med. plants 203 Kesins 208
North Carolina med. plants 320 Bhamul, structure of 116
Nutrition of plants 415 Khamnua 297
Ngal camphor 135 ithnmuus Californlca 29
Khamnua species 110
oaks 335, 359 Khododendron occldentale 349
nil of birch bark 184 Rhubarb, cultivation 56, 312
nil of wiutergreen 184 Rice culture 294
( >!ea 4 Rose culture 376
olen bark 339 Rose oil 294
(Hive 4, 399 Roses 305
Olive culture 273 Rubber, milkweed 302
(Hire ol! 352 Rubber plants 314
Onion i—lture 36u Rubber tree 361
Ouium. .American 122 Kumex hymenosepalus 257
opium. Calif 220
(niln™ Persian 23." Sabal serrulata 285, 322
Opuntln 02 Saffron culture 140, 2(15, 248
Sage culture 74, 242
Oie<Hla;ihne Californlca 145 Salix galls 174
San Francisco Bay plants 128
Panamlnt Indians 64 San Francisco drugs 330
Parasites, plant 38- San Francisco flora 35
Park flora 3 San Jacinto Mts 133
Parks, San Francisco 3 Sassafras 281
Pawpaw 177 Santa Barbara flora 113
Pawpaw culture 189 Santa Catallna islands 28
Peanuts 136, 303 Saw palmetto 322
Pennsylvania med. plants 338 Schinus molle 209
Peppermint culture 331 Seasons, wet and dry 234
Pepper tree 209 Seed of flax JJ4
Perfume plants 310 Seed germination 303
Perfumes 110. 304 Seeds 2.4
Persian opium 2i.> Seeds, oil producing ]•>'-
Pests, of drugs 336 Shrubs 1^1
Pharmacy. in California 40,> Sueexeweed
Pharmacy, Chinese 350 Soap plant 348
Philippine med. plants 340 Soli I"9
Pineapple 291, 379 Soli drainage 391
Pines . 13 Soil ferments 413
Pines of California 333 Soil fertility 3'3
Plant breeding 400. 401 Soil preparation >00
Plant culture 300 Soil sterilization ••.>-'
Plant dietary 00 Sonora gum
Plant lore Sorghum culture •<»'
Plant parasites 38- Southern vanilla
Plant products 411 Snrnvtng 3M.
Plant propagation '84 Sterilization of soil JTV
riant variation 401 SlrawU'rries 3"4
i
Sugar 358 Vegetable alkaloids 178
Sugar beet 369 Vegetnble liber 85
Sugar industry 321 Vendors, of drugs 200
Sumbul culture 100 Veratrnm, constituents 343
Survey of Calif 38 Viburnum species 227
Survey of Mexico 94 Vlgnn sinensis 374
Swampy Cree Indians 107 Viola tricolor 195
Sweet gum 2N2
Symbiosis 114 Weeds 81, 82
Sweet potato 377 Weeds of Colorado 70
Synonomy 215 Weeds, extermination 81
Weeds, loco 89
Tannin plants 210 Weeds, medicinal 149, 392
Taraxacum culture 390 Weeds, migration 82
Tes 208 West American flora 27, 32
Ttaea vlrldls 200 Western flora 167, 170
Tobacco culture 408 Wheat, macaroni 390
Tobacco curing 410 Whooping cough 53
Trees 181 Wild flowers, Calif 2(1i
Trtchome structure i ■ \4 21 Willow galls 174
Trlfollum 124 Wlntergreen oil 184
Tropical islands »8
Yerba bnena 105
I". S. Dispensatory 83 Yerba mansa ■' 211
Yerba santa 402
Vanilla 155 Yosendte flora 33
Vanilla culture l'l
Vnnllla. southern 2.!9 Zingiber 99. 100
Vanillas 19 Zingiber culture 188
Variation, in plants 401 Zygadenus fremontll 324
240 PHAUXIACEL TICAL UEVIEW.
By /. W. ISramM.
OILS OF THE MYRISTICACEAE.

120, 121. Oils of the Mace and Nutmeg. G.-H.-K., p. 366.
According to Thoms1" myristicin, C12H14O3 is l-allyI-3-4-
methylenediox5--5-methoxybenzene the corresponding iso-myristicin,
having a propenyl group in place of the allyl group, was prepared.
M. p. 44°—45°.
Allen and Brewis20 define as a normal oil of nutmegs one whose
constants agree with Ph. Germ. The B. P. 1885 and 1898 give
requirements for an oil from which myristicin, C1aHnOg, has been
removed and has an intense odor of mace. The authors claim that
the crystalline residue from the oil is not myristic acid but myristicin.
The oil with the later has a more powerful odor.
In the Germ. Ph. IV, the name mace oil applies to oil of nutmeg,
and not to the oil from the aril of Myristica frugranfi. The oil is
required to have dis°=0.890—0.930, and to be soluble in 3 parts
of alcohol.
Oil of mnce is official in the Swedish Ph. VIII; dis° = 0.855 to
0.930; a„ = dextrogyrate; soluble in 3 parts of alcohol.
The oil which satisfies the B. P. requirements is not the oil as
distilled from nutmegs, but an oil fractionated so as to exclude the
heavier portion. 21
OILS OF THE MONIMIACEAE.

122. Oil of Soldo Leaves. G.-H.-K., p. 368.
According to Aubert22 boldo leaf oil has sp. gr. at 22°=0.9189;
nD 24° = 1.471; soluble in 1 volume of HO p. c. ulcohol.
l» Ber., a0, p. 8446.
a«' Chem. & Vrugg., 5K, u. 485.
»i Analyst, 26, p. 29.
" Journ. Amer. (.'hem. Soc., 24, p. 691.
PllAKMACEUTICAL REVIEW. 247
OILS OF THE LAURACEAE.

128. Oil of Camphor. G.-H.-K., p. :i70.
Origin. According to Tuchirch and Shirasawa24 oval oil cells
are rapidly formed in the early period of the growth of the camphor
tree, and drops of a colorless very volatile oil are secreted into
them. Camphor is a transformation product of this oil. The vapors
of the oil penetrate throughout the plant and collect especially in
the cavities of the wood, being then changed into camphor.
According to Baker2a the cultivation of the camphor tree in
Florida, and the production of camphor from it, is likely to prove a
profitable substitute for orange cultivation. Only the leaves and
small twigs are distilled, seventy-seven pounds yielding one pound
of camphor. Cuttings can be made at least twice a year.
Although the manufacture of camphor from the wood, twigs etc.
dates far back, the production of camphor from camphor oil is more
recent. In 1876, a Japanese Wakichi Ono25 in trying to improve
camphor oil, which had always been used by the natives for lighten
ing purposes, accidentally discovered that it contains large quantities
of camphor.
Properties. Camphor oil is classified as crude oil, white oil,
and red oil.26 White camphor oil is obtained from the crude oil by
fractional distillation, after separation of the camphor. It is a
colorless oil, sp. gr. 0.87—0.91; b. p. 150°— 195°. It still contains
from 3 to 8 p. c. of camphor, besides pinene, phellandrene and
dipentene.
Red camphor oil is the fraction of camphor oil boiling higher
than camphor. It is a dark brown oil, sp. gr. 1 to 1,035; b. p.
225°—270° and consists chiefly of safrol, eugenol and a very small
quantity of camphor.
« Druifg. Clrc.. 11)02, p. 180.
™ Arch. d. Pharm.. 240. I). 257.
™ S. & Co., Rep.. Oct.. 11)02. p. 17.
»« Journ. Pharm. Soc. Japan.. 1902, 1>. -; S. Jfc Co.. Rep., Oct. 1902. p. 17.
(To he continued.)
2+8 PHARMACEUTICAL REVIEW.
Coniferous Oils of the Northwest.
iiy /. W. Bvn'uiM.
The attempt which is being made by the United States Depart

ment of Agriculture to reclaim the logged-off timber lands of the
United States for agricultural purposes, by obtaining from the now
valueless products upon the land, some substances of sufficient com
mercial value to equal the cost of clearing, has led the writer to the
study of the volatile oils from the leaves, wood and stump roots of
the various coniferous trees of the northwest. A series of reports
will be made on the results of this study.
1. Oil from the Leaves of Red Cedar.
By Albert H. Dewey.
The red cedar, or the canoe cedar as it was called by the Indians,
is a Conifer officially recognized by the Department of Agriculture
as Thuya 1ilicata, commonly known as Thuya gigantea (giant cedar
or Thuja), and named after the naturalist Menzies, who first des
cribed it as Thuya menziesii. Its habitat is the Pacific coast from
southern Alaska as far south as Mendicino County, California. In
Washington and Oregon this tree is so abundant as to form a
source of the great red cedar shingle industry. It is usually found
scattered through fir, spruce or hemlock forests, though sometimes
alone, and is very widely distributed.
The leaves and twigs of this tree yield upon steam distillation
from 0.8 p. c. to 1.4 p. c. of a volatile oil. The leaves from the
small trees and underbrush give the larger .yield. The material
distilled was identified as Thuya plica tn by Dr. T. C. Frye of the
University of Washington. The oil has a light yellow color and a
characteristic odor, slightly pungent and camphoraceous, yet
fragrant and pleasant. The following physical constants were found :
d2s° = 0.9a05; «i> at 25° = —6.9°; acid number 0.518; saponifi
cation number 5.7; acetylation number 6.2: soluble in all propor
tions in 70 p. c. alcohol.
The oil was fractionated into fractions of five degrees each and
then refractionated, as shown in the following table:
Boiling point. Volume. Sp. gr. at 25°.
—l0() 5 c. c.
160-165 4 c. c.
165-170 7.5 o. c.
170-175 11 + 75.8°
175—180 22 +72.5°
180—185 29 .. + 61.2°
185-190 40 +48.9°
190-195 91 'i 0.9039 +32.8°
195-197.5° 114 It 0.9113 +24.7°
197.5-198.5° 100 tI 0.9163 +31.6°
198.5-199 97 II 0.9170 +32.1°
199-200 124 II 0.9191 +42.6°
200—203 124 (t 0.9201 + 53.7°
20,*!—205 29 t. + 62.3°
205-210 23.5 t . + 68.5°
210—215 10 II +64.8°
215-220 5.5 It +58.5°
220- 60. It dextro.
From the above table it can be seen that from 896.5 c. c. of oil
distilled, 650 c. c. or about 75 p. c. boiled within thirteen degrees.
That this fractionation was relatively accurate, may be assumed
from the fact that a distilling column of half a meter in length was
used. While the optical rotation of the original oil is laevogyrate,
6.9°, every fraction of the oil is more than 24° dextrogyrate. The
cause of this change is at present being studied.
The oil is comparatively free from terpenes as shown by the
fact that only 27 c. c. or about 3 p. c. distilled over below 175°.
The fraction below 160° contained pinene (nitrosochloride m. p.
103°). The fractions below 185° were treated with metallic sodium,
allowed to stand a few hours, .filtered and refractionated. Fraction »
175°—180° of this distillation was tested for cymene by oxidizing
with dilute potassium permanganate, a small amount of a crystalline
substance, m. p. 121° being obtained. Oxycuminic acid melts at
155°.
While apparently no sodium bisulphite addition product could
be formed with a petroleum ether solution of the original oil, it was
believed that the bulk of the oil was a ketone. For this reason, all
the fractions between 190° and 203° in the original fractionation

were tested for tluijone, by t he preparation of the bromine derivative.
Fraction 190°—195° and fraction 200°—203° reacted very violently
and absorbed a great deal of bromine, while the intermediate frac
tions absorbed less and reacted less vigorously. From all the frac
tions treated, however, a crystalline derivative was obtained, which
after purification and recrystallization from ethyl acetate, melted
with decomposition at 120°— 121°. This corresponds to the melting
point of tluijone tribromide.*
In spite of the fact that the fraction 1 90°—1 95° absorbed a
large amount of bromine only a small amount of the tribromide
was obtained. The amount of tribromide increased with each suc
ceeding fraction up to 200°—203°. From the large amount of
bromine absorbed and the small amount of tluijone tribromide ob
tained, the presence of fenchone which yields only an oily bromide,
was suspected.
Because tluijone and fenchone are difficultly separated by frac
tional distillation, fractions 190°—195° and 195—197.5° were boiled
with dilute sulphuric acid to convert the thujone into isothujonet
which boils at 231°. Upon fractionation of the oil thus treated, a
small amount boiled from 225°—231°, but most of the oil came
over at the same temperature as the original fraction 190°—197.5°.
The oxime obtained from this fraction melted at 162°. The oxime
obtained from the original fraction 190°—195° without removing
the thujone melted at 152°. Fenchoxime melts at 164°—165°. t
The six fractions from 190° to 203° were dissolved in alcohol
and shaken with a freshly prepared saturated solution of sodium
bisulphite in' a shaking machine for 10 hours. After standing for
24 hours, the crystalline derivative was filtered off, washed with
alcohol and decomposed with dilute soda solution. The regenerated
oil boiled at 203°, thus identifying it as thujone. Since fenchone
.does not combine with sodium bisulphite, an oxime was prepared
from the fraction 190°— 195° which had been trented with sodium
bisulphite to remove the thujone. The oxime melted at 164°. This
oxime, together with the oxime prepared from the same fraction
after removing the thujone by converting it into isothujone, identi
fies this ketone as fenchone.
• WHllach: Ann., 27.1, p. 179 gives m. p. as 121°—1 2l>°.
t Waliach: Ann., 286, p. 101.
t Wallach: Ann., 20:!, p. 181.
PHARMACEUTICAL RE VIEW. 251
The residue boiling above 220° undoubtedly consisted largely of

esters of borneol, judging from the high saponification number of
this fraction,* and the fact that by oxidizing the saponified fraction
with nitric acid a small amount of a white compound was obtained
which. after purification by precipitation from alcohol, melted at
167°. Camphor melts at 175°.
A portion of the original oil was dissolved in alcohol and treated
with metallic sodium to reduce the ketones, thujone and fenchone to
their respective alcohols. The purified oil was then acetylized and
saponified. The acetylization number was found to be 96.833 which
correspond to about 28.5 p. c. of alcohols. This of course includes
borneol and the alcohols from fenchone and thujone.
Further work on this oil is now in progress.
University of Washington,
Departmfnt of Chemistry.
* Not detvrmlnnl exactly necuuxe of dark-red color ol oil.
The Apothecary. A Literary Study.
By Edward Kremers.
III. Knssmaul, Jugenderinnerungen eines alt en Arztes.

Of tins book its reviewer in ''The Nation"* states that it is a
"valuable contribution to the evolution of academic instruction and
scientific research during the first half of the 19th century."
Because of the interdependence of medicine and pharmacy, the writer
had hoped to find matter of special pharmaceutical interest. While
disappointed in this particular, he has been more than repaid by
reading it. Though every thing touched upon is related in one way
or another to the author, the personal side is never projected so
as to make itself unduly felt.
The absence of an account of the condition of German pharmacy
becomes all the more striking when we learn that a cousin of the
author was an apothecary, and that the father of one of his best
friends was likewise an apothecary. The several references to
pharmacists are, however, not without interest, and may here be
enumerated.
The first reference takes us back to his boyhood days when with
considerable relish he ate green apples while lingering on his way to
and from school. The apothecary who cough t 'him at it told him
he would be taken sick with diarrhoea, but he adds "Wir blieben
ganz gesund." The lad's esteem of the knowledge of the apothecary
evidently was not hightened by this experience.
Having received money from his father to take a trip into the
Black Forest, he straightway went to Baden-Baden and lost it at
roulette. "Arm am Beutel, krank am Herzen," he and his companion
walked to Buehl, where they called on a friend whose father was an
apothecary, with the hope of obtaining money. The apothecary
was turning pills and received the "Corpsbriider" of his son rather
• Vol. 74, p. 810.
PHARMA CEVT1CAL REVIEW.
coolly. His estimate of his son apparently was not very high, so
that his son's friends who had lost their money at Benazot was no
better. Evidently a pool, calculating business man, without apprecia
tion of youthful sentimentalism.
They next wandered to Rechen, which also had an apothecary
shop. Its proprietor was the author's cousin. He received them
cordially and not only gave them the desired money, but invited
them to stay as his guests.
In the chapter devoted to von Chelius, Professor of Surgery at
the University of Heidelberg, he relates a story about a Wurttem-
berg apothecary who had been in California. Here he had prescribed
pills as well as made them, and in his old days he had returned to
his fatherland to study surgery under Chelius. Like *o many
apothecaries in literature, he was "etwas verschroben."
Writing of his natural scientific studies at the university, he
mentions the .'a. o. Professor Dierbuch, ein altes bescheidenes Mann-
chen (geb. 1788, gest. 184.".). Erlehrte seit 1817 an tier Hochschule,
war ursprunglich und wesentlich Pharmaceut und ein grundgelehrter
Botaniker, mit der Medizin praktisch jetloch nieht vertraut. Er hat
eine Flora apiciaria (Flora fiir Leckenniiuler) und eine Flora mjrtbo-
lofria verfasst. Die nusser Ciebrauch gekommenen Kriiuter waren
ihm die interessantesten untl die Frage, mit welchem Oel sich die
Hexen beim Walpurgisritt eingerieben ha ben mochten, fiir ihn ein
(iegenstand ernster Erwiigung. Er eutschied sich fiir das griine
Bilsenkrautol."
We have here an illustration of the role pharmacy played in the
development of botany during the first half of the 19th century. It
is of interest to note that the humanizing of the science appenled to
the pharmaceutical professor possibly more than its latest develop
ment. Though a very good teacher and an excellent botanist, he
also is described as slightly "verschroben." It should be emphasized,
however, that in this respect he compares favorably with many of
his non-pharmaceutical colleagues.
When we learn that the author fell in love with his future wife
in an apothecary shop belonging to the father of a personal friend,
we can scarcely forgive him for not having recorded in detail his
reminiscences of the apothecary shops and their owners with whom
he must have been more or less intimately acquainted.
254 PHA RMACEUTWAL REVIEW.
Literary.
Books Reviewed.
DlSPENBATOBIUM PRO PHABMACOPCEIS VIENNEN8IBUS IN AUSTRIA ex
mandate sac. eaes. mtntis a collegio medicomm viennensium
collectum et revisum. Das iilteste Wiener offizinelle Dispensier-
buch vom Jahre 1570. Naoh der Urschrift im Archive des'
Wiener Medizinischen Doktoren-Kollegiums. Mit Uuterstutzung
des Wiener Apotheker-Haupt-GreminiuH. Zum ersten Mai her-
nusgegeben und einbegleitet von Dr. Leopold Sen f elder. Ein
Bd., pp. XXXVII, 204. Verlag von Franz Deuticke in
Wien. 1907. M. 7.00.
In the present revival of interest in historical matters, medical
as well as pharmaceutical, the pharmacopoeias of the past will un
questionably play an important role. As a contribution to this
branch of historical literature we welcome the publication of this
hitherto imprinted local dispensutoiy. If pharmacopoeias are images
which reflect the times in which they have been written we do well
in going to them for the study of the past. But even a photo
graphic image may be distorted because of an imperfect lens. More
over, a pharmacopoeia can be but a partial image and must be
studied in the light cast upon it by the general conditions of the
times in which it was compiled.
Fortunately this light has been supplied, in part at least, by
the author. How modern some of the revelations seem. We are in
formed that the apothecaries of Vienna in the sixteenth century
were in the habit of making up preparations according to their
private formulas, each charging such a price as suited his own con
ditions. Such a state of affairs was a decided inconvenience to the
medical practitioners. The medical faculty, therefore, expressed a
wish for like formulas and uniform prices. One of the more public
spirited apothecaries arranged a love feast at which physicians and
apothecaries discussed the subject. The following day the apothec
aries sent an official request to the medical faculty asking it to pre
PHAKMACEUTICAL REVIEW. 205
pare 11 dispensatory which they promised to follow. The medical

faculty in turn requested the apothecaries to submit an alphabetical
list of all "composites" and — this is not likely to be duplicated
nowadays — invited the apothecaries to a banquet. Four days after
this second feast the apothecaries handed in 'such a list.
Here the good work seems to have ended for in the same year
the friendly relations between the two callings came to an end be
cause of the quackery of some of the apothecaries who were not
organized properly. The strong hand of organization, therefore,
could not make itself fealt, neither did the government interfere.
Sixteen years later, however, pharmaceutical matters were regulated
by imperial edict. More than three hundred years ago, therefore,
it was as true as it is to-day that if pharmacists themselves do not
properly regulate their own affairs they will be regulated for them
from without. Thus the first Vienna pharmacopoeia was prepared
by the Medical Faculty in accordance with orders from above rather
than by cooperation with the apothecaries.
A list of the classes of preparations may here be given. A dis
cussion of individual preparations — interesting as this might be —
is out of the question. The numbers in parentheses refer to the
numbers of preparations in each class.
I. Electuaria et confection™ animatioa' corroborantes. (1—16.)
H. Confectiones opiatie. (47—51.)
IH. Conservie usitatores. (52—72.)
IV. Condita. (73—98.)
V. Species sivo pulveres. (103—111.)
VI. Film odoratie. (112—113.)
VII. Ue syrupis. (114—166.)
VIII. De Julep et succis medicatis Rob appellatis et succis inspissatis.
(167—180.)
IX. Decoctiones. (181—189.)
X. Eclegmata sen Lohoch. (190— 198.)
XI. Electuaria alvum lenientia et■ purgantiu. (199—226. 1
XII. Catapotia sive Piluhe. (227—253.)
XIH. De Trochiecis. (254—285.)
' XIV. De Collyriis vel Sief. (286—290.)
XV. De Oleis. (291—337.)
XVI. De Unguentis. (338—376.)
XVH. De Kmplastris. (377—391.)
XVIII. De Ceratis. (392-394.)
Then follows a catalogue of necessary simples: /. Herbm et folia ;

II. Flores; III. Sem imi ; 71'. Fructue ; V. Radices; VI. Succi et
lit1 u ores; VII. Olea ; VIII. Gummata; IX. Cortices et lis ndna-
sentia ; X. Ligna ; XI. Ex nninumtibus integra. ; XII. Partes;
XIII. Pinguides; XIV. Medulla;; XV. Ossa; XVI. Excrementa;
XVII. Sanguis; XVIIf. E terra mineralia ; XIX. Lapides et Gem
ma'; XX. Terrie ; XXI. Ex mari et nquis.
An alphabetical index of the composites concludes the work.
How complex some of these composites are may be seen from a
relatively simple illustration, viz. the lrochisci di> Term sigillata.
li. Sanguinis Dracouis, Gummi Arabici assate,
Trochiscorum Bamich, Kosarum rubear.,
Sem. rosarum, Amyli assati. Spodii,
Acacia>, Hypocystidis, Balaustiorum, Boli
Armcni, Terra' sigillatie, Curallii rubri,
(Jamba. una tlr. II.
Margaritaram, Tragacantbie, Papaveris
nigri ana dr. I. S.
Sem. Portulaca?, Coinu cervi usti, Tburis,
liallarum Cupressi, Croci ana dr. II.
Aquae Plantaginis q. s. fiaat trochisci.
As supplement a price-list is published, viz. a Taxh vendicionis
medicinarum for the upothecaris of Vienna which possibly antedates
the year 1454. In addition to the historical introduction, the author
has provided brief explanatory notes on the drugs, also two alpha
betical indexes, one Latin, the other German.
If pharmacy is in danger of being commercialized, this tendency
can not be held in check better than by the revival in the studies
of the past of our calling. The Vienna "Apothekcr-Haupt-Gremium"
is to be congratulated, therefore, upon the success of this publica
tion which it has supported financially. May the good example it
has set find imitation with many other pharmaceutical organiza
tions. E. K.
Volume 26. SEPTEMBER, 1908. Number 9.
Editorial.
The first and subsequent meetings of the Association of

State and National Pood and Dairy Departments were
given but scant if any attention by the pharmaceutical press of this
country. Its name is not at all suggestive of matters pharmaceuti
cal. Why, therefore, should the twelfth annual convention held at
Mackinac Island August 4—7 receive special notice in a pharmaceuti
cal journal? To any one who has read the signs of the times, and
particularly to one who was present at this last meeting, the reasons
are very apparent.
Unfortunately, and to the discredit of American pharmacy at
large and of our state boards in particular, it must be admitted
that certain powers and duties with which the latter had been
entrusted since their establishment twenty-five years ago and more,
have practically been taken away from them. Like in the subject
of pharmaceutical education, so in the control of adulteration, the
druggists, especially as represented by state associations and state
boards, have been found wanting. The druggists of this country
are just learning that the food and dairy commissions of the several
states are not all political sinecures and that to the control of food
stuffs and dairy products have been added drugs in the broadest
sense of the term.
The clamor in" certain states that the control of drugs be taken
away from these commissions, and also from boards of health, and
be returned to the boards of pharmacy will not meet with a willing
ear on part of the public, especially since the extent of deficient
drugs and medicaments has been revealed by the chemists of these
commissions and boards. The better educated druggists of this
country will have to realize that first of all they must show them
selves more than willing to do away with the incompetent and dis
honest competitor, as well as with deficient drugs, before they can
(357)
regain, and then possibly in part only, the professional independence

which they formerly enjoyed.
If one reflects upon this situation for but a moment, is the well
nigh total absence of pharmaceutical representatives from the
Mackinac meeting not a bit surprising? Where were e. g. the ever
eager representatives of the drug press? Are the personal items
about druggists and their friends more important than a paper on
"The deterioration of some standard pharmaceuticals", simply be
cause the latter was presented by a Food and Drug Commissioner?
Are the records of sporting contests and guessing games at our
state association meetings worth the paper on which they are
printed when a number of papers on pharmaceutical matters are
presented at the annual meeting of Food and Dairy Departments
with scarcely a word of comment?
It is true that Dr. Fischer was active at Mackinac for the greater
part of two weeks on the Joint Food Standard Commission, how
ever, not as Professor of Pharmacy, but as chemist of the Wisconsin
Food and Dairy Commission. It is likewise true that Professor
Rusby and Dr. Kebler were on the programme with pharmaceutical
subjects, though not present to present them, but again not as
representatives of pharmacy, but as officials of the Department of
Agriculture at Washington. The jobbers, it is true, were represented
by their General Representative, Mr. F. E. Holliday.
But what can pharmacy as a calling do? When more than a
year ago the writer directed the attention of the Council of the
American Pharmaceutical Association to the humiliating fact that
the Council of One Hundred contained not a single representative of
pharmacy though all other callings, even the ministry, seemed to
be well represented, he did not expect that our national organization
could force itself upon this body which had been organized to
advance national and local hygiene. It may not be practicable to
attempt to do something at once in bringing about better relations
between the national organization of Food and Dairy Departments
and the representative national pharmaceutical organization, the
American Pharmaceutical Association. However, that the latter, as
the truly representative organization of American pharmacy should
take cognizance of the situation there can be no doubt. This much
ought to become apparent from the following considerations.
Touching upon the work of the Standards Committee, President
Ladd in his annual address made the following significant state

ment :
"The establishment of standards for foods, beverages and drug products,
not Official at the present time, should be carried forward to completion
as rapidly as possible.''
No doubt, the pharmaceutical as well as the medical profession
will welcome the cooperation of all chemists, including agricultural
chemists, in such an effort. Indeed some of these chemists, both
because of their previous pharmaceutical education and their
experience as public analysts are especially qualified to assist in this
important work. But is the American Pharmaceutical Association
as the representative of pharmaceutical progress willing that this
work be taken out of its hands and placed with food and dairy
commissions, no matter how capable and honest their representatives
may be?
The number of papers on pharmaceutical subjects read at
Mackinac clearly reveals the fact that the food and dairy commis
sions have begun to take the drug aspect of their work seriously.
Whereas, formerly at least, some of them were reluctant to take up
this new feature, the inclination at present seems to be to make the
most of it. This change of sentiment at the present time on part
of some, if not many of the state commissions, will be better under
stood when we remember the impetus given to the movement by
the National Pure Food and Drug Law since its enforcement some
what over a year ago.
•W.hite-we may welcome this new manifestation of activity on the
part of the food commissions, since it will unquestionably lead to
something better in pharmacy, the present time seems unfortunate
for cooperation. Possibly the writer is mistaken in this. He hopes
that, in spite of what he has seen and heard at Mackinac he may be.
But why should cooperation present any difficulties whatever?
Why cannot the American Pharmaceutical Association invite the
Association of State and National Food and Dairy Departments to
send a delegation to its annual meetings and, likewise, send a delega
tion to this new organization for the purpose of considering topics
of common interest? Or, better still, why cannot the two organiza
tions cooperate as do the American Medical Association and the
American Pharmaceutical Association in the Section of Pharmacol
ogy and Therapeutics, or in the Council of Pharmacy and Chemistry

or the former body?
There ought to be no inherent difficulty theoretically, especially
since more than one of the food chemists still is or has been associ
ated with pharmacy. Yet a practical difficulty has arisen. The
Association has decided to do all of its work, save the mere reading
— this term in this instance must be taken literally and does not
include discussion — of papers, in executive session.
On this subject the President made the following recommenda
tion in his address. He said:
"The time has come when this body should, in my judgment, be more
of a deliberative body than it has been in the past. To that end the Exe
cutive Committee have arranged that one-half of the time of the present
convention be given to executive sessions. Morning sessions in general
should be given up to deliberations of interest to the Food Commissioners
and their Chemists held in Executive session. All discussions of paptrs
should be in Executive session when the fullest and freest expression may
be had as to the best methods of dealing with important problems, and
when real progress can be made in harmonizing the work under the many
state laws. When thought desirable competent individuals not members of
the Association, could be invited to address the Executive session or to
discuss some features of papers already presented."
In accordance with this sentiment, the Executive Committee had
previously arranged the programme, and, after a day's trial — so
an officer of the Association informed the writer — the Association,
in executive session assembled, voted to continue the highly satis
factory arrangement.
That the food and dairy commissioners have innumerable
matters to discuss which are best talked about in a room from
which the general public is excluded will appeal to all reasonable
persons. That the scientific papers read by the chemists of such
commissions should be discussed behind closed doors seems so
strange at first that it is wellnigh incomprehensible. Yet the writer
attended an open session at which eight papers were read, applauded,
and handed to the stenographer, but not a word criticism, con
structive or destructive, was utteed. The discussion, as was learned
later, was left to the next executive session.
Scientists who are not accustomed to such a procedure will have
to be reminded of a very important fact, viz. that the large bulk of
the work of the state chemist, while it is intended to reveal the truth,
is not done in order to ascertain the truth for its own sake or for
any scientific purport, but is undertaken "with a view to prosecute."
Moreover, the experience of the Association has shown that out
siders ofttimes practically monopolized the discussion, and that the
press equally often misrepresented the statements made by its mem
bers in open discussion. Undoubtedly, the Association made a mis
take when in the past it allowed Tom, Dick and Harry to vent their
ideas when courtesy ought to have made them more considerate and
and cautious. Bat whether the Association has not made an even
greater mistake by going to the other extreme remains to be seen.
Primarily the Association is not a private organization of profes
sion^ men, but a deliberative body of public officers. If Congress
did practically all of its work behind closed doors, the American
people would rise as a body and demand publicity. If the request
from an officer of the National Consumers League, viz. that the
Association consider the advisability of asking for a repeal of the
tax on olemargerine causes but laughter when read in open session,
the public may some day want to know whether the food and dairy
commissions are maintained by the respective states for the pro
tection of the farmer or for the protection of the people at large.
If for the latter reason why must such matters be discussed behind
closed doors.
We may fully appreciate the annoyances to which the members
of the Association have willingly subjected themselves during the
past, we may also appreciate somewhat the annoyance of a situation
when one member advocates as the only right way a measure which
another member from another state has repeatedly condemned as
all wrong. We can even understand, because of the past, why in
private conversation a member of this organization should shrink
from a discussion of his paper that ventures beyond a conventional
complimentary remark. But all of these signs are manifestations of
morbidness which the Association must overcome, the sooner the
better.
Giving the Association full credit for the good work it has done,
it will become apparent why cooperation with such a body of men,
that suspects private interests and undue influence at every new
contact, will be difficult. For this the Association is not alone to
be blamed. We as pharmacists should be willing to shoulder our
part. In past years, when the question of a national pure food and
drug law came up periodically at Washington, we, only too often,
allowed men to represent us at these conferences who were secret
nostrum manufacturers rather than representatives of legitimate
pharmacy. It will not be easy at present to right the situation ;

but cooperation in the establishment of non-official pharmaceutical
standards should be brought about at once, possibly best through
a joint committee'. For such a committee the time seems specially
opportune, for President Ladd in his address pointed out the
necessity of the enlargement of the Committee of Standards and the
organization of such a committee into sub-committees to which
special divisions of labor might be assigned. Such a committee on
non-official pharmaceuticals could well cooperate with a like com
mittee of the American Pharmaceutical Association, and possibly
another committee of the American Medical Association.
As pointed out at the beginning of this report, both state and
national food and dairy departments are assuming a decidedly
aggressive attitude in the matter of drug inspection. This we should
welcome under the circumstances, but having largely lost control
over this important aspect of professional activity, let us beware
lest we loose even the position of counsel in the establishment of
non-official pharmaceutical standards. From what the writer has
been able to learn, the best representatives of the Association of
State and National Food and Dairy Departments are not only
willing to cooperate with the pharmacist, but will even welcome him
if, in offering to cooperate, he strives after a legitimate and honorable
independence.
Of the forty-four papers read, the following are of special interest
to pharmacists, viz. :
2. "Enforcement of Food and Drug Laws,"' Honorable R. W. Dunlap,
Dairy and Food Commissioner, Columbus, Ohio.
17. "Inspection under the National Foods and Drugs Act," Mr. W. G.
Campbell, Chief Food and Drug Inspector, United States Bureau of
Chemistry, Washington, D. C.
22. "Inspection of Natural Products," Professor R. E. Doohttle, Chief,
United States Food and Drug Laboratory, New York City.
23. "The Deterioration of Some Standard Pharmaceuticals," Honorable
II. E. Barnard, Food and Drug Commissioner and Chemist, Indianapolis,
!nd.
24. "Plant Products Under the Foods and Drugs Act," Dr. H. H.
Rusby, Expert in Plant Products of United States Bureau of Chemistry,
Washington, D. C.
27. "Drug Products,'' Dr. Lyman F. Kebler, Chief, Division of Drugs,
Bureau of Chemistry, Washington, D. C.
32. "Drug Inspection in Wisconsin," Dr. Richard Fischer, Chemist,
Dairy and Food Commission, Madison, Wisconsin.
33. "The New Kentucky Foods and Drugs Act," Dr. M. A. Scovell,
Director, Kentucky Agricultural Experiment Station, Lexington, Kentucky.
Percolation*
By /. W. Bramlel and Ed. Krenters.

Beck, 1895.
Percolating Stand.
Caspari-Treatise on Pharmacy, 1901, p. 144.
Fig. 43. Percolating Stand.

This stand admits of simultaneous multiple operations. It can be
changed by means of thumb screws to suit various heights of bottles. The
length of the base-board is 42 inches, the width 12 inches and the extreme
height of the stand 36 inches. The supports for percolators and funnels
are formed by means of cross pieces suitably hollowed out and secured by
screws passing through the slot in the cross bars.
Remington, J. P. Jr. 1901.

Apparatus Stand.*
Am. Jonrn. of Pharm., 73, p. 19.
A neat, convenient and easily adjust
able device for supporting percolation
apparatus. Two of the stands as shown
in the illustration can lie connected by
two parallel horizontal, double tubes ar
ranged so as to slide up and down the
upright tubes and made secure by thumb
screws at each end. An illustration of
such an apparatus is given on page 20.
The ring clamps instead of being all in
one piece, as in the ordinary stands, are
made in two parts, and therefore permit
of universal adjustment in three directions.
Fig. 44. Apparatus Stand.
Lloyd, J. U. 1904.
U. S. Patent No. 777.115.
An apparatus for
making extracts etc.,
whereby thesubstance
held in solution is not
changed by heat; by
which the alcohol or
other menstruum is
used over and over
again and in which
the menstruum re
maining in the waste
may he recovered.
Fig. 48. Lloyd's Percolator.

• Mmle by the Remington Mfg. Co., Philadelphia.
Lenz, W. 1905.
A hot-extraction and pressure percolator.
Ber. d. D. Pharm. Ges., 15, p. 1!J7. •
Fig. 4.6. Lenx's Percolator.

This jacketed percolator is specially designed to carry
on simple percolation at any desired temperature, by pass
ing hot water or steam through the jacket. The cover is
tight which prevents evaporation. The cover has three
openings, one for a thermometer, one for a pressure gauge
and the third is a Fahrrad valve through which a pres
sure of two or three atmosphere can can be maintained
in the apparatus by means of an air pump.
Bldred, F. R. 1906.
Assay percolator.
Journ. Am. Chem. Soc, 28, p. 187. [Proc. A.
Ph. A., 54, p. 59a.]
A small percolator for us:' in drug assaying. A plug
of cotton is packed tightly below the construction A.
The glass stoppers on both ends allow the drug and
solvent to be thoroughly shaken without loss, before
percolating.
Pig. 4.7. Bldred 'b Assay Percolator.
26(i PHARMACEUTICAL REVIEW.
Laboratory Exercises. Carefully select a percolator of such a size

bo as to be about % filled by the quantity of drug used. The choice of a
conical or cylindrical percolator, will depend upon the drug used, and the
nature of the menstruum and percolate.
A perforated cork, bearing a short glass tube should then be tightly
wedged into the funnel-end, from withm, until the end of the cork is even
with the- outer edge of the orifice. The glass tube must not extend above
the inner surface of the cork and should project about 2 inches beyond the
outer surface. To the end fasten a closely fitting rubber tube, about %
longer then the percolator itself. The rubber tube, the end of which should
contain a second short glass tube, may be clamped to the side of the per
colator during maceration by means of a rubber band, so that the end of
the tube is above the surface of the menstruum in the percolator.
To prevent the powdered drug from falling through the funnel-
end, place a notched cork, Fig. .18, in the neck and cover with a
thin layer of cotton; or a tuft of cotton above maybe used which
should be slightly pressed into the neck of the percolator. The
cotton should be moistened with a few drops of the menstruum,
bo as to aid in the passing of the first part of the dense per-
It is sometimes found convenient to place a thin layer of clean
white sand on top of the cotton to hold it in place. Care
should be taken not to press the cotton in too tightly. It
Bbould almost cover the bottom of the percolator with a
thin layer and fit loosely into the upper part of the neck.
Glass wool may be used in place of cotton. It has the ad
vantage of retaining its spongy condition on becoming wet.
Place the substance to be percolated, which must be uni
formly powdered and of the fineness directed in the formula,
iu a shallow dish, pour on the specified quantity of menstru
um, and stir thoroughly with a spatula until uniformly
moistened. This can usually be determined by the ubsenceof
lighter colored lumps. Pass the moist powder through a
coarse sieve, transfer to a sheet of thick paper and pour the
whole quantity from this into the percolator. The powder
should be shaken down lightly and allowed to remain thus
for ii period varying from a few minutes to several hours
according to directions. After this pack the drug uniformly
with a aid of a suitable plunger of the shape of the common
potato-masher, Kig. 49. If desirable, especially where larger
quantities of the drug are used, the powder can be introduced (.. r (;|
and packed in portions.
After the powder has been properly

packed, place a circular piece of filter
paper, slightly larger than the upper
layer of .drug, upon the upper surface
of the powder, weighing it down with
pebbles or glass stoppers, or with
weights especially made for ttos .pur
pose, Fig. 50.
Then gradually add a quantity of
menstruum, care being taken not to
disturb the powdered drug, sufficient
to completely saturate the whole pow Fig. SO.
der and to leave a layer above. Hav
ing covered the percolator with a rubber percolator cover
Fig. 52, or apiece of glass, allow to macerate for th e directed
time.
To start percolation, lower the rubber tube from the
side of the percolator, and introduce the glass end into a
tared or graduated bottle (Fig. 51) to receive the percolate.
The rapidity of percolation may be increased or decreased
by raising or lowering this receiver. A layer of menstruum
must be constantly main
tained above the powder.
Great care should always
be taken never to allow
the menstruum to disappear
below the surface of the Fig. 61.
Fig. 52. powder This prevents the
V
drawing of air into the interstices of the drug and the subsequent forma
tion of fissures, through which the menstruum would flow, instead of per
colating through the powder.
Fig. 53 shows two

percolators, A proper
ly packed and B im
properly packed mid
set up.
The exhaustion of
the drug can be deter
mined by a chemical
test for one or more
of the active con
stituents by tasting
or more rarely by the
color.
Prepare one or
more fluid extracts
and tinctures by the
method of percolation
as given above, re
cording the amount
of druR used, the
amountof menstruum
used, the amount of
percolate obtained,
the amountof finished
product, and the time
of actual percolation.
Compare method of
percolation as given
in U. S. Pharmaco
poeia, p. LI.
Fig. S3. Properly and Improperly packed percolator.

Bxerciae II. - Weigh out 32 parts of the drug in the official powder and divide into
Repercolation. 4 equal portions of 8 parts each.
Moisten one portion of the drug with the proper menstruum, t pack and
macerate (see Exercise I and U. S. P.) and percolate. Reserve the first 0
parts of percolate and continue the percolation until the drug is exhausted
separating the percolate received after the reserved portion into fractions
of about 8 parts each.
t The amount of menatnium used for moistening should be In the Hame pro
portion ELM given in the U. 8. P.
Moisten a 2nd portion of 8 parts of the drug with t he first fraction of

the weak percolate — the portion that was obtained next after the reserved
percolate—pack, macerate and percolate as before, supplying the percolator
with the remaining fractions of the weak percolate in the order in which
they were obtained, and finally with fresh menstruum until the drug is
exhausted. Reserve the first 8 parts of the percolate, and collect the weaker
percolate into fractions of about 8 parts each.
Percolate the Jtrd and 4th portions of 8 parts each of the drug in the
same way as the 2nd portion.
Finally mix the four reserved percolates together which would make 30
parts of finished fluid extract. Having corked, labelled and numbered the
bottles containing the fractions of weak percolate set them away until the
process for the same drug is to be resumed. When the same fluid extract
is to be made again, repeal the process as with the 2ud portion.
Apparatus:— The essential parts of a continuous percolation apparatus Exercise in.—
consist of a cylindrical percolator, a receiving flask and a condenser. An Continuous
Percolation.
apparatus can be readily constructed as shown in Fig.
54. A is an ordinary conical percolator of such a size
that it will not be more than two-thirds filled with
the drug to be extracted. B is a round-bottom flask,
containing a twice perforated stopper, through one
hole of which a glass tube connects the flask to the
percolator. Through the second hole is inserted the
glass tube f which also passes through the cork
stopper in the top of the percolator. The end of the
condenser D is also inserted through the latter cork.
All cork connections should be tightly sealed with
gelatine.
Method: — In extracting a drug, e. g. the pre
paration of an official oleoresin, pack the drug into
the percolator A as in simple, percolation (see Exer
cise I ) without previous moistening or macerating.
Pour on menstruum gradually through the condenser
tube, until about 50 c. c. has collected in the receiver
B and there still remains a layer of menstruum above
the drug in the percolator. Apply heat to the pre
viously warmed water-bath so that the menstruum
will distill through the tube C and back into the
percolator, when it will again pass through the drug Fig. 54.
Continue the percolation, regulating the rate of distil
lation so that it about equals the rate of flow of the percolate, until the
drug is exhausted. By carefully regulating the rate ot distillation, so that
some menstruum always remains in the flask B, overheating of the residue
is prevented.
With the above apparatus, prepare one or more of the official oleoresins.
Exercise IV.— The Soxhlet extraction apparatus differs from the continuous percolation
Percolation apparatus, described in Exercise III, in that it involves, in addition, the
Extraction*1*1*' aw principle of a siphon. The apparatus consists of a
Apparatus. cylindrical percolator, Fig. 55, in which the pow
dered drug is poured in loosely but not packed. The
top of the column of drug, upon which a circular piece
of filter paper should be placed, should be lower
than the top of the siphon. The menstruum is
poured through the condenser, and should be of
sufficient quantity to fill the siphon and leave a layer
of the liquid above the drug, higher than the top of
the" siphon. The siphon will then start to flow
and will continue until all the menstruum in A has
been siphoned into the receiving flask tightly fastened
to the end of the percolator by means of a cork. By
applying the heat of a water-bath the menstruum
will distill through the tube and will flow from the
condenser back into the percolator. When the
level oi the liquid is above the top of the siphon, per
colation will again take place, the liquid being again
siphoned into the receiving flask. This operation can
be repeated until the drug is exhausted. Prepare an
Fig. 55. oleoresin with the Soxhlet apparatus.
ERRATTA.
On page 31 Oldberg (1884) is given credit of first having suggested the
use of tall, conical percolators. These were in reality first suggested by
Diehl,* although they are still commonly known as the Oldberg percolator.
• Proc. A. Ph. A., 27 (1879), p. 727.
By /. W. Bramlel
Composition. From the fraction of oil, soluble in alkalies,

S. & Co. 27 have isolated carvacrol (phenylurethane m. p. 136°); a
phenol yielding a phenylurethane melting at 85°—95°; a mixture
of aliphatic acids, principally caprylic acid. A crystalline 1-terpineol
m. p. 35° has been isolated from camphor oil.28 It yields a phenyl
urethane melting at 112°. From the fraction 161°—164° isobornyl
ticetate was prepared, showing the presence of camphene. The
regenerated camphene melted at 50°.
According to Loehr29 safrol is found only in dark colored
Japanese oils which have sp. gr. ±1. The higher the sp. gr. the
greater is the safrol content. The camphor content can be deter
mined as follows:
The oil is divided into three fractions: —195°; 195°—220°; 220 +. The
second fraction which contains all of the camphor is kept in a freezing
mixture for one hour, the camphor filtered off and expressed twice between
filter cloth and then weighed. The nitrate is again fractionated and fraction
205°—220° is frozen and treated as before. This process is repeated several
times. Samples of oil were found to contain 19—21 p. c. of camphor.
The following patents for the production of artificial camphor
have been granted in various countries. The Ampere Eiectro-
Chemical Co.30 has made a commercial application of the following
patent :
5 parts of oil of turpentine free from water are heated to a temperature
below the boiling point, 120°—130° C., with one part of anhydrous
oxalic acid. The pinene unites with the acid to form pinene oxalate,
C10H17O.CO.COOH, a solid b. p. 157°—160° C. which decomposes upon
heating into camphor, carbon dioxide and water. The formic acid resulting
from the oxalic acid forms pinyl formate, a liquid b. p. 160°—163°, which
a? 8. & Co., Rep., Oct. 1902, p. 21.
2» S. & Co.. Kep. Oct. 1903, p. 16.
»» Chem. ZtK., 25, p. ; 292.
»o U. S. Pat. Eng. Pat. 14,754 [J. Soc. Chem. Ind., 20, pp. 67, 604;
21, p. 1469]; Pat. Kl. 12, Nr. 134,553 [Chem. Centnilbl., 73 II, p. 9(5].
decomposes into borneol and carbon dioxide. The reaction therefore pro
duces a mixture of borneol, its oxalic and formic esters, camphor and poly
merization products. The esters are decomposed with lime and the borneol
separated by distillation and then oxidized to camphor with potassium
dichromate and sulphuric acid. From 350 yarts of oil 100 parts of cam
phor are obtained.
Woodsa1 had worked out the following methods:
1. Pinenemonohydrochloride prepared by the action of gaseous hydro
chloric acid upon oil of turpentine, is purified by sublimation in a current
of steam and converted into solid eamphene by boiling with sodium acetate
and an alkali carbonate. The eamphene is oxidized to camphor with an
alkaline permanganate, chromate, or chlorate and very dilute sulphuric
acid.
2. Camphoric acid, formed by subjecting oils to the prolonged action
of hot air and steam, is reduced with nascent hydrogen obtained by the
electrolysis of the solution of camphoric acid or by adding zinc and sul
phuric acid.
3. Camphoric acid is boiled with three equivalents of eamphene in the
presence of sodium acetate or sodium formate, both eamphene and cam
phoric acid being converted into camphor.
The somewhat similar method has been patented by Magnier and
Brangier. 32
According to Semmler3a a much greater yield of camphor can
be obtained from isoborneol if the lattter is dissolved in glacial
acetic acid and the calculated quantity of potassium permanganate
added, than when treated with potassium dichromate and sulphuric
acid.
According to a patent by Stephan34 eamphene can readily be
prepared by causing ammonia to react upon the hydrogen-halide
compounds of pinene for a long time at a high temperature.
Processes for the production of eamphene have been patented by
Chem. Fabr. auf Actien.85
Schmatolla a0 has devised the following method to determine the
percent of camphor in spirit of camphor:
10 grams of the spirit are shaken with 30—35 c. c. of a saturated solu
tion of sodium chloride in a 50 c. c. burette graduated to 0.1 c. c. When
the camphor has collected on the surface, exactly 1 c. c. of petroleum ether
is added and the camphor dissolved by gently rotating the upright well-
si Apoth. Ztg., 1899, p. 661.

32 Fr. Pat., §17,804; J. Soc. Chem. Ind., 21, p. 1411.
»» Ber., 38, p. 8420.
»* U. S. Pat., 707,270, 707,271; J. Soc. Chem. Ind, 21, p. 1194.
3« Fr. Pat. 821,874, 821,851: J. Soc. Chem. Iud., 22, pp. 317, 828; — Eng.
Pat. 26,618; J. Soc. Chem. Ind., 21, p. 1558.
stoppered burette. After some minutes the volume of petroleum ether solu
tion is read off, the volume of petroleum ether deducted and the weight of
camphor calculated by assuming every 1.02 c.c. to be equivalent to 1 gram.
128. Oil of (Ceylon) Cinnamon.

Besides cinnumic aldehyde, eugenol and phellandrene, Walbaum
and Hiithig,36 have isolated several new compounds from oil of
Ceylon cinnamon. From the first runnings of the oil. methyl-n-amyl
ketone (semicarbazone m. p. 122-123°) CHsCOCH2CI^CH2CHaCHs,
and furfurol were isolated. The hydrocarbons pinene (nitrol benzyl-
amine m. p. 122°—123°), caryophyllene and cymene were identified,
and also benzaldehyde (phenylhydruzone m. p. 156°); nonylic alde
hyde; hydrocinnamic aldehyde (semicarbazone, m. p. 126°); cumic
aldehyde (cumic acid, m. p. 114—116°); linalol; linalyl isobutyrate.
A patent has been granted Schimmel &C0.a7 for the preparation
of an artificial Ceylon cinnamon oil by mixing cinnamic aldehyde
phellandrene, eugenol, n-amylmethyl ketone, nonylaldehyde, cuminic
aldehyde, caryophyllene, linalool, and linalyl isobutyrate.
Goldschmidt38 has prepared two oximes of cinnamyl ketone,
melting at 55° and 151°; the phenylhydrazone m. p. 147° and the
tetrabromid (C8H5CHBrCHBr)2C0.
Hanus39 has devised a method of determining cinnamic aldehyde,
quantitatively, by the formation of a crystalline semi-oxamazone.
0.5 to 2 grams of the oil are emulsified by agitation with 100 c. c. of
water. From 0.25 to 0.35 grams of semi-oxamazide, dissolved in 15 c. c.
of water is added to the emulsion and the mixture, after agitating
occasionly for 3 hours, is set aside for 24 hours. The precipitated cinna
mic aldehyde semi-amazone, is then collected on a tared Gooch filter,
washed with cold water, dried for 4 or 5 hours at 105° C., and weighed.
The weight thus obtained, multiplied by 0.6083, gives the amount of
cinnamic aldehyde present.
The Belgian Pharmacopoeia, 1903, recognizes the oil from
Cassia lignea*0 or from Cinnamonium Ceylanicum, requiring dis° =
1.050—1.070; soluble in 3 parts of 70 p. c. alcohol; 70 p. c. of
aldehyde.
3« Joum. prakt. Chem., 66, p. 47 ; S. & Co.. April 1902, p. 14.
" Pnt. Kf 23a M. 134,789.
»» Zt«ch.
Chem. f.Zt*., 27, p. 32.
s« Untereuch. d. Nahr. und Genusem., 6, p. 817.
*o It does not appear clear which cinnamon oil U really meant. The oil from
Cassia lignea le not a commercial article, which the oil from Cinnamonium Cey
lanicum has a quite different Hp. gr. (1.023—1.040).
130. Oil of Cinnamon Leaves. G.-H.-K., p. 381.

S. & Co.41 have examined an oil of cinnamon leaves, having the
the following constants: d = 1.0479; aD = —0°10'; saponification
number 40.2. 10 kilos of oil yielded 1.4 kilos of an oil free from
eugenol, and which distilled between 34° (25 m. m. pressure) and
110° (12 m. m.) The oil contained linalool (citryl-/8-naphthocin-
choninic acid, m. p. 198°) and safrol, but no cinnamic aldehyde.
132. Oil of Cassia. G.-H.-K., p. 383.

Adulteration. S. & Co.42 have repeatedly detected the adul
teration of Chinese cassia oil, with resin and petroleum oil. A sample
having sp. gr. at lo° = 1.070; aD is° = +6°45'; soluble in 2.5 vol.
of 70 l). c. alcohol, from which flakes separated upon standing;
aldehyde content 69 p. c., contained 12 p. c. of resin.
To detect oil of cloves in cassia oil, Pool43 recommends the
following application of Jacquemin's phenol reaction:
1 c. c. of dilute aniline solution is treated with a solution of sodium
hypochlorite, until a faint violet colored liquid is produced. A drop of
cinnamon oil is then added, the mixture agitated, diluted with water and
filtered. Pure cassia oil gives a bright violet filtrate, while, if oil of cloves
is present, the filtrate is dark green.
Because of the unreliability "of color reactions in general, this
test is not to be recommended. 44
In the apparatus used for the estimation of oils by removing a
constitutuent by means of a reagent and measuring the residual oil,
the oil can not be readily treated with a second portion of fresh
reagent or washed before being measured. To obviate these defects,
Chapmann and Burgess45 have devised the apparatus as shown in
the cut:
A flask A of 250 c. c. capacity has a measuring tube B, accurately
ground on. The volume between the zero mark ou the scale C and the
mark d is exactly 25 c. c. The diameter of the tube above the bulb is
about 5 m. m., considerably less than the diameter of the tube below the
bulb. In using the apparatus, 25 c. c. of the oil under examination are
measured off at a known temperature with a pipette into the flask and
then treated with the reagent, the piuchcock f being closed. The aqueous
liquid may then be run off by opening f, and water for washing, or a
*' S. & Co., Kep., Oct. 1802, p. 27.
« S. & Co.. Rep., April, 1900, p. 10.
« Pharm. Werkblad, 40. p. 1101: Chem. Centralbl., 1904, I, p. 404.
** S. & Co., Rep., April-Mav, 1904, p. 23.
« Analyst, 2;">. p. 197.
farther quantity of reagent added through the funnel e. The measuring
tube is fixed in position and the washed oil transferred to it by running
water into e. The oil is brought to the original temperature by means of
running water in the jacket. The meniscus is brought exactly to mark d

and the reading taken on the narrow graduated portion of the tube.
Measuring tubes of different sizes may be used.
Cinnamic aldehyde is official in the Swedish Pharmacopoeia, 8th
ed., having sp. gr. at 15° = 1.054—1.056; aD=±0°; b. p. about
252° with decomposition; soluble in Spiritus in every proportion;
m. p. 7.5° *8
137 a. Oil of Cinnamomum Pedatinervinm.
By distilling th bark of Cinnamomum Pedatinervium, a tree in
digenous to Fiji Islands, Goulding47 obtained 0.92 p. c. of a color
less oil which gradually turned yellowish-brown; di5° = 0.964;
*« M. p. should be —7.5°; S. & Co., Rep. April, 1902, p. 70.
« Thesis, London, 1908; Journ. Chem. Soc., 83, p. 1093.
«„= —4.96'; nD is° = 1.4963; b. p. 180°—255°; saponification

number 4.4 (1.5 p. c. of ester, calculated as linalyl acetate).
The oil contained 50 p. c. of safrol (a-nitrosite m. p. 129°—130°);
30 p. c. of linalool (a-citryl-j8-naphthocinchoninic acid); 1 p. c. of
eugenol (benzoyl compound, m. p. 70°) and probably about 3 p. c.
of eugenol methyl ether.
The terpene fraction boiled from 167°— 172°; di5° = 0.8659;
«D= —17.72°. It yielded a liquid dibromide.
145. Sassafras Oil. (i.-H.-K., p. 394.

Safrol. S. & Co. 48 have carefully determined the constants of
safrol from separately recrystallized safrol by freezing. The limpid
liquid had di5° = 1.1058—1.106 (usually given as 1,108); n„i7.5° =
1.53917. The congealing point was +11.2°.
Chapman40 recommends the following color tests for safrol, iso-
safrol and other phenols. 1 c. c. of the phenol is dissolved in 5 c. c.
of acetic anhydride and then (u) a fragment of zinc chloride or (b)
one drop of cone, sulphuric acid added. The colors obtained with
different phenols are given in the following table :
Phenol. With sulphuric acid. With zlnc chioride.

brown — purple — wine red pale yellow
rose pink — light brown rose pink
Safrol emerald green — light brown pale blue — light brown
faint pink — red pink — brown
purple — indigo blue blue violet — brown
none — yellow pale yellow — brick red
149. Oil of Laurel Leaves. G.-H.-K., p. 402.

From Laurel leaves from plants growing wild in the Jordan
valley, S. & Co.50 obtained an oil which had sp. gr. at 15°=0.9237;
«u= —15° 34'. Soluble in 1 volume of 80 p. c. alcohol.
155 a. Apopin Oil.
In Formosa an essential oil is produced, whose odor greatly
resembles that of camphor, and which the natives call Shu-yu (evil
*» 9. & Co., Kep,, Uep., 1903, p. 98.
« Analyst 25, p. 813.
so 8. & Co., Kep., April, 1902, p. 78.
PHARMA CEVTICA L REVIEW. 277
smelling oil). It has been called A1iopin oil from the producing
district Aupin. The exact botanical source is not kno\yn. The
natives use it to adulterate camphor oil.
According to Keimazu51 the oil is n colorless liquid which turns
brown on exposure to the air. d,.-,° = 0.9279 ; a„= +17°0<>' to
17° 19'. 42 p. c. of the oil boiled from 195°—203° C.
The oil contained camphor, m. p. 176° (oxime, m. p. 117°—118°) :
eugenol (benzoyl compound, m. p. <>9°); snfrol (homopiperonylie
acid, m. p. 127°—128°); cineol (hydrobromide, m. p. 53—54°);
dipentene (tetrabromide, m. p. 124°—125°).
158. Oil of Spoonwort. G.-H.-K., p. 407.
By the distillation of fresh scurvy-grass, without the addition
of white mustard, S. & Co. 32 obtained 0.04 p. c. of oil. The addition
of mustard reduced the yield slightly. 138 kilos of fresh herb pro
duced 13.7 kilos of dried herb, which when mixed with 6 kilos of
ground mustard and distilled yielded 24 grams of oil, corresponding
to 0.0173 p. c. of the fresh grass, and 0.175 p. c. of the dried grass.
The oil had sp. gr. = 0.933—0.950: «„= +52° 38'- +54° 38'.
Gadamer53 has detected a slight dextro rotation, +4.75° in the
secondary butylamine derived from the secondary butylthiocarbimide
of oil of cochlearia.
According to Urban54 the volatile oil from the seed of Cochlearia
officinalis, L., is identical with the oil from the herb. The oil was
obtained in a yield of 0.485—0.492 p. c. with or without the addi
tion of white mustard seed.
161. Oil of Mustard. G.-H.-K., p. 409.

Estimation. Mann55 recommends the following method to
determine the p. c. of oil in mustard seeds:
10 grams of powdered mustard seeds are moistened with 20 grams of
water, allowed to stand (1 hours and distilled with 200 grams of water.
The distillate is collected in a 10 p. c. ammonia solution. An excess of
silver nitrate solution iH added, and the precipitated silver sulphide is filtered
off, washed and converted into metallic silver by heating. The weight, of
silver multiplied by 0.4938 gives the weight of oil.
oi .Imirn. Pharm. Soc. Japan.. March, 1903; S. & Co.. Rep , Oct., 1908, p. 10.
« S. & Co., Rep., April. 1900, p. IK.
53 Arch. d. Phimu , 239. p. 283.
" Arch. <1. Pharm.. 241, p HOI.
« Arch. d. Pharm., 240, p. 161.
Roeser58 proposes the following modification of Gadamer's

method of assay:
5 c. c. of a 1 p. c. solution of the oil in 95 p. c. alcohol are placed in
a 100 c. c. grad. flask and 10 c. c. of ammonia and a little distilled water
added. 10 c. c. of N/10 silver nitrate solution are gradually added with
constant stirring and the mixture allowed to stand 24 hours. The flask
is then filled to the mark with distilled water and 50 c. c. of the liquid
filtered off. An excess of N/10 potassium cyanide is added and titrated
back with N/10 silver nitrate solution in the presence of a few drops of a
weak ammoniacal solution (5 p. <:.) of potassium iodide.
Dieterich07 determines the p. c. of oil in the seeds or the purity
of the oil itself as follows: '
5 gma. of the seeds are crushed in a mortar, transferred to a 200 c. c.
flask with the aid of 100 c. c. of water, and the flask well closed is then
set aside at a temperature of 20°—25° for two hours. 10 grams of alcohol
are then added and the flask is connected with a condenser which is con
nected with a receiving flask of 200 c. c. capacity containing 30 c. c. of
ammonia water into which the condenser tube dips. To prevent loss, the
first receiving flask is connected to a second, containing ammonia.
The mixture is distilled until 50—60 c. c. of distillate collect in flask
No. 1. The apparatus is disconnected and the condenser washed out with
water, into the receiver. A solution of silver nitrate in excess ib added to
the distillate and the mixture heated on a water-bath to promote the pre
cipitation of silver sulphide. The precipitate is collected on a filter paper,
which has been previously washed with successively, ammonia, hot
water, alcohol and ether. The precipitate is washed with hot water, alco.
hoi, and finally ether, dried at 80° V. and weighed.
The weight of silver sulphide multiplied by 0.4311 gives weight of oil
in seed.
Mann"'8 has devisved a method for accurately determining the
percent of oil in mustard or others species.
About 20 grams of finely ground spice are mixed with powdered pumice
stone and distilled in an apparatus as shown in Fig. 1, until 400—900 c. c.
of distillate are obtained. The distillate is collected in a flask or measuring
cylinder holding 1 —1.5 liters, furnished with a long neck which is graduated
to hold 50 c. c. Add sufficient pure salt to the distillate to make about a
25 p. c. solution and shake out the essential oil with rhigolene (light
petroleum benzin), b. p. 20°—35° C. After agitation and separation, add
sufficient water to bring the layer of benzin into the neck of the flask and
add more rhigolene or benzin to make up 50 c. c.
s« Joum. de Pharm., (6). 1.1, p. 361.
57 Pharm.d. Ztg., 45. -2*0,
p. 767.
•a Arch. Pharm., p. 149.
( To be continued. )
Plant Pigments.*
By /. W. Brandel.
According to Molisch a0 the Phaeophyceae, Diatomaceae and

some Orchideae contain a brown coloring matter which is closely
related to chlorophyll and is called phaeophyll. It is readily changed
to chlorophyll. It is for this reason that the brown algae rapidly
become green in hot air, hot water, alcohol, etc. This phaeophyll
plays the same function toward these brown plants, as the chloro
phyll does to the green plants.
The Phaeophyceae and Diatomaceae also contain leucocyan
which with acids give the blue or blue green phaeocyan.
From the examination of a large number of flowers by means
of the Leitz micro-spectroscope, Kraemer40 draws the following
conclusions in regard to color in plants:
There are two classes of color substances:
(a) Organized color principles characterized by being an organic
part of the plastid body ; insoluble in water or dilute alcohol ;
soluble in xylol, etc. This class consists of three main pigments:
chlorophyl ; chromophyl found especially in the flowers, certain
roots, and ripening fruits of higher plants; etiophyl found especially
in the leaf-bud of Spathyema foetida.
(b) Unorganized color principles, which are not a fundamental
or organic part of the plastids, and occur either in the vacuoles of
the cells of higher plants as well as fungi or in the vacuolules of the
plastids of the brown and red sea-weeds. They are soluble in water
and dilute alcohol and insoluble in xylol, etc. Unorganized color
substances are produced in large amount in early spring foliage,
foliage of alpine plants as well as autumnal foliage; the brown and
red marine algae; and the foliage of certain species of rose, beech
nasturtium, etc.
3» Bot. Ztg., m, u. 181.
*o Proc. Am. Phfl. Soc., 48, No. 177; Bull. Torrey Bot. Club, 38, p. 77.
280 PllAIlilACECTICAL REVIEW.
Willstiitter41 who undertook n careful study of the composition of

chlorophyll with special reference to the separation and characterisa
tion of chlorophyll derivatives by treatment with acids and alkalies,
has isolated a great number of substances colored and colorless,
which, however, have not been shown to have any special bearing or
relation to flower pigments. It is. however, interesting to note, that
the term chlorophyll, as commonly used, is a mixture of substances,
the principle one of which is a complex magnesium derivative. Two
yellow pigments, which accompany chlorophyll, are earrotene and
xanthophyll. The earrotene is probably identical with the earrotene
from carrots, and also with Bougarel's erythrophylH- and Schunck's
chrysophyll.
While without special reference to plant pigments, it is interest
ing to note a general explanation of the cause of color in organic
compounds by Hale.4a From a study of a large number of com
pounds, he draws the conclusion that isorropesis is the cause of color
in aromatic as well as the aliphatic series. By isorropesis is meant
the making and breaking of contact between atoms which give
marked activity to these atoms. This change of linking, therefore,
which must accompany the transformation of one modification of
the compound into the other
-CH2—C— —CH-C— CHs-O—C—CHa CHs—C-O-CH3
I■ 7=1 I i| |: 7=1 I I
0 OH 0 0 0 0
is the source of the oscillations producing absorption bands. If
these oscillations are synchronous with light waves of a high fre-
quency, they give rise to absorption bands in the ultra violet or in
visible end of the spectrum and the compound is colorless. If the
oscillations arc of a less frequency, the absorption band appears in
the visible region of the spectrum and this absorption of colored
rays, results in the compound taking on the complementary color.
ii Ann. :i.">0, pp. 1, 48; 8">4, p. 2UT> ; ;!.".5, p. 1.
*2 See p. Sii.
« Pop. Sec. Monthiy. 72, p. 11(1.
PHARMACEUTICA h REVIEW. 281
Literary.
Books Reviewed.
Die Chemische AffinitXt cnd ihke Messunii. Von Dr. Otto
Sackur. Heft 24. Die Wissenschaft, Sammlung naturwissen-
scbaftlicher ami mathematischer Monographien. Braunschweig,
F. Vieweg & Son, 1908. Pp. 12b. Preis: (ieheftet M. 4.00,
gebunden M. 4.80.
The l)urpose of this contribution is to summarize the problems
which the study of chemical affinity presents and to point out the
meaus of their solution. A complete bibliographical presentation
has not been attempted. Inasmuch as chemical affinity is commonly
measured by the maximum amount of work which can be obtained
from the reaction under consideration, the thermodynamic basis for
such computations has been" carefully considered by the author.
After a brief historical introduction given in the first chapter,
the subject matter is treated in five additional chapters whose titles
are as follows: The concept of maximum work and the second law
of thermodynamics; Evaluation of the affinity from the extent of
the chemical change; The electrical method of measuring affinity;
Affinity and temperature; Results of measurements of affinity.
It is rather to be regretted that more space is not devoted to
experimental methods of measuring affinity. Nevertheless, the student
of chemistry will doubtless find the volume a very helpful one to
peruse. It is clearly written and the paper and print are excellent.
The volume compares well with the earlier numbers of the series.
Ij. K..ihlenbcrg.
Determination of Radicles in Carbon Compounds, by H. Meyer
and J. Bishop Tingle. Third edition, revised. First thou
sand, pp. XIV, 218. John Wiley & Sons, New York, 1908.
Price fl.2i>.
The third edition of this well known and useful work was neces
sitated by the great number of new methods devised since thy second
edition.
The various new methods, instead of being placed in the proper

chapters with the older methods, have been placed all together in
an appendix, arranged however in the same order. In each case
cross reference is made by page to a similar method in the first part
of the book. This arrangement of the new material affords a con
venient means of readily referring to the new methods, without hav
ing to search for them among the larger number of older methods.
One can readily see the advantage of bringing a book up to date,
which is merely a collection of methods and not a connected text, by
the supplement method rather than by rewriting the whole. The
main body of the book has been revised for the elimination of typp-
graphical errors and. of statements which investigations have shown
to be incorrect. A few references to recent publications have also
been inserted.
The work contains chapters on the following general subjects : Deter
mination of hydroxy groups; determination of methoxy, ethoxy and
carboxyl groups; determination of carbonyl and methylene groups;
determination of amido group; determination of diazo group. The
various methods in each chapter are arranged in a purely arbitrary
order without any attempt at a logical classification, if indeed such
is possible. The value of the book is well stated in the introduction
as follows. "There are very few processes which like Ziesel's method
for determining methoxy, can be applied almost universally. Usually
then, it becomes necessary for the analyst himself to select the
method most appropriate for his special purpose or perhaps by a
combination of several to devise one which may lead to the desired
result. The successful methods hitherto proposed for the determina
tion of organic radicles have therefore been collected together in this
work." /. W. Brandel.
The Cultivation and Handling of Golden Seal, by Alice Henkel,

Assistant, and G. F. Klugh, Scientific Assistant Drug Plant
Investigations. Circ. No. 0, Bureau of Plant Industry,
U. S. Department of Agriculture.
The scarcity of wild growing golden seal and consequent increase
in value of the drug have led to experiments in its cultivation, which
have been carried on for a number of years by the Bureau of Plant
Industry.
The above circular contains information on identification, geo

graphical distribution and conditions necessary for growth of the
plant, also the preparation of the drug for the market and relations
of supply and demand.
The current price of the root is $2.00 a pound, and it appears
that one should be able to raise the drug at a profit. The demand
for it is somewhat limited and if many are successful m raising it,
there would result a corresponding decline in price. R. H. D.
An aid to materia medica by Dr. Robert H. M. Daw barn. Fourth

edition revised and enlarged by Dr. Eden V. Delphey. One
vol., pp. XI, 338. The Macmillan Company, New York,
1908. $1.75 net.
"For students, the author believes such a volume as this to be of
special value, .since examiners require much that the practitioner soon
lays aside" (Italics our own). Unfortunately this is only too true
of a host of isolated data which candidates for state board examina
tions have to memorize. To the credit of the author it should be
said that his compilation has not the earmarks of the ordinary
quiz compend. The data crowded together in this tome of pocket
size are indicated in the table of contents herewith reproduced.
Drugs: Official preparations, their strength and dosage (pp. 1—145);
Prescription writing; An easy method of writing prescriptions in the metric
system; Incompatibilities; Some dangerous abbreviations; List of articles
added to the Pharmacopoeia; List of articles dismissed from the Pharma
copoeia; List of changes of official Latin titles; List of changes of official
English titles; Table showing the strength of the more important pharma-
eopoeial preparations in the present and in the proceeding Pharmacopoeia;
Table of solubility of chemicals in water and in alcohol; List of newer un
official drugs and remedial agents (p. p. 198-338).
So long as examinations are conducted according to present
methods, books of this kind will be demanded. This particular com
pilation is one of the least objectionable of its kind which has yet
come under the eyes of the reviewer.
That the "list of 660 of the more important newer remedies
is one which he (the student) will hardly find elsewhere" the writer
is somewhat inclined to doubt, though the information is so arranged
as to make a very neat looking page. E. K.
284 1>HA RMA CEUTWA I. REVIEW.
Sy.\thetis('h-Oi!gaxis<'he Chemie deb Neuzeit. Von Dr. Julius

Schmidt, A. 0., Professor an der konigl. technischen Hoch-
schule, Stuttgart. Ein Bd., pp. x, 18">. Verlag von Friedrich
Vieweg unci Sohn in Braunschweig. 190H. Geh. M. o..">0;
geb. M. 6.20. .. ,
To the laity the term synthesis implies u mysterious realm with
untold possibilities. To the man of practical affairs who. once upon
a time, included chemistry in his curriculum, it suggests rigid mental
discipline very well for college days but scrupulously to be shunned
after commencement.
Everybody who has dabbled in chemistry recalls Woehler's syn
thesis of urea, at least when some one makes mention of this classic
incident. Those who have had a semester or a year of organic
chemistry recall probably with a shudder the size of t he four volumes
of Beilstein and the four supplementary volumes to the last edition
and hold organic synthesis responsible for the tens of thousands of
carbon compounds. If even a Professor Ostwald talks of the woods
of organic chemistry in which the beginner is so easily lost, we cer
tainly cannot blame the beginner himself when he recalls his solitary
wanderings through this jungle with the aid of midnight oil.
But, have we not been told that organic chemistry has had its
day and that physical chemistry is at present of prime importance?
And yet. here we have an author who writes a book, not on the
history of organic synthesis but on the progress made by the syn
thetic method during the past ten to fifteen years. Weareeven told
that a single method, viz. that commonly known by Griguard's
name has been responsible for about four hundred and fifty original
contributions in scarcely eight years.
It must be quite evident that after all organic chemistry can
have lost little of its productiveness and that the future cataloguer
of carbon compounds will find a few new substances to add to the
tomes of Beilstein.
Nor are these methods of synthesis of theoretical value only.
The value of the products of the German dye-stuff industry amounts
to about 250 million marks, two-thirds of which products are ex
ported. It is not surprising, therefore, that these men of practical
affairs had the portrait of Kekulc, the visionair, painted and hung
in the National Gallery at Berlin. Neither is the outputdiminishing
i
us some fondly believe, for in 1900 it amounted to 27 million marks
more than in the year previous.
That the pharmacist is affected by this continued development
of organic synthesis, becomes very apparent when he glances at his
cabinet of new remedies and receives new literature on a so-called
synthetic with well nigh every mail. But, while all rapid progress
has its annoying features, the pharmacist cannot but contemplate
with interest the changes that have taken place in modern materia
medica since the medical exploitation of chloral hydrate or even of
antipyrine.
He certainly was cognizant of the constant rise in price of
camphor and if he did not look behind and beyond this mere com
mercial change he was a dead pharmacist indeed. The monopolising
of the camphor industry by the Japanese government and the striv
ing of the chemist to produce camphor artificially on a commercial
scale are two events in modern history that have been of the greatest
concern to others than the druggist. While optically inactive cam
phor has been made successfully on a commercial scale and while the
Committee of Revision of the U. S. P. has been trying to ascertain
whether optical differences were accompanied by therapeutic differences
of import, and the chemist of the food and dairy commission has
been depending on the polariscope for the detection of artificial
camphor in U. S. P. preparations, there now comes the news that
this Grignard method enables the artificial production of camphor
that is optically active.
Such are the results produced by the study of synthetic reactions
in the quiet laboratory of the organic chemist. Not only in the more
friendly rivalries of the peaceful industries do they play an important
role, in the conquest of nature by man, but also in the bitter wars
between nations in which smokeless powder carries to enormous
distances the death producing bullets of an unseen enemy.
If only the pharmacist would allow his fancy an occasional flight
he might find more pleasure, even if not more profit, in a business
that is a severe tax on his time and patience. Each new remedy,
each new perfume that finds a place on his shelves, ought to add an
other chapter to a continuous chemical romance. E. K.
Les ferments metalliques et leur emploi en the>apeutique, par

M. le Professeur Albert Robin. Un volume in-18, pp. 252,
avec nouibreux graphiques. 1907. 4 fr.
A dose of from one to several ten thousandth parts of a grain,
no doubt, will seem exceedingly •homeopathic to pharmacist as well
as to physician. Yet such are the amounts administered when some of
the noble metals are given in a very fine state of division. However,
the agents in question are not an argentum alcoholisutum or an
aurum alcoholisatissimum, if the writer be pardoned for squaring
a superlative, but they are metals reduced to an extremely fine state
of division either by electrolytic means (hydrosols) or by chemical
means (organosols).
The reports on the therapeutic action of these preparations were
apparently received at first with the same incredulity with which the
socalled oligodynamic force of the gold coin as manifested toward
algae was regarded.
To think of these metals as ferments also comes no doubt as a
shock to the old time organic chemist, but the shock can be no
greater than that received when we are told that e. g. platinum
sponge, when acting as a socalled catalytic agent in the manu
facture of sulphuric acid, ''is poisoned" by minute traces of arsenic in
the sulphur dioxide.
However, scientific progress of the past decade or two has com
pelled us to change so many of our older notions that even the
physician of the regular school no longer laughs at homeopathic
doses, even though he be not ready to swallow the homeopathic
theory of similia similibus curantus.
As a contribution to a special chapter on new remedies, the
monagraph by Robin will, no doubt, be welcome to many a person
whose attention has been drawn to the striking physiological effects
produced by inflnitessimal amounts of the precious metals in a very
fine state of division. E. K.
Les pots de i'Harmacie. Leur inscriptions presentees sous forme

de dictionnaire. Par le Dr. Paul Dorveaux. Un tome, pp.
89, avec 14 planches. A. Maloine, Paris, 1908.
This, the latest product from the pen of the well-known Librarian
of the Superior School of Pharmacy of the University of Paris, will
be welcomed by all who are interested in the application of the fine
arts to our calling as well as to the pharmaceutical lexicographer.
But few lovers of the ceramic arts realize to what extent ceramics
was stimulated by the sixteenth and seven
teenth century apothecary and his love for the
artistic adornment of his "officine'". In so far
as faience is concerned, this influence is made
apparent in this monograph and the fourteen
plates that accompany tiie text.
Dorvea u x
groups pharma
ceutical pots in
to six classes:
1) chevrettes,
"Pot a Canon*' used for syrups,
from Reber Collection. honeys and oils;
2) bouteilles,
for distilled waters; 3) c rue hes, for
syrups and distilled waters; -i) pots a
canon, for ointments, opiates, confec
tions, electuaries, halms, etc.; 5) pi-
lulieres, for pills: 6) vases u. the- "Chevrette"
riaque for this and other "grandes from Reber Collection.
compositionsgalenique." Of these
there were four, viz. "la theriaque,
le mithridate, la confection d'al-
kermes, et la confection d'hya-
cinthe."
Fully one-half of the brochure
is devoted to a dictionary of the
inscriptions collected from phar
maceutical pots either directly
by the author himself or by
correspondents. While the author
himself points out that this
dictionary is far from complete,
it is certainly a valuable be
ginning in this particular field
of lexicography.
By way of introduction to this
second part the author enter-
c,-,,,->, ..•„.„ Kt.bi.i.c.il ■ : tains his readers with illustra-
tions of errors made in the inscriptions. Thus e. g. Lareine

Despre should he E.(au) de la reine des pres, which comical
mistake occurs on a bottle of the Central Pharmacy of the Hospitals
of Paris, a photograph of which is reproduced in "La Pharmacie"
for 1906, p. 377. That it requires something more than a knowledge
of pharmaceutical nomenclature and a thorough acquaintance with
the materia medica of all times, viz. an intuition of no mean order,
becomes apparent from the uses to which e. g. the abbreviation "E"'
is put on the different styles of pharmaceutical pots. While on a
bottle it stands forEau (water), on a "pot a canon" it may stand
for either electuary, elixir, empl&tre (plaster) or extract.
What might be designated the third part, consists of fourteen
excellent half-tone plates representing twenty-eight different pharma
ceutical pots.
Throughout, the main text of the brochure is supplemented by
numerous notes revealing that knowledge of historical detail for
which its author is so well and so favorably known. While the
writer makes no pretense whatever of a knowledge of pharmaceutical
pottery, he finds that a large collection has evidently escaped the
author. This is the collection in the Victoria and Albert Museum
at South Kensington, unquestionally one of the finest in existence.
Of this collection photographs of not less than seventy-seven speci
mens are available, some photographs representing two or even
three pots.
For some time the writer has not enjoyed an historical mono
graphs so much as this one. May its author long continue his
activities in the uplifting of our calling by bringing to our attention
the interesting past of the urs pharmaceutics . E. K.
Volume 26. OCTOBER, 1908. Number 10.
American Pharmaceutical Association.
"Let us »top clamoring for recognition a*

proteesional men, or elevate American pharmacy
to the dignity of a profes»ion hj demasding
appropriate icholarahip ami attainmenta."
The Hot Springs meeting was unquestionably a success and
there is little doubt in the minds of many, if not most, members
that a meeting in the even more distant Los Angeles next year
would be an even greater success. As was pointed out, the American
Pharmaceutical Association has become sufficiently well established
to be independent of time or place of meeting, also of affiliation with
other bodies. Vet this is no reason why we should neglect to con
sider advantages that may accrue to American pharmacy, and thus
directly or indirectly to the American Pharmaceutical Association,
by giving due consideration to time and place of meeting, also to
other organizations.
That even in hot weather good meetings can be held was again
demonstrated, but, other things being equal or nearly so, everyone
prefers a cooler clime. There appears to be no sufficient reason why
we should go to southern California in July or August. If the
pharmacists of the southwest have been stimulated to renewed
activity by our meeting in their midst, the Association was fully
justified in going so far from the geographical center of its member
ship. The pharmacists of the western coast certainly have a right
to expect us to come west of the Rockies once in twenty years.
However, we must consider other factors than those of geography
and climate, viz. our relations to and affiliation with other
branches of our calling. While the American Pharmaceutical Associ
ation has at all times been more than willing to extend the right
hand of fellowship to the N. A. R. D., the latter does not seem to
have indicated any great willingness to receive it. At the Hot
Springs meeting the American Pharmaceutical Association went so
far as to postpone setting time and place for the next meeting until
(289)
the N. A. R. D. might be heard from. The greetings extended to the

N. A. R. D. certainly do not lack in cordiality.
1. That, we extend fraternal greetings to the National Association of
Retail Druggist* shortly to convene at Atlantic City, N. J., and wish that
organization abundant success in every effort which it may make to elevate
the dignity and honor of American pharmacy and to 8' cure for those who
follow that calling a degree of commercial prosperity and financial reward
that shall be proportionate to their educational acquirements and to their
moral and legal responsibilities.
2. That there be appointed a special Committee on Relations with the
National Association of Retail Druggists, said committee to consist of three
members, and to take into consideration the means whereby each associa
tion may strengthen the hands of the other in its special lilies of activity,
and to render more fruitful the measures of reform and progress which are
common to the purposes of both organizations.
3. That it is suggested to said committee that it consider the advisa
bility of selecting a common meeting place for the annual conventions of
both associations and the selection of such date for the same as will per
mit, at least, the sessions of the Commercial Section of this Association to
be contemporaneous with the first general session of the National Associa
tion of Retail Druggists.
■t. That all determinations and recommendations of said committee
shall be reported to the Council for consideration and disposal.
5. That a copy of these resolutions shall bo forthwith transmitted to
the Executive Officers of the National Association of Retail Druggists.
Besides, there are other associations which we cannot afford to
ignore forever. The American Chemical Society is contemplating the
establishment of a Section on Pharmaceutical Chemistry. If such
section be established, it will be in the interests of the American
Pharmaceutical Association to secure a good attendance. But such
meetings at great distances are costly affairs. In 190.'5 the A. A. A.
S. and affiliated societies, including the A. C. S. met in Columbus,
Ohio, two weeks before the American Pharmaceutical Association
met at Put-in-Bay in the same state. Such an occurance is indicative
of gross carelessness. While we need not tie ourselves to any other
body or group of associations, the time certainly has come when we
can no longer afford to ignore this important factor of interrelation
of pharmacy and the basal sciences as represented in the A. A. A. S.
and affiliated societies.
Possibly of equal importance is the problem of reorganization,
a question that has demanded no little time and attention in recent
years. A centralized form of government has its advantages which
become more apparent with the increased growth of already large

and unwieldly national bodies. Inasmuch, however, as there are two
sides to every question, we should not overlook the disadvantages
that must necessarily accompany such a change. As for himself,
the writer, some years ago decided in favor of reorganization.
As seen with his mind's eye, this reorganization involved a
number of changes. First, the closer touch of the association at
large with the individual member. Inasmuch as it is utterly impos
sible for the average member to attend the annual meetings of the
Association with any degree of regularity, this was to be brought
about by journalizing the proceedings.* After considerable hesitation,
the "Bulletin" was established. While, as our retiring Treasurer
points out, the "Bulletin" is doing much to hold our membership
and possibly aids in adding to it, this mode of publication is scarcely
worthy of such a body as the American Pharmaceutical Association.
The second step to be taken consisted in the establishment of
local sections. t Not only does the individual member want to come
into touch regularly with the organization as a unit by receiving a
journal issued monthly or oftener, he wants to meet his fellow-
members oftener than once in five or ten years, indeed oftener than
once a year as do the few who attend the annual meetings regularly.
The success of the local sections already established has fully proven
the soundness of this reasoning.
The third step consists in systematizing the business transacted
at the annual meeting. This process has been going on ever since
the sections were established in the eighties. Still the old democratic
spirit, as we may call it for want of a better characterization, i. e.
the desire that each and every member should have a part in every
transaction, has until today proven too strong to secure the best
results from this specialization — not a perfect division as yet — of
labors. Thus the advantage of having simultaneous sessions of
sections has been retarded even by some of those who are now
clamoring loudly for "reorganization". •
At the last general session those who voted against the report
to suspend the by-laws for a year were charged with blocking pro
gress. Two years ago the following motion was introduced into the
* See tble journal, vol. 20. p. 441.
t This journal, vol. 22, pp. 228 & 321.
-'92 PHARMACEUTICAL REVIEW.
Council as a further step in the process of evolutionary reorgani

zation that has been going on for at least two decades.
"Moved by Edward Kremers and seconded by C. E. Caspari that the
Programme Committee be instructed to arrange the first sessions of the
several sections at times which do not conflict, and to leave the arrange
ment of subsequent simultaneous sessions to a committee of chairmen
of the sections." *
It was adopted by the Council, and ratified by the Association
at large, but when the programme for the next annual meeting was
arranged, these instructions from the Association were ignored.
Without a spectacular change in our constitution and by-laws we
might have had a more effective programme for the past two years.
This systematizing of the business of the Association also calls
for enlarged powers of the Council. The general business of the
Association will more and more have to be transferred to this
central body. With this object in view it has already been enlarged
by the addition of members not elected by the Association at large,
in general session assembled, but elected by the local sections, thus
providing for a better representative government, at least in a re
stricted degree. More than that, several of the most important
committees appointed or elected this year are committees of the
Council and are not expected to report to the Association at large
at all. Thus our general business is being centralized more and
more. If this continues, it will require but a few years more, till
the Council will transact practically all of the general business, and
the Association, in general session assembled, will act merely as a
ratifying body.
Whether we shall want to take the next step and turn over to
the Council the general business without ratification, will depend
largely upon the Council and those who have made "reorganization"
their battle cry.
In voting one thousand dollars for the traveling and hotel ex
penses of a committee, the Council of last year took a step that is
an exceedingly dangerous one. No one may wish to question the im
portance of the work of the committee thus favored, but it is not
a question merely of individual merit, but one of general policy as
* Proc. A. Ph. A., 54, p. 47.

well. Aside from the question of general policy, that of expense

must be considered. The writer has been informed that the old
Council has voted as much as three thousand dollars out of the well
lined purse of the Association and that those who were most
anxious to spend this money were not the ones who did most to
accumulate it.
If the old Council has thrown itself open to the charge of what
some members have designated as extravagance, the new Council
though scarcely organized, has been looked upon with misgivings.
In addition, the open session of the Committee on Reorganization
has been spoken of in terms of severe condemnation and even the
sincerity of its prime movers has been questioned. These reports
are referred to in this connection, not as charges but merely as an
explanation why a pnrt of the majority of those present at the
last general session voted against ''reorganization. " As pointed
out, the process of evolution of reorganization has been going on
these many years and is not at a standstill even now.
As soon as the Council, not only in its entirety, but, what is
equally important, each and every member thereof, possesses the
confidence of the Association a further step will undoubtedly be
taken. The mere changing of words, be they of constitution or of
by-laws will make but little difference.
Thanks to an increased membership, the finances of the Asso
ciation are in a good condition. The striking aspect about the in
creased membership and the consequent improvement of the treasure.
is this that it appears to be almost wholly independent of the place
of meeting. By far the larger percentage of new members seems to
be added between meetings through activities of relatively few
individuals.
After a number of years that were gloomy, Ex-Treasurer Shep-
phard must have taken extreme satisfaction in the writing of his
last report of which we, herewith, present his own abstract. The
services which Mr. Shepphard rendered during his twenty-two years
of office were not merely those of a faithful accountant, he was a father
to the Association as well. The legacy which he leaves is not only
that of a good balance, or his contributions to the Endowment
Fund, it is that of a tradition of a good and faithful servant whom
all respect, honor, and love.
Abstract of A. Ph. A. Treasurer's Report, July 1, 1907, to

July 1, 1908.
RECEIPTS.
fash on hand .luly 1, 1907 ! * 8,855.75
Kecelved from sale of certificates 73.50
" " " '" proceeding 96.43
" " " " badges and burs 50.25
" " '' " National Formulary '. 6,01 0.88
.' " " " semi-centennial index -8.08
" " interest on deposit, -New England TruBt Co., Boston, Mass. 211.08
"
■ " " annual dues
" • Ebert Fund 8.525.00
30.00
" " life membership feeB 250.00
for Endowment Fund 2,189.00
f20,325.97
EXPENDITURES.
Proceedings * 4,022.18
Stenographers 269.25
Journals for Keporter on Progress of Pharmacy 31.14
SularieB 2,800.00
Traveling expenses ... 96.69
Section on Practical Pharmacy anil Dispensing 23.57
" " Education and Legislation 21.41
" " Commercial Interests 3.17
" Scientific Papers 3.17
" Historical Pharmacy 38.19
Committee on membership 65.00
" prize certificates 10.00
Printing and Htntionery 310.46
Insurance 31.00
Badges and bars 76.66
Certificates 58.50
Miscellaneous expenses 227.62
-National Formulary 1,880.06
Semicentennial Index .36
A. Ph A. Bulletin 1,309.30
Ebert memorial volume 508.04
Balance of salaries for the fiscal years 1904-1905-11)06 840.00
Ebert prise " 30.00
Life Membership Fund 250.00
Endowment Fund 2,189.00
Cash to new account 11.231.20
~*20,325T97
This has been a prosperous year financially. In the list of disburse
ments there are two items that may be called "extras;" the eost of the
Ebert Memorial Volume, $508.04. and the balance of salaries for 1904-
1905-1906, $840.00.
The amount paid out for Proceedings this year was $1238.12 more
than the previous year, because a heavy bill for expressage and postage
was carried over from last year and the 1907 volume was 120 pages larger
than the volume for 1906.
In addition to this we have paid the officers their full salaries this year
and not reduced them lt%, as in three previous years.
We have not used the income from the Life Membership Fund, $494.09,
for current expenses, as in many previous years. The excess of receipts
from the sale of National Formulary over disbursements was $228.82 less
than the previous year. The cost of the Bulletin should also be considered.
It amounted, this year, to $1309.30.
Notwithstanding all these facts, our net cash balance July 1, 1908,
exceeds that of July 1, 1907 by $1,835.45, and the increase in value of the
Funds, during t he year, was $3005.42, making a total of $4900.87.
I am pleased to call particular' attention to the increase ot $2237.11

in the Endowment Fund. Lwt uB ull help along the good work of this
Fund: by giving something to it, be the amount ever so etnul), or, if we
cannot do that, let us talk it up. Talking anything up, especially if the
cause has merit, is often a wonderful help to it. ,
The Ebert Prize was given this year, therefore the amount of that.
Fund is practically unchanged. The time has not yet come lor us to receive
from the estute of our beloved friend, Albert E. Ebert, the generous bequest
he mude to us in his last will nud testament.
The several funds, .July 1. 1908, ore as follows:
Kbert Fund .' .' '..$ 941.96
Centennial Fund L'.24s.65
Life Membership Fund 16.0H4.55
Endowment Fund : 2,445.81
Total value of above-named Funds, July 1, 1908 ....$21,670.47
There has been no draft on the Motter Fund. The amount July 1,
1!)08, was $27.68.
Four members have been re-instated during the year by payment of all
back dues, according to Article I , Chapter VIII. of the By-Laws.
I would repeat, with emphasis, the thought expressed in previous re
ports, viz.:—that the influence of the Bulletin on our work is good, very
good.
This is my twenty-second and last annual report as Treasurer and it is
a great pleasure to be able to report our finances in so normal and healthy
condition.
I thank you all, each and every member, for your uniform courtesy,
kindness and help during the past years. May the Association go on
steadily to a glorious and useful future and I most sincerely believe that
it will.
S. A. P. Shpppard, Treasurer.
In accordance with the suggestions made a month ago* a com
mittee on non-official standards has been appointed. This com
mittee is large enough and broad enough to cover all legitimate
pharmaceutical interests. Through its membership it will be in
touch with the U. S. P. Revision Committee, the National Formulary
Committee, the Council on Pharmacy and Chemistry of the A. M. A.
and even the Standards Committee of the Association of Agricultural
Chemists which has been enlarged by the addition of representatives
from the Association of State and National Food and Dairy Depart
ments. As to the further purport of the Committee, the resolutions
calling for its election will be of interest.
Rebolved: 1. There shall be a standing committee of the council to be
known as the Committee on Standards of non-official drugs and chemical
i Hee thtH Iournal. No. 9. p. 257.
29« PHARMACEUTICAL REVIEW.
products, consisting of fifteen members, elected by the council, but the

members of such committee need not be members of the council.
2. The first committee shall be constituted as follows: two represen
tatives from firms engaged in the manufacture of pharmaceuticals, two re-
representatives from firms engaged in the wholesaling of drugs and chemi
cals, five retail druggists, and four representatives from the faculties or
colleges of pharmacy.
3. The committed shall prepare from existing sources of information, a
tentative list, subject to revision, correction and extension by this associa
tion, of the principal drugs, and medicinal preparations not recognized by
the United States Pharmacopoeia or National Formulary, which are of
importance in the chemical and pharmaceutical arts, with a suitable system
of nomenclature for the same, and shall adopt suitable limits of strength
and purity therefor.
4. The chairman of said committee shall be designated by the Council,
and the Committee shall report progress annually.
5. The Committee first chosen shall serve for one year, and at the next
annual meeting of the Council shall report upon a plan for the permanent
organization of the Committee, and also upon a plan for the permanent
continuance of the work.
In this connection it. may,not be out of place to point to the
fact that the Association has gone on record with regard to the
desirability, or rather neeessity, that each place where medicaments
are dispensed or drugs are sold should be provided with the proper
works authorized by law us the standards of t he country.
"Moved by J. H. Beal, and seconded by M. 1. Wilbert, that it be the
sense of the Council that every pharmacy, drug store, public hospital, or
other public institution where drugs and medicines are prepared or dis
pensed, should be provided with a copy of the latest edition of the United
States Pharmacopoeia mid National Formulary, and that all state phar
macy laws should contain a requirement to that effect.*'
Summing up the situation, we have reason to believe that with
the Hot Springs meeting, the A. Ph. A. haH taken another forward
step in the advancement of American pharmacy. It is through quiet
work, devoid of the spectacular that the best results will always
be accomplished. •
Of the jubilee meeting in 1902 we could write: "The Commer
cial Section seems to have taken a new lease on life in the Iast
two yeare and will soon demand a third session if this year's
enthusiasm is indicative of future progress." Though of progress
there were no striking signs, sufficient enthusiasm remained to make
the best of an unpleasant situation. The chairman was absent and

of a programme there was no superabundant evidence, yet the
temporary Chairman made the most of it. The fact that he was
ably supported by a small guard of faithful members augurs well
for next year when better things may be expected.
Much of the time was devoted to an informal discussion— a sort
of experience meeting— of a number of topics submitted by the
officers.
Papers read: —
J. W. McCorkle: — Management of a retail drug store.
First essential a knowledge of the business; early training under a com
petent, conscientious retail druggist; graduation from one of the best
pharmacy schools. Sufficient capital, carefully selected location, good well-
selected stock. Adeu.uu.te system of book-keeping, buy carefully, preferably
from the travelers as they stand between you and the jobber. Better be
known as a "high-priced druggist" than "a cheap one." Importance of
treating employees well, pay good wages, cheap clerks are high at any
price.
"A satisfied customer Ik the best advertisement." Holding old customers
frequently menus more than getting new ones. Physicians are desirable
and should be cultivated but not be allowed too great privileges. N<>
druggist should conduct a store without two or three of our best drug
Iournals, nor without affiliating with all the pharmaceutical associations,
local, state and national. Importance of sundries and side-lines. Necessity
for prompt collection of bills. The store that carries the stock and gives
the best service Is the store that will succeed. Remember "eternal vigi
lance" is the price we are called on to pay.
H. B. Mason: — Some common errors in business accounting.
First and Important essential Is the annual inventory. Depreciation in
stock. fixtures anil book accounts. Deductions, gross and net profits.
Proprietor's salary and total income. Freight charged with merchandise
Instead of e.vpense. Loss thru leaks in expense. Comparison of annual
statement with actual conditions.
J. S. (i leg horn: — Fire insurance.
Stock and mutual companies. Premiums. Standard form contract
Alleuatlon and assignment clause. Condition and "other insurance" stipula
tion. Lightning clause, re-insurance, co-insurance.
Section on Education and Legislation. This section hail
three sessions on Wednesday, the last of which was a joint session
with the Association of Boards of Pharmacy and the Conference of
Pharmaceutical Faculties.
The special feature of the programme consisted in the provision
made for the discussion of papers. The writer is decidedly in favor
of proper discussion. The mere reading of papers can be accomp
lished at home fully as well if not better. A paper is often of value
to the extent to which it brings about a spontaneous discussion.
However, even a good thing can be overdone. As soon as a discus
sion seems forced it only makes matters worse. If persons are
placed on the programme to discuss a certain paper not because
they have something to say but get up merely because they have
been requested and fill the allotted time with perfunctory remarks,
such discussion is of no value and had better be omitted.
One of the special features of the morning's session was the plea
that druggists purge themselves of the saloonkeeper in disguise.
There can be no doubt that no one feature of socalled social reform
is frought with greater danger to our calling than that which is forced
upon us by hysterical prohibitory movements througout the country.
If any feature of the afternoon session deserves special mention
it is the misuse urade of comparison made on the one hand between
such four year undergraduate courses in commerce as are given by
several universities, and the graduate course recently announced by
Harvard; and the courses in writing common business papers by our
pharmaceutical institutions on the other. Granted that our pro
spective pharmacists need a better business training, and granted,
that the druggists of this country are looking to our educational
institutions for imparting the necessary training, there is no
justification whatever in drawing the comparisons that, were made
by several speakers. To talk of a science of commerce is all right if
you yourself don't believe or try to persuade others to believe that
our pharmaceutical educational institutions are teaching such a
science at present.
The evening meeting was no such success as had been hoped for.
For a joint session of three associations, the attendance was poor.
Of the two papers read, the first alone- was of any importance. Its
value depended upon the influence its writer could bring to hear on
the members of the boards of pharmacy. But with few exceptions
these were conspicuous by their absence.
When the report of the Syllabus Committee was read, the exodus
became almost general. This report had been read at the meetings
of the Association of Boards of Pharmacy, also at the first meeting
of the Conference of Pharmaceutical Faculties. The members of both
bodies were unprepared to discuss it in joint session, since they had
not yet had the time to digest it at their own meetings. To listen to
a second reading of the report was too serious a strain on the
patience of many on a hot evening in a room t he atmosphere of
which was anything but stimulating. If these joint sessions are to
be a success, something else will have to be tried in the future. At
the first joint session in Indianapolis we succeeded very well in mak
ing the members of the boards suspicious of the teachers. ■ At the
PHARMACEVTICAL REVIEW. 29!>
present meeting we certainly (iid not succeed in attracting them.

Let us hope for better results next year. It will require patience on
the part of college men to persuade the members of the state boards
that our desire to cooperate is as unselfish as it is sincere.
Papers read:—
H. P. Hynson : — The importation of opium, coca and their alkaloids.
ThiH paper Herved aa a preliminary to a set of resolutions requesting
the national government to keep book over every parcel of these drugs
Imported and to trace it on its migrations to jobber, manufacturer etc. autl
ultimately to the consumer.
II. B. Mason: — Pharmacy facing a crisis — the temperance movement'
A very forceful and exhaustive paper on thiH important subject. It led
to the appointment of a committee which Is to report annually on the
progress of the prohibitory mo1ement and on itB influence on drug Htores.
Ij. F. Kebler:— The influence of the food and drugs act as an educator.
•willThe best the
educate result that can
general be in
public expected from the
the matter national law
of foodstuffs and isbeveruges
that it
and the physician in the matrer of medicamentH.
M. I. Wilbert: .The committee of one hundred and the American
Health League.
The paper reHnited in the adoption of a resolution commendatory of the
work being done and favoring ultimately the establishment of a national
bureau or department of health. Comp. this journ. vol. 25, p. 65.
H. Kraemer: The teaching of pharmacognosy.
*'In view of the problems that confront us anil that are constantly
arising, the aim first should ire the attainment of a definite and working
knowledge of the macroscopic and microscopic characters of the drugs
rather than a general knowledge of them. In other words, the student of
pharmacognosy should first of all be taught how to identify vegetable and
animal drugs in the crude, comminuted or powdered condition, to determine
their quality, and to prevent their deterioration."
J. P. Remington: — Commercial training in the teaching of pharmacy.
H. V. Amy: — Commercial training as applied to laboratory work.
H. M. Whelpley: — Pharmacopoeia! nomenclature.
The author urges that jobbers and others using old style nomenclatures
be requested to use pharmacopoelal nomenclature.
L. K. Say re: — The value of pharmaceutical advisory boards to state
boards of health.
0. H. Meeker: — The next step, or practicul plans for bringing the
physician and pharmacist closer together by clinical laboratory
work.
.1. T. McGill: — 1) The qualifications for licensure required by law
determined by the standard of pharmaceutical education. 2) Amend
ment of pharmacy laws.
The author points out where those pharmaceutical Institutions which
materially advance their courses over the requirements of the state boards
are at a decided disadvantage over those giving shorter and easier courses,
in the second part of this dual paper the author claims that most of th
arguments made for slow progress are fallacious. For the reasons givn,
the original paper will have to be consulted. *.
.100 PHARMACEVTIOAL REVIEW.
W. P. K a 1t1 merer : — Harmful effects of our pharmacy laws.

The author's claim is this, that insufficient examinations stump as
competent numerous persons who are utterly incompetent to be entrusted
with the life of their fellow men.. He fortifies his thesis with numerous
illustrations of events that have come under his observation.
The Historical Section is the youngest of the five sections.
It had the smallest and also the largest audience. Its technical work
will always have to be done by a few, its popular addresses are
interesting to everyone. Not courting numbers, it does not even
fear joint sessions with other sections. The reading of formal papers
is only a secondary feature of the programme. For the present, at
least, its main object is to collect and to stimulate others to assist
in this important work.
Papers read:—
T. T. Wilbert: — An interesting pharmacopoeia and some hospital
formularies.
The speaker presented a manuscript copy of a (ierman translation of
Hannoverian Pharmacopoeia of The original owner seems to have
been one Emll Seemann. information about this person Is desired. In
addition the speaker presented some more hospital formularies, muklng
comments about their character.
Q. H. Clark: — Sketch of Walter B. Kilner.
A short biographical account of the author of Kllner's Formulary, now
well nigh forgotten
Nellie Wukeman: — The photochemical work of Henry Trimble.
A brief review of this aspect of Professor Trimble's work. The paper
will appear in full in the next number of this journal.
L. F. Keller and V. K. Chestnut: — The drug collection at Washing
ton.
An historical account of the collection of drugs and medicinal plants in
the National Museum.
S. J. Hinsdale: — Early drug conditions in Connecticut, 1835.
A copy of a paper read before the North Carolina Pharmaceutical
Association in 18SU.
E. V. Howell: — Tea cultivation in North Carolina.
A collection of Illustrated articles and pamphiets.
E. V. Howell: — Early pharmaceutical laws of Great Britain.
A copy of references from the laws pertaining to the examination of
physicians in dioceses out of London. 14 & 15 Heary VIII, c. 5, para 3.
E. F. Ho well:— Synonyms of 1548, 1653 & 1761).
Copies of several sets of synonyms.
E. F. Howell: — The crude drug business in North Carolina.
Several documents bearing on the collection of crude drugs and their
com merce.
Edward Kremers: — The apothecary and related characters in Josl
Amman— Hans Sachs, "Beschreibung aller Stande auf Erden."
This account with reproductions will soon appear in this journal.
PHARUACEVT1CAL REVIEW. 301
Edward KremerH: — Some pharmaceutical book plates.

The speaker called attention to a collection of pharmaceutical ex llbrls,
pointing out the history of one and calling attention to the fart that Bo me
of the older pdarmaceutlcal treatises contain an abundance of Illustrative
material that will lend Itself to similar treatment. Reproductions of the
book-plates shown have appeared In this journal from time to time.
The Section on Practial Pharmacy and Dispensing had
a programme that vied in number of papers with that of the Scien
tific Section. The establishment of this section has proven a blessing,
not only to the Scientific Section which it has relieved of a number
of papers; but more still to the Association at large because it has
brought together the genuine pharmaceutical practitioners whose
interest in the Scientific Section was only half hearted. The growth
of this section, more than that of any other section, augurs well for
the future of pharmacy. The average pharmaceutical practitioner
will never be greatly interested in the cross section of a new drug,
or in the structural study of its alkaloid, valuable as such work
always must be. However, we have reason to be more than thank
ful if he sees in his calling something else than a mere means of
making a livelihood. The work of this section, if any, is likely to
create an enthusiasm for the professional side of his calling in the
young pharmacist. If we only had ten graduate scholarships for
each state providing the means for as many graduates to come to
the meetings of the American Pharmaceutical Association! Those
who are satisfied with the study of science for its own sake would,
no doubt, find the greatest inspiration in the Scientific Section.
Those, however, who are anxious to see how they can apply the
knowledge acquired at college, would undoubtedly receive sufficient
object lessons in this section to stimulate them to a continuation of
their scientific labors after commencement, i. e. in the every day
practice of their calling. It is in this particular that American phar
macy is weakest. It is here, therefore, that we doubly welcome every
forward step.
Papers read: —
W. Mittelbach: — Syrupus scillae compoeitus.
A recommendation that the directions for preparing this preparation be
altered to expedite the process of manufacture. The proposed changes in
the process are indicated.
1'. H. Utech: — Notes on syrupus aurantii aud syrupus acidi citrici.
Suggestions for modifications of the official processes of preparing the
same, whereby the keeping qualities thereof are materially Improved.
:I02 PHARMACEUTICAL REVIEW.
E. F. Cook: — The syrups of the U. S. P. (8th Rev.).

The official syrups have been prepared in the quantity prescribed in the
Pharmacopeia, with great care, and the directions therein followed minutely.
It has been the purpose of the writer to critically examine the details of the
processes and suggest improvements wherever possible, and also report
upon the keeping quality of the syrups during a period covering one year,
with samples kept under different conditions.
V. Schmidt: — Unguentum aquae rosae.
A revised formula for this ointment with working process for the same.
A formula used with perfect satisfaction for many years.
Charlotte E. Stimson: — Massage ointment or toilet cream.
Formula for "a white, creamy ointment that keeps well."
0. Raubenheimer: — Bismuthi hydroxidum.
Proposal a better title and nn improved formula for Bismuthi oxidum
hydratum N. F. Practical experiments and stoechiometrie calculations.
J. M. Good; — Notes and suggestions on some official cerates and oint
ments,
Including resin cerate, chrysarobin ointment, diachylon ointment, mer
curic nitrate ointment, yellow mercuric oxide ointment, ammonlated mer
cury ointment, tar ointment, zinc oxide ointment, manipulation of oint
ments in prescription work.
H. (t. Posey : —Compound solution of phosphate of soda, U. S. P.
Results of experiments to overcome the tendency of this preparation
to deposit crystals; also to avoid the growth of fungi therein.
(i. M. Beringer: — Fluidglycerates.
Suggesting a new class of liquid galenicals — 1 c. c. to represent 1 gm.
of the drug. Non-alcoholic — glycerin replacing alcoholic as u, solvent. Ad
vantages of this class of preparations over tluidex tracts. A general formula
with method of manipulation in mnmifacturing these products. Resuits of
experimentation upon a number of drugs; the results confirmed by assays
of the finished products.
M. T. Wilbert: — Some dosage forms of medicines.
Available methods for the administration of medicines. Forms in which
medicines may be administered. The need for adopting the dosage form to
the condition* and the idiosyncrasies of the patient. The origin of some of
the existing forms ot medicines and the need for elaborating and increasing
thls variety. Some dosage forms that should be developed and could readily
be exploited by the dispensing pharmacist.
W. C. Kirchgessner: — Useful formulae for useful people.
Several formulas are offered for consideration.
H. A. B. Dunning: — Some interesting prescridtions.
Collection of twelve copies of prescriptions recently filled in a retail drug
store. These were selected from a large number because of interesting
features observed while compounding, or where special treatment was re
quired to produce a more desirable finished preparation. They will be ex
hibited for general discussion without any suggestions as to how they
should be compounded by the collector.
.1. Wein stein: — Pharmacy's unexplored field.
The great possibilities awaiting the pharmacists in the field of bacterio
logy, whereby they can prove acceptable <o-workers with the physicians
and demonstrate their abilities as scientific men.
C. Lewis Diehl: — The evolution of "Unofficial Formulae.''
The object of this paper is to point out the slender ma terial upon which
the earlier efforts to secure uniformity in preparations of the same name
were based ; to trace the evolution of the earlier collection of formulas to
the magnificent collection now available to pharmacists; to reconcile the
younger members of our profession with conditions of imperfection which
were probably far more difficult to correct in the past than they arc at the
present time.
H. Blair: — Construction of official preparationn;

The U. S. P. being Intended to serve as a formula ibook ft>r pharmacists
and not simply a book of standards for manufacturers, should contain
formulae tha t are simple, plain and as exact as possible, : with a considera
tion for expedition and expense. Illustrated by samples. Improved formulae
offered. ^ ^
M. Apple: — Notes on several now elixirs.
Formulae and working processes for three new elixirs- The scant supply
of acceptable general vehicles 1H shown and the advantages of the suggested
ones are set forth.
I. V. S. Stanislaus: — A few laboratory notes.
Results of experimentation upon a few preparations with comments.
O. Kauben hei mer : — Linimentam nmmoniae.
Advantages of an ammonia liniment, prepared by shaking together
oleum sTsiuiil and aqua ummoniae. over the U. 8. P. formula and directions
for preparing the same. A practical demonstration. Results of extensive
experiments with a large number of oils. Historical data on various am
monia liniments.
YV. L. Cliffe: — A method of preparing lime water that ensures con
formity with the U. S. I*, requirements.
A simple, inexpensive plan for preparing lime water U. S. 1'. A modifi
cation of the official directions of manipulations.
F. W. Ni tardy:— Formulas recommended for introduction into tne
N. F.
Formulas and methods of preparing several new preperations.
II. G. Posey: — Dispensing and laboratory notes.
A medley of prescription and laboratory notes gathered in practical
experience; also several formulae for new preparations, and suggestions for
methods revising working processes of several official preparations.
0. Raubenbeimer: — "Safety benzin."
A reply to query No. 2'"\ of the Pennsylvania Pharmaceutical Association,
1908, list of queries, viz.: What satisfactory formulas for cleaning fluids for
fabrics, etc , can you suggest which are cheap and not dangerously inflamm
able. History of safe bentin preparations.
\V. Mittelbach: — A plea for real pharmacy.
A remonstrance against the tendency to Increase the number of com
pound preparations to he called to the attention of the medical men. An
appeal for greater simplicity in medication, suggesting that the physicians
indicate. which combinations of drugs are most desirable, by writing original
formulas for the same in the form of individual prescriptions.
J. T. Harbold: — The opportunity of the hospital pharmacist in ad
vancing the U. S. P. and N. F. propaganda.
The great possibilities open to the hospital pharmacists in advancing
the propaganda efforts in behalf of the U. 8. P. and N. F. by taking ad
vantage of the intimate relationship that exists in those institutions
between the internes and the pharmacists.
F. E. Niece: — Some chemical reasons why solutions deteriorate.
The causes for many solutions deteriorating from chemical changes, to
gether with recommendations how to overcome the same.
J. L. Lascoff: — The professional and commercial pharmacist.
A remonstrance agalnBt some of the customs of the day, as seen in
N. Y. City; also an appeal for greater professionalism in our commercialism.
In any other section the absence of the Chairman for two con
secutive years might prove a serious matter. In the Scientific
Section his absence is scarcely noticed. While we regreted to
learn the cause of the absence of our Chairman, the Secretary for a
second time presided ably , over the two sessions. Mere justice de
manded his advancement to the chairmanship for next year. The
general run of the papers was good. The most satisfactory aspect
of the programme consisted in the number of papers read by younger
members. When the officers are in a position to remain indifferent
about half a dozen papers offered, the section may be congratulated
indeed. If one recalls that the class of papers now read in the
Section on Practical Pharmacy and Dispensing were formerly pre
sented to this section, one can appreciate the length of the pro
gramme had this younger sister section not been established several
years ago.
Papers read: —
H. H. Rusby: — Crude and powdered drugs at the port of New York
during the year 1907—8.
Illustrated by specimens.
H. M. Gordin: — On the crystalline alkaloid of Calycanthus glancus.
Third paper.
On lsocalycanthine, Uomerio with ealycanthine, and its salt*. The paper
includes u paragraph on Its crystallography by Dr. E. H. Krauss.
A. It. L. Dohme and H. Engelhardt: — Oil of sandalwood.
Ueply to papers by B. J. Parry and Schimmel & Co. on the value ol
optical rotation as a test o( purity. Authors have controverted arguments
of these two authors and offer, besides their own experience, the experience
and results of two other large distillers of this oil, in favor of reducing the
optical rotation of the Q. S. F. on sandal oil. Authors maintain that
assay of santalol, the active principle, solubility in 70 per cent alcohol, and
specific gravity are ample to define a pure oil, but see no objection to in
cluding the acid and saponification numbers to recognUe adulterations. If
optical rotation must be iucluded. then lower it to —12° as a minimum
requirement, so as to avoid ruling out much of the oil now distilled, per
fectly pure, and meeting all requirements.
A. R. L. Dohme und H. Engelhardt: — Purity of some official and
non-official drugs and chemicals.
An examination of about lo,000 drugs and chemlcalB was made and a
report is glveu of those that did not measure up to lequirements. The re
sult shows a marked Improvement in quality of goods examined since the
passage of the Pure Food and Drugs act. Among the drugs not usually
attaining standard requirements may be mentioned asafetida, ergot, hyos-
cyamus, jalap, croton oil, oils of eucalyptus, bitter orange, and savin. A
Btrong recommendation Is again made for incorporating in the U. S. P.,
1910, a "Chioroform pro narcosl*' as very few if any on the market meet
the requirements of such a product. A digestive strength test for papain is
suggested to be made official. Resin scammony made from the roots of
scammony or orizaba root is suggested to be made official, as the virgin
scammony was found to be practically off the market. Saffron should be
returned to the U. S. P., as it Is used considerably and Is frequently
adulterated.
H. K raem er: — The difference in the structure of belladonna and
scopola.
Having occasion the past summer to examine both belladonna and
Hcopola, and owing to the frequent admixture of belladonna root with
scopola rhizome and the reports that belladonda leaves are sometimes ad
mixed with scopola leaves, It seems to the author to be desirable to present
the resultH at this time.
Belladonna Root.—In addition to the character which have already
been described. It was found that many of the tracheae have bordered
pores, which character has apparently been overlooked by previous investi
gators, but which serves to distinguish belladonna from scopola.
Scopola Rhizome and Roots.— While the starch grains and crypto-
crystalline crystals of calcium oxalate are not wholly identical in appearance
with those in belladonna, they are quite similar, the crystals frequently
occuring in rosette aggregates. The tracheae have reticulate markings, and
are rather short and broad, thus being readily distinguished from those in
belladonna. Wood fibres are usually present "in belladonna, but are not
found tn scopola.
Belladonna Herb. — This drug has three principal distinguishing
characteristics: (a) The calyx lobes are rather long and spreading, expos
ing the berry; (b) the hairs on the leaves, while not numerous, are of
relatively frequent occurrence; (c) some of the tracheae, particularly of the
stems, ha ve bordered pores.
Scopola Herb. —The calyx lobes are relatively short, and the berry is
almost completely enclosed by the calyx tube. A very few glandular hairs
may with difficulty be found. In addition to the tracheae with annular
markings and those with simple pores, there are tracheae with reticulate
markings.
W. A. Puokner and A. H. Clark: -The estimation of phenol.
An estimation of phenol in tablets containing, besides phenol, also bis
muth subnltrate, opium and aromatic powder, was called for in connection
with the work En the Chemical Laboratory of the American Medical
Association. Experiments attempting to separate, by means of solvents,
the phenol from other constituents prior to its estimation were abandoned
in favor of methods wherein the phenol was separated by distillation.
Liberation of the phenol prior to its distillation by menus of phosphoric
acid was found to be objectionable in that nitric acid from the bismuth
subnltrate was liberated and interfered with the estimation of phenol.
Finally, a method was adopted in which the mixture containing the phenol
was treated with an excess of alkali, the phenol then liberated by satura
tion of the solution with carbon dioxide, distilled, and estimated by the
U. S. P. method as tribromphenol.
F. R. EIdred: — Sampling of drugs and preparations for assay.
F. R. Eldred and C. M. Pence: — Notes on the estimation of hydrastine.
Purity of the hydrastine obtained in assaying golden seal by different
methods. The estimation of hydrastine in glycerin solutions.
F. K. Eldred and W. C. Bartholomew: — A note on the separation
of emulsions for analysis.
Practically all emulsions may be separated by alcohol in such a manner
that the oils, emulsifying agents, and other ingredients can be accurately
determined and examined. Results Illustrating the accuracy of the method
are given.
H. V. Amy and O. H. Dawson: — Solution of chlorinated soda.
A critique of the process of manufacture of this product as given by the
U. S. P., VIII, showing that solutions prepared by this process yielded
respectively 2.01, 1.65 per cent and 1.65 per cent available chiorine, despite
the fact that the amount of chiorinated lime used was increased to represent
the pharmacopeia) content (HO per cent). Report of experiments with
modifications of the process of the Pharmacopeia of 1880, by which the
chiorinated lime paste is mixed with sodium carbonate solution and the
filtrate collected. In three experiments, 12 gm. chiorinated lime (26. 7 per
cent) and 6.5 gm. monohydrated sodium carbonate were used, the difference
in methods being in the amount of water employed and consequently the
amount of filtrate obtained; the quantities of filtrate being 25 c. c., 48c. c.
and 90 c. c. respectively. In the fourth experiment, a tenfold recipe was
used and 900 c. c. filtrate collected. The four finished solutions assayed
respectively 3.05 per cent, 2.50 per cent, 2.67 per cent, and 2.85 per cent
available chiorine.
H. A. B. Dunning: — Proteid compounds of heavy metals.

A collection of notee on the preparation of compounds of albumen anil
peptonized albumen with iron, mercury, silver and copper. Referring to the
... iron compounds, various methodH were used to produce them. The object
of the experimental work was to devise satisfactory processes for the produc
tion of Holuble compounds. To accomplish this, various chemical sub
stances — sodium hydroxide, sodium citrate, ammonium citrate and man
ganese citrate — were employed to promote solution.
L, K. Sayre: — A further study of the alkaloids of gel*emium.
A brief review of former work, upon the constituents of the drug, by
the author. A review of Thompson's work on gelsemine and gelseminine.
Further progress in the investigation of these two alkaloids of Thompson,
by employing 40 pounds of the drug from which the alkaloids were
extracted and the resulting principles examined. Physiological tests made
of the products. A process for the assay of gelsemium preparations is also
suggested.
E. Sander: — The superiority of artificial mineral waters.
Origin of mineral waters. Meteoric water penetrates the earth's crust
and returning to the surface loaded with materials, creates healing springs.
Beneficial only on their source. No uniformity of composition at different
times. Easily decomposed by various causes. * Cannot be bottled or trans
ported. Dr. F. A. Struve constructs apparatus for prepariug artificial
waters of same composition as the natural but without its disposition to
deterioatiou. Proof by public exhibition. Scientists of all countries indorse
the mvention. Opposition active but vain. Struve in the lead. Necessity
for pure materials. Artificial waters a great success.
H. Engelhardt and II. W. Jones: — The detection of phenol and
cresotic acids in saliscylic acid and its derivatives.
The Carlettl reaction for the detection of phenol in salicylic acid by the
use of a 2 per cent alcoholic solution of furfurol was applied to a number
of samples of salicylic acid and its derivatives. The investigation was
extended to discover whether this reaction is also applicable to cresotic
acids which are formed during the process of manufacture of salicylic acid.
The authors find that the cresotic acids give the same color-test as phenol
with Carletti's reaction, the sensitiveness being even greater than with
phenol. Of eighty samples of salicylic acids and derivatives, only 60 per
cent were found free from contamination.
H. W. Jones: — Notes on syrup of hypophosphites and syrup of cal
cium lactophosphate.
The results of a study of the progressive [inversion taking place in the
above-named IJ. S. P. syrups. These results, presented in the form of curves,
show the rate and extent of this inversion in Syrup of Hypophosphites,
U. S. P., and Syrup of Calcium Lact .phoHphate, U. S. P., and in experi
mental syrups containing varying amounts of either mineral or organic
acids. It was found that all the cane sugar of Syrup of Calcium Lacto
phosphate, U. S. P., was inverted, under ordinary conditions, within twenty
weeks, while 11) per cent of that contained in Syrup of Hopophosphites,
U. S. P., is inverted in the same time.
V. Coblentz and 0. B. May: — Comparison of volumetric methods for
the estimation of phosphoric acid.
A critical review of the various volumetric methods which have been
proposed for the estimation of phosphoric acid, with view to adaptability
to the requirements of the U. S. Pharmacopeia. The methods employed
were as follows: (1) Uranium Acetate; (2) lodometrlc. Christlnsen ; (8)
Estimation of uncomblned excess of standard ammonia V. S. added in con
junction with magnesium sulphate; (4) Solution of Ammonlo-magneslum-
phosphate in measured excess of N/10 acid V. S. and titration of the liber
ated phosphoric acid: (5) Estimation by N/10 silver nitrate V. S. after
converting into a bi-phosphate ; (ti) Titration with N/25 calcium
hydroxide V. S. in presence of sliver nitrate; (7) Precipitated a silver phos
phate in presence of calcium hydroxide, dissolved in nitric acid, and estim
ated according to Volhardt: (8I Same as 7, employing residual titration of
the excess of N/10 silver nitrate V. 8.; (9) Silver Phosphate precipitated
in neutral (not alkaline) solution In presence of measured excess of N/10
sliver nitrate V. S. which is in turn titrated according to Volhardt. Cry
stalline phosphoric acid has the formula of 2H3PO4.H2O fuses between
31° and 32° C., specific gravity 1.7563 at 25° C.
V. Coblentz and (). B. May: — Deterioration of hydrocyanic acid.
The deterioration of this acid, prepared from potassium ferrocyanide and
also Bilver cyanide, wax (studied under various conditions with the following
results: Diffused tUht plays no Important part in the decomposition. The
employment of 50 per cent alcohol us a medium serves as an excellent pre
servative, as well as the employment of a 1 per mille solution of ncetanilide
or aclulncatlon with an inorganic acid. Prussic acid is best preserved in
paratllneil bottles where every contact with glass Is avoided, the loss
amounting to about 6 per cent in nine months. Decomposition is brought
about through the presence of alkali cyanides, especially ammonium cyanide.
V. Coblentz and 0. B. May: — Quantity of arsenic in bismuth salts
and testing same for arsenic.
The authors advise against the use of nitric acid in the ignition of the
various organic salts of bismuth previous to testing for arsenic, owing to
the difficulty encountered In removing the last traces of nitrate from the
nsh.
This ash, when boiled with a solution of potnssa and filtered, to remove
the bismuth, gives up its nitrate which, when acidified and introduced into
a Marsh-IIerzelius or any form of apparatus based on the generation of
arsine gas, causes the decomposition of the latter. Slmple ignition of bis
muth salts does not cause any loss in arsenic content. Quantitative estim
ations oT the arsenic content of twenty-five samples of commercial bismuth
salts were made, among which there were six free and two with barest
traces of arsenic, while the remaining contained from 0.05 to 0.2 parts of
arsenous oxide per 100,000.
J. Feil:—The acetic acid fluid extracts of the U. S. P., VIII.
These preparations keep well, but lose acidity on standing, the loss
varying for each fluid exlract. Their odor improves. It is thought that a
large number of this class of galenicals would find extensive use in veterinary
practice. It Is suggested that a veterinary surgeon would be a valuable
addition to the revision committee of the next Phaemacopoela, as druggists
are finding an increased demand for medicines intended for domestic animals.
It is further suggested that a similar line of arguments could be applied to
the dental profession and a D. D. S, be made a member.
10. N. Gathereoal: — The percentage of moisture in commercial starches.
F. X. Moerk: — Classification of the quantitative statements of the
IT. S. P. (8th revision).
A. B. Lyons: — Notes on Liquor potassi arsenitis.
A. B. Lyons: — Alcohol table to facilitate rapid approximate deter
minations of alcohol by apparent specific gravity.
L. F. Kebler and V. K. Ches t u ut : — The National Museum in drug
research.
L. D. Havenhill: — The desirability of more elaborate pharmacopoeial
standards.
L. F. Kebler and F. P. Morgan: — The harmful effects of acetanilide,
antipyrine and phenacetine.
(J. E. Vanderkleed and L. H. Beruegau: — Interference of sodium
bicarbonate in the testing of pancreatin.
Although pancreatin is supposedly most active in alkaline solution, the
presence of sodium bicarbonate seriously interferes with its auiylolytic
action, as shown in the assay of Compound Pancreatic Powder, N. F., and
other mixtures of pancreatin and sodium bicarbonate, unless the latter be
first neutralized with acid.
Deterioration of Some Standard Pharmaceuticals.
By H. E. Barnard.*
In the operation of a laboratory devoted to the enforcement

of the pure food and drug laws, many problems constantly arise.
Some of them concern manufacturers ethics, others simple honesty,
others the method and technique of production and distribution, and
still others involve purely chemical problems that can only be under,
stood and adjusted after study in a laboratory. The chemist who
deals both with food and drugs is confronted with very puzzling
conditions. Until recently there have been no standards of composi
tion for foods, while the character of drugs has been carefully
regulated for more than eighty years. The national Pharmacopoeia,
since its first publication in 1820 has been accepted by pharmacists
and physicians alike as authority upon drugs, their method of assay
and their standard of purity. Druggists are as a class educated
men. Most of the states require that every drug store have in its
employ a registered pharmacist or a man who has had special train
ing of a collegiate grade t which is designed to prepare him for his
work. Indeed the druggist looks upon his business as a profession,
and holds that it takes rank with that of the physician. In view of
these facts it would be supposed that the examination of standard
pharmaceuticals would show but little departure from the standards
laid down in the United States Pharmacopoeia or those equally
reliable and valuable authorities, the U. S. Dispensatory and
National Formulary. A brief study of the results obtained in any
laboratory devoted to the assay of the medicinal preparations pre
pared and dispensed by the drug trade, shows a surprising departure
from these conditions. To be specific, in my laboratory during the
Iast two years we have analyzed several thousand common prepara
tions which are found in every drug stock and are constantly dispensed.
We have, for instance, analyzed 330 samples of Tincture of Iodine.
We have found of that number but 113 to contain the amount of
iodine required by the Pharmacopoeia, namely 6.86 grams of iodine
to 100 cubic centimeters 65.77c of the samples contained less than
• Chemist to State Board of Hualth and State Food and Dtug Commissioner
of Indiana.
t Uniortunatoly thls is not the case. E. K.
this amount. Of 226 samples of Spirits of Camphor analyzed but

26.1'/r. contained the required 100 grams of camphor to the liter of
solution. Of 251 samples of Tincture of Ferric Chloride but 29.9%
contain 13.28% of the anhydrous salt, corresponding to 4.58% of
metalhc iron. Of 236 samples of Lime Water analyzed but 52.5%
contain .14 of 1% of pure calcium hydroxide. This departure from
the standards as set forth by the druggist's authorities are so ab
normal that the analyst is compelled to accept the fact that some
conditions other than that of fraudulent intent or gross carelessness
must obtain. In order to arrive, if possible, at the correct season
for the low grade of these and other standard preparations it has
been our custom not to prosecute at once the druggists dispensing
the impure article but to correspond with him for the purpose of
determining why he violated the law by the sale of impure goods.
To this end we have sent out many hundred letters and have received,
almost without exception, very prompt replies, but strange to say
an analysis of these replies throws but little light on the question
and offers no solution to the problem. Of course many dealers
employ old formulas, others lay the blame upon the wholesaler.
But few admit carelessness either in preparation or storage. The
most general explanation the druggists offer is that the goods have
deteriorated since their preparation. We cannot control from a,
laboratory the technique of manufacture at the druggist's store, the
use of old formulas or the employment of crude material, nor can
we compel the druggists to adopt new formulas. If, however, it is
a fact that druggist's preparations deteriorate in storage and that
they have no control over this cheapening of the quality of their
output, Cue chemical laboratory can offer assistance and determine
what goods do deteriorate and under what conditions, and can
suggest methods of handling which will prevent such deterioration.
To this end we have been studying for somet ime past a series of
standard preparations prepared exactly as directed in the Eighth
Decennial Revision of the (I. S. 1'harmacopoeia from pure chemicals,
and kept as closely as possible under the same conditions of light
and temperature as obtain at the ordinary drug store. The results
of this investigation are most interesting. The drugs studied were
Tincture of Iodine, Lime Water, Ammonia Water and Spirits of
Camphor.
The Tincture of Iodine was prepared by triturating 70 grams
of iodine and 50 grams of potassium iodide to a coarse powder and
transfering it to a graduated flask. The mortar was rinsed with suc
cessive portions of !)5% alcohol which was poured into the flask
:*lo PHARMACEUTICAL REVIEW.
Alcohol was then added until the finished product measured one liter.
The solution was complete at the end of the second day. This
tincture so prepared assuyed 101.2% U. S. P. strength, calculated
upon a basis of 0.86 grams of iodine to 100 cubic centimeter.
The solution was then divided into five portions of 200 cubic centi
meters each. One portion was placed in a glass stoppered reagent
bottle and wrapped in black paper: the second portion was placed
in a similar bottle but was not protected from the light; the third
portion was placed in a similar bottle and exposed to the direct
sunlight. Another portion was placed in a bottle stoppered with an
ordinary velvet cork, and the final portion was placed in an un-
stoppered bottle. Two weeks after preparation the contents of each
bottle was analyzed. Practically no change was noted in the com
position of the first four samples, but the sample which had been
left uncorked had increased its strength about 4%. One month after
date of preparation, the first four samples were exactly the same as
when made, but the oth sample had incieased its strength 7"A. Two
weeks later no change was noted except with the last sample which
was now 112.69< [J. S. P. and two weeks later, or two months after
manufacture, 121.1% U. S. P. Ten weeks after manufacture an in
crease of strength of about 1% was noted in the first four samples.
The uncorked sample had, however, increased to 127.795 and two
weeks later to 136.1%. Two weeks later while no change was noticed
in the first four samples, the 5th sample registered 147. 89'i, and
when the preparations were four months old the 5th sample had
concentrated to 15794. In the next two weeks its stre. gth was
172.8%, at the end of 5 months 189% and at the end of 7 months
the iodine content corresponded to 306.0% U. S. P. No precipita
tion of iodine was noted in the bottom of the bottle, nor was there
any appreciable sublimation upon the sides of the bottle, although
a slight amount of potassium iodide deposited in the neck of the
bottle. Upon dilution in five volumes of water the solution was still
perfect. At eight months since the work was started the bottle #1,
tightly corked and protected from light, registers 102.395 , an increase
of 1.1% over its original volume. The second sample, unprotected
from light is the same, the third sample exposed to direct sunlight
now reads 10.'!. 4%, an increase in strength of 2.29!. The fourth
sample kept in a corked stoppered bottle now reads 103.8%, an in
crease in strength of 2.091 . These figures are exactly contrary to
the views held by the drug trade. So far as we can determine it is
t he opinion of dispensing pharmacists that Tr. of Iodine deteriorates
upon standing, and that the iodine volatilizes so that at the end of
TINCTURE IODINE
320 4f 1i ii 1 D_ 12 14 16 18 20 22 24 2S 2
300 I
LEG END
1B0 1234 — — — . - - /
/
5
/
2(0
240
220
200 /
1
1*0 /
/
1(0 ///
/
140 V
120
100
The Humberk 100 to i!50 represent percentages T'. S. P.
The numbers 2 to 28 Indicate weeks.
The numbers of the legend, vlt. 1 to Fire thojIe of the preparations mentioned
in the text.
six months an appreciable less amount of iodine will be present than

when freshly made. On the contrary so far as we have observed
there is no volatilization of iodine, but a very marked concentration
because of the evaporation of alcohol from the unprotected
solution.
Spirits of Camphor was made by dissolving 100 grams of pure
camphor in 800 cubic centimeters of 95% alcohol, filtering and
adding sufficient alcohol through the filter to make the volume of
the finished product one liter. The Spirits of Camphor so prepared
when analyzed was found to be 98.3% U. S. P. strength. The
method of analysis employed was to observe the reading in a 100
millimeter tube in a Schmidt <Sc Haensch triple field polariscope,
accepting as a basis for reading the fact the Pharmacopoeia pre
paration of Spirits of Camphor will show a plus reading of 12 under
similar conditions. The solution was then divided into five portions
and placed in the same style of bottles similarly protected as in the
case of the Tincture of Iodine. At the end of two weeks there was no
change in the first four samples: the fifth sample, had, however, in
creased in strength 5%. Throughout the experiment which extended
over twenty-two weeks and involved 12 analyses of each sample,
there was no appreciable change in the character of the first four
samples. The fifth sample, however, increased in strength rapidly
and at the end of eight weeks it was 119% U. S. P., at the end of
12 weeks 134.1%, at the end of 10 weeks 157.57c, at the end of 20
weeks 185.0% and at the present time reading 259.17%. The in
crease is not rapid at first but as the solution becomes more con
centrated the volatilization of the alcohol seems to take place more
rapidly so that while the percentage of increase was low the first
two weeks, the percentage of increase at the end of 1H weeks was
11.6, 20 weeks 15.!), 22 weeks 21.6, and a graphic representation of
these figures shows these changeB very vividly. As in the case of the
Tincture of Iodine, the drug trade is of the opinion that Spirits
of Camphor loses strength because of volatilization of the camphor
gum, and again our results show that opinion, we believe, to be
entirely erroneous. We have noted no volatilization or deposit of
camphor on the sides of the bottle. The solution is still perfect and
to all appearances the only change in the preparation has been that
caused by concentration of the solution due to volatilization of
alcohol.
PHARMACEUTICAL REVIEW. 3l:i
SPIRITS CAMPHOR
i\ % 1p
1 12 14 t i0 22 21 ;e 2
/
/
LEG END
/
12 3 4 — -
5
I
. - —■ — — - — —
The mimberN !l5 to 2(10 represent peroentnges V. H. P.

The numberH \l to 2M indicate weeks.
The numlxTw of the legend, vlz. 1—5, are those of the preparationH mentioned
in the text.
Phvtochemical Xotes.
Crom the Laboratory of Edward Kremers.
69. Quantitative determination of oxidase in the leaves
of Monarda fistulosa.
By XelHe Wakeman.
Previous experiments* have shown the presence of an oxidase in
the leaves of Mouurda fistulosa, also the capacity of this ferment to
oxidize the bydrothymoquinone found in this plant to thymoquiuone,
thus giving rise to thymoquinhydrone and thereby explainiu<^ the
formation of this pigment in plant and oil obtained therefrom. Iu
a second series of experiments! the thermal death-point of this fer
ment was ascertained. The object of the experiments now to be
recorded was to ascertain the relative amounts of oxidase, which
has the capacity to eliberate oxygen from hydrogen peroxide, in
Monarda leaves under varying conditions of growth.
The tests were made at intervals of seven or eight days during
the period from August 7 to October 5, 1!)07.
The tests of August 7 and 8 were made with leaves collected at
Wingra Park, Madison, Wis., where the plants grew in open, hilly
places fully exposed to the sun. Tllose °f August 15 to September
23, inclusive, with leaves from plants collected in shady places along
the roadside at Columbus. Wis., while the leaves used in the tests
of September 28 and October 5 were collected along University Drive.
The leaves collected at Columbus seemed much more fresh and pulpy
than any from the Madison plants. Perhaps this accounts for the
difference in the results.
Date ot Col Amount of gas In cc. îven off after - minutes. Place
lection ami of
Experlment 10 15 80 45 BO 75 1)0 120 Collection.
28 31) 40)4 43)4 45 45)4 Madison
8 24 31 30 43)4 47 48 "
" 15 53 70 85 94 100 102 Columbus
" 23 31 51 04 74 83 87 !)1 94 96 .i
" 31 20 4-2% 52 M% 71 77 82 84 85
September 0 4* 66 70 85 94 102 104 104'4
14 40 65 70 83)4 91)4 99 101
23 :t»i 55 67 87 94 '.)»% 10.1 i*
28 2.'. M% 30 43 47 52 53 Madison
"
* Ictober 5*.. 23 30 35 43 44% 40 47
In all the experiments tabulated above one half gram of fresh
leaves reduced to a pulp was treated with 20 c. c. of hydrogen per
oxide. At the end of 75 minutes all action had practically ceased,
the greater part of the oxygen — about % of the entire amount —
being given off during the first 15 minutes. The flask containing
the oxidase was frequently shaken, otherwise but little oxygen was
given off.
* V. Kanak, this journal, vol. 22, pp. 190.
t D. B. Swindle. Ibidem, vol. >2, pp. 198.
The leave* collected on the morning of October 0. wen' covered

with frost.
In performing the experiments recorded in the foregoing table
leaves that had attained to about their full growth but were still
fresh and vigorously growing were selected. It was noticed in the
first five of these and also in some other tests that were made, that
where the leaves were greenest and gave the best evidence of vigorous
growth the largest yield of oxygen was obtained. To test this the
following determinations were made with material collected at
Columbus.
Leaves, lower down on the stem, that had reached their full
growth and, while not possessing the dark green color indicative of
strong growth, yet had no brown spots and dry edges, were chosen
with the following results.
OLD LEAVES.
Date
5 ruin. 1 <> min. If) mln. 3D mln. 4."> mln. 60 mln. 75 mln.
.. 19 27 33 38J4 43 44 44
14 17« 24 29« 34 38 m 40
23 .. 17 ti4tf 30 35 39 41 42
The leaves collected August 2.'l and 31 were from a little patch
of monarda where there were several plants whose leaves and stems,
while fresh and giving evidence of strong rapid growth, were deeply
colored with the purplish red, that is often found in monarda.
Fresh vigorous leaves, from the top of the plant deeply stained with
the red. were selected and treated exactly as the green.
ltED LEAVES.
Date
"> mln. | 10 mln. 15 mill. HO mln. 45 mln KO mln. 75 mln.
August 23 21 20 31 32X 35 35K
31 19 22 25 26 27)4 29 2!i)4
On August in and 2i{ the colored florets were collected and
tested, taking care that no green parts entered into tne test. After
August 31 the maturing of the flowers and a heavy rain made it
impossible to secure more blossoms. In 15 minutes the action was
practically over.
BLOSSOMS.
Date.
5 mjnates. 10 minutes. 15 mlnut«B. ;10 minutes.
ex 8 9 10
23 4« 7 9
At the time of collecting leaves for the foregoing tests, each time
from 50 to 100 grams of leaves, as nearly as possible like the fresh
leaves tested, were gathered, weighed, carefully dried, there weighed
again and dated with the date of collection for comparative tests
of the fresh and dried leaves.
Literary.
Books Reviewed.
The art of dispensing. By Peter MaeEwan. Published by The
Chemist and Druggist. Eighth edition, 542 pages.
The arrangement of the present edition is similar to its prede
cessors and contains much valuable advice upon the materials and
methods employed in dispensing. The 16 pages on prescribes and
dispensers many be read with profit by physicians as well as phar
macists. Full directions are given for the manufacture of extempo
raneous preparations generally, such as pills, suppositories, emulsions,
ointments, etc. Twenty-six pages are devoted to special drugs and
conveniences in dispensing, 13 to incompatibility, 20 pages to Ger
man and French prescriptions, most of which are autograph copies
accompanied by a transcription and a translation. There are also
23 Latin-English autograph prescriptions with transcriptions and
comments. The portion devoted to new and unofficial remedies
has been somewhat enlarged making a very complete list. The
physical appearance, solubility, use and dose of each are given.
There are 52 examination exercises, as given by the Boards of
Examiners in Edinburgh and London. Each exercise includes from
3—5 prescriptions and one galenical preparations to be made.
Five pages are devoted to homeopathic pharmacy especially as
conducted in England. The appendix contains prescriptions, abbre
viations, terms used in French and German preparations, tables of
doses, etc. .1. B. Stevens.
DlE ("HEMIE UND BlOLOOIE DER PFLANZLICHEN SeKKETE. Fill Vor-
trag von A. Tschirch, 0. Professor an der Cniversitilt Bern.
Brochure, pp. 95. Akademische Verlagsgese Use haft
m. b. H., Leipzig. 1908.
The work in any department of chemical investigation advances
at such a rate now-a-days that even the specialist may not keep up
with the details. Whenever such a special treatise as e. g. the
"Harze and Harzbehiilter" appears we are exceedingly thankful to
the author for such a detailed monograph, we purchase it at the first
opportunity, and place it on our shelves for future reference. We
know then just where to go to find an answer to many a specific
question, but we remain ahout as ignorant as to the exact status

(1uo of the branch of our science covered by the new treatise as wp
were before.
Fortunately, there appear from time to time essays or lectures
which present a summary of the work accomplished in recent years
and which even afford an insight into the progress that may be
expected in the future. Such a picture of the recent past and im
mediate future, so far as resins are concerned, we find in this lecture
delivered before the Swiss Chemical Society. Possibly no one was bet
ter fitted to give such a retrospect than the author of the ''Harze und
Harzbehtilter", to which it is an admirable supplement. Every one
active in plant chemical resenrch will want to read it. It is not
only meant to be read, but constitutes interesting reading. E. K.
Handbuch der Pharmakoonosie. Von Dr. A. Tschirch, Professor
der Pharmakognosie etc. an der Universitat in Bern. Erste
Lieferung, pp. 64 mit zahlreichen Abbildungen. Verlag von
Chr. Herm. Tauchnitz in Leipzig. 1908. M. 2.00.
There is almost a plethora of text-books on pharmacognosy
treated from the botanical view-point, in the English, German and
French languages but there is nothing in any language that is
modern, authoritative, and exhaustive, which treats of pharma
cognosy in its broadest sense. This want is to be met by the refer
ence work under consideration, and those who have had the privilege
of working with the author or those who have kept in touch with
his writings and researches upon topics pharmacognostical, will
agree that there is no one so well fitted for the task as he. Professor
Tschirch is not only an enthusiast for pharmacognosy, but he is a
wonderfully endowed, indefatigable research worker and director.
For twenty-five years he has devoted his energies in the development
of his favorite subject and has all this time doubtless had in mind
the preparation of a monumental work that would not only be an
honor to him but to the science. Ever since his connection with the
Pharmaceutical Institute of Bern he has directed large numbers of
students from all quarters of the civilized world in unsettled problems
in pharmacognosy. His researches on the difficult subject of resins
fill a large volume, and his publications upon different branches of
botanical-pharmacognosy run into the hundreds. Furthermore, he
has travelled extensively in tropical countries for the purpose of
studying methods of cultivating, harvesting and preparing drugs
for the markets of the world. Being an expert photographer he has

made countless pictorial records of these various operations that
are not only interesting but often more instructive than pages of
text. Everything which the author undertakes is with a thorough
ness that commands wonder and admiration.
This epoch-making contribution to pharmacognosy is to be
published in about 30 parts in 4 volumes. The book will be divided
into two great parts, viz. General Pharmacognosy and Special or
Specific Pharmacognosy. The earlier numbers or parts discuss most
thoroughly the definition and problems of pharmacognosy; the
materials of pharmacognosy; cultivation, collection and treatment
of medicinal drugs; the transportation routes during ancient times,
the middle nges and the present; drug auctions; drug control;
export lists; treatment of drugs at receiving stations; weights and
measures used in world's commerce; trade names and varieties; and
methods of packing drugs.
The various pharmacognostical systems employed in text-books
are analyzed in detail, and reference books, proceedings, year-books,
and commercial reports in which material of interest to pharma
cognosy may be found, are reviewed.
Instruction of pharmacognosy by lecture and laboratory is given
considerable attention. The prospectus states further that applied
pharmacognosy, as, for example, the testing of drugs for identity,
purity, adulterations, and substitutions will receive due share of
treatment.
The various sciences which play a part, in the broader conception
of pharmacognosy are fully discussed, viz. Botany; Zoology;
Chemistry; Physics; Geography; History: Ethnology; Etymology:
Agriculture.
In the second great division of the work plant and animal drugs
are exhaustively treated. An idea of the thoroughness of treatment
may be gained from the ten pages devoted to the specimen drug
CbondniB. It is the plan of the author to consider each drug as far
as possible under the following headings: Name, Synonyms, Ety
mology of the name, Botanical source (Etymology), Systematic
classification, Description, Geographical distribution, Cultivation,
Collection of drug, Transportation route and trade varieties, Mor
phology, Anatomy, Chemistry, Pharmacochemical-pharmacological
classification, Admixtures, Adulterations, Uses, Tests, History,
PHARMACEUTICAL REVIEW. :\V.)
Parallel drugs. A very complete bibliography is one of the valuable

features.
The text is very carefully and accurately written, and in a style
that is pleasing and easily comprehended. Numerous illustrations,
all of which are excellently reproduced from photographs largely
taken by the author, grace the pages of this number. Many of
these pictures have never before been made public. Perhaps a
criticism might be made on the number of illustrations. For
example Fig. 4H illustrates nothing more then a tropical landscape
of which there are many in this number. This picture is labelled
Cacaofarm whereas tall palms are the more conspicuous. Fig. 4!)
does not illustrate anything different than the picture on the pre
ceding page. With the exception of repetition of type pictures no
material criticism is ventured.
This masterpiece of pharmacognosy will be of great value and
comfort to teachers of pharmacognosy, materia medica, and phar
macy, and to professional pharmacists, food and drug experts and
analysts, and to physicians. To be fully appreciated it must be
seen. J. 0. Schlotterheck.
Ghundlaoen u.ni> Ergebnisse deb Pplanzenchemie. Nach der
schwedischen Ausgabe bearbeitet von H. Euler, Professor der
Chemie an der Universitiit Stockholm. Erster Teil: Das
chemische Material der Pflanzen, Ein Bd., pp. , mit einer
Abbildung im Text. Verlag von Friedrich Vieweg und
Sohn, Braunschweig. 190N. Geb. M. 7.00.
While there has been no derth of good literature on such special
phytochemical subjects as the sugars, the alkaloids, the resins, the
volatile oils and even the ferments, the want of a general treatise
on plant chemistry has been universally felt ever since the old
standby of Hilger, Husemann and Hilger has been found wanting.
The work of Czapek, meritorious as it is in its way, has not filled
the gap. Czapek is a sort of biochemical Beilsteiu, good to have on
the shelves of the investigator, but it is not a treatise to be placed
into the hands of the average student. The title of Euler's work
certainly looks promising and if we learn from the preface that it is
but the first part of a larger work our hopes are increased.
The materia phytochemica which is disposed of in this part, is
to be followed by a treatise of the chemical and pl^sical laws in so
far as they are necessary to an understanding of the material
changes studied in the plant. While a complete biochemical system
.120 PHARMACEUTICAL REVIEW.
is not to be attempted, the life processes of the plant are to be

illustrated in a series of pictures as it were.
In the part that has just made its appearance, the author
acknowledges his indebtedness to Czapek for specific data, but
points out that the principal difference between the two works lies
not so much in the smaller size of the newer treatise, but in the
arrangement of the material. Whereas neither chemist'nor botanist
seem to be able to find any system in Czapek, the phytochemieal
material in Euler is arranged according to strictly chemical ideas of
classification.
The writer has long been interested in the logical classification
of chemical compounds and has had occasion to point out how the
organic chemist of the present generation as well as of the genera
tions just past, while no longer essentially a plant chemist as were
the earlier representatives of his class, has been unable in matters
of classification, to get away from plant chemistry. This is true
though he himself be unconscious of such a dependence on past
traditions. This unhappy state of affairs is even more conspicuous
in this treatise in which such classes of compounds as carbohydrates,
alkaloids, terpenes etc. are rightly emphasized. The anomaly to
which this attempt to blend two systems, based on totally different
principles, leads, is illustrated e. g. by omitting the hydrocarbons
entirely from the first part devoted to aliphatic compounds, and
placing heptane, a striking constituent of Pinus sabiniaim in an
appendix to the chapter on terpenes and camphors.
That, in the choice of plants selected to illustrate the occurrence
of specific substances, errors of judgment have crept in, will surprise
no one at all familiar with the vast amount of material to be sifted
for such a purpose.
Yet in spite of any and all defects that must attach to a work
of this kind, we welcome this attempt as a general treatise on plant
chemistry. It will prove of value particularly to the teacher of this
subject which for a time has been ignored rather than fostered by or
ganic chemists. Now that such a man as Emil Fischer has stated that
organic chemistry becomes of special interest only then when applied
to the problems of plant and animal life, others no doubt, will find
it fashionable to assist in working out some of the innumerable
problems remaining to he solved. Contributions of this sort will,
therefore, be appreciated not only by those who have in the past
heen true to plant chemistry, but to the organic chemist as well.
Let us hope that someone will translate this German translation
from the Swedish into English. E. K.
Volume 20. NOVEMBER, 1908. Number 10.
Deterioration of Some Standard Pharmaceuticals.*
IS.v H. B. Barnard,
According to the Pharmacopoeia, Ammonia Water is an

aqueous solution of ammonia containing 10% by weight of gaseous
ammonia. As made up the solution we prepared contained 11.7%
by weight of ammonia gas, corresponding to 111.7% U. S. P.
strength. This was divided into five portions and placed in bottles
under similar conditions as before described. At the end of two
weeks there was no change in the first four samples. The 5th sample
in the uncorked flask at this time, however, had deteriorated nearly
50% and now contained but 5.92% of gaseous ammonia. Two weeks
later it contained but 3.71% and at the end of two months but
1.33% corresponding to 13.3% U. S. P. At the end of three months
but 0.65% of ammonia gas was present, and at the end of
four months but 0.36% was there. At the end of the 5th
month the solution was but 2.3% U. S. P. and was not further
analyzed. At this time sample #1 was 108.4% U.S. P. representing
a deterioration of 3.3%. Samples #2 and 3 had likewise deteriorated
but little and were still well above pharmacopoeial requirements
Sample #4 which was kept in a bottle with a cork stopper, showed
no greater deterioration than the other samples up to the end of
the second month. At that time, however, it became difficult to
keep the cork stopper in the bottle, the action of the ammonia gas
on the cork producing a tendency to dry it out. Under these un
satisfactory conditions at the present time the ammonia shows
a rating of 93.8% U. S. P. Our results show that ammonia water
if kept in tightly stoppered glass bottles, no matter whether exposed
to the Hght or not, deteriorates but slightly upon standing. Our
figures also show that ammonia water kept in a close corked bottle
does not deteriorate rapidly. If, however, the container is not
stoppered, rapid deterioration takes place and in a short time ami
the solution becomes of no value for medicinal purposes.
* Continued from page 31 't.
(321)
AQUA AMMONIA
120 ! i ) 10 12 14 IS 1B 20 22 24 2
110
\
\ ..— -
100 \
\
I \
\
90 I
\
\
■0 \
\
70 \
\
\
10 \
\
\
SO \
\
40 \
\
\
\ LEG END
10 \
\
2
\ 3—
\ --
5-
10 \
•
The numbers O to 1 UO represent percentages 1". S. P.

The numbers '2 to 28 indicate we. ks.
The numbers of the legend, vl*. 1 to are thoHe of the |irci>arntlons mentioned
in the ext.
PllARMACEUTICAL REVIEW. 323
No one preparation causes the druggist more trouble than his

Lime Water. As prepared by the druggist it is made by sinking
ordinary commercial lime with the addition of water with occasional
agitation for an hour. After the suspended particles have subsided
the supernatant liquid is decanted and rejected. Distilled water is
then added to the residue and the mixture thoroughly shaken. This
process is repeated for several days and at length the liquid holding
the calcium hydroxide in suspension is poured in a glass stoppered
bottle. The solution we studied was made under these conditions
and at the time of preparation assayed 112.6'/' U. S. P. strength,
corresponding to 0.1536'/ of pure calcium hydroxide. This solution
was then divided into five portions under the same conditions as
l>efore recited. No precipitated lime, however, was allowed to remain
in any of the bottles, the solution being filtered before the samples
were prepared. A 6th sample was made according to the U. S. P.
directions, the excess of lime being left in a bottle which was shaken
between titrations, during the entire period. This sample was 113. 6'/ .
U. S. P. At the end of two weeks but little change was noted in
the first samples. Sample #5, however, showed a loss of 20'/
strength, and in the following two weeks showed a loss of 30'/. At
the end of six weeks it was 28.8'/ U. S. P. and at the end of two
months the clear solution was neutral to sulphuric acid and con
tained no calcium hydroxide. At this time the other samples were
still well above the pharmacopoeial requirements, although a loss of
from C> to 10'/ was evident in each case. Sample (*6 which con
tained undissolved lime was at this time of the same strength as
sample #2, viz. 107.3'/ 1'. S. P. At the end of 10 weeks, at which time
the solutions were exhausted, sample *1 showed 92.2'/, #2, 100.5'/,
S3, 92.6'/, #4, 93.6'/< and sample #5, 106.3'/. At the end of 28
weeks the strength of sample #6 has increased to 108.4'/ U. S. P.
From these results it is apparent that lime water properly prepared
and kept in a close stoppered bottle containing some undissolved
lime, will deteriorate very slowly and will preserve its strength at
least six months after preparation, a much longer time than is
usually necessary in the case of a dispensing druggist. A study
of the results obtained is interesting chiefly because of the fact that
it proves the ability of the druggist to make and keep in stock
standard pharmaceuticals which are commonly and erroneously
supposed to deteriorate rapidly. The results of the work with the
324. PHARMACEUTICAL REVIEW.
lime water and ammonia water appear to prove that the uniformlylow
grade of these products as dispensed, is due to carelessness in storage,
but on the contrary the study of tincture of iodine and spirits
of camphor shows this explanation to be not founded on fact, and
the druggist must offer some other explanation of the character of
these preparations. The results of these investigations are so posi
tive in character, so helpful to us in the enforcement of the Pure
Drug Law and have been received so cordially by the drug trade as
explaining hitherto little understood reactions, that we have started
another series of experiments which will, we hope, be completed
during the coming winter. We are now studying the rate of deterio
ration of tincture of ferric chlorid and sweet spirits of nitre. We
have undertaken to determine the rate of oxidation and volatiliza
tion of such essential oils as the oils of lemon, orange, gaultheria,
peppermint, turpentine, etc., questions of great importance to the
dispensing druggist and, as well, to the manufacturers of food pro
ducts. We believe that such work as this will establish the value of
food and drug control laboratories to the manufacturing and retail
trade, and that they will eventually be appreciated as instruments
designed to help and advance their interests instead of mere,
nccessories to legal prosecutions.
In closing I wish to express my appreciation of and to give full
credit for the careful analytical work of Mr. Ivy L. Miller of the
State Laboratory of Hygiene, without which this paper could not
have been prepared.
;i2c PHARMACEUTICAL REVIEW.
Coniferous Oils of the Northwest.*
By /. W. Brandel.
II. Needle Oil from Douglas Spruce.

By itaude Sweet.
The Douglas spruce, one of the most widely distributed trees of
North America, is also the most valuable inhabitant of the great
coniferous forests of the Northwest. It is the most commonly occur
ring tree throughout both the valleys and mountainous regions of
Washington.
The Douglas spruce or red fir is botanically :* Psendotsuga
mucronata, Sud worth; P. donglasii, Carriere; P. douglasii taxifolia.
Carriere; douglasii dcnudata, Carriere; P. lindeyana, Carriere:
taxifolia, Britton; P. douglasii, var. glauva. Mayr; P. taxifolia,
var. elongata, Lemmon ; Pinus taxifolia, Lambert: P. Douglasii.
D. Don.: P. canadensis, B. Hooker; P. douglasii, vur. taxifolia.
Antoine: P. douglasii, var. brevibracteata, Antoine; Abies taxi
folia, Poiret; A. mucronata, Rnfinesque; .1. mucronata, var.
palustris, Rafinesque; A. douglasii, Lindley; .1. douglasii, vnr.
taxifolia, Loudon; Picea douglassii, Link; Pkea douglassii, Bert-
rand; Tsuga douglasii, Carriere; T. douglasii fastigeata, Carriere;
T. lindleyana, Itoezl.
The. oil was obtained from small trees and underbrush identified
by Dr. T. C. Frye of the University of Washington.
Upou distillation with steam the fresh needles and twigs yielded
0.8 to 1 per cent of a greenish-yellow oil having n limonene-like odor.
Specific gravity at 23° C., 0.8680; a„ = —62.5°.
The oil contained no free acid. Saponification number = 80.C>.
which corresponds to 30.3', i borneol ncetate; acetylization number
= 92.1, which corresponds to 32.2% of borneol acetate or 25.3'/; of
free borneol in the original oil.
• Sargents' "yiva.
PHARMACEUTICAL REVIEW. :\>-i
The oil gave no test for aldehydes when treated with sodium
add sulphite.
The oil was fractionated with a one-half meter column into
fractions of 5° each and then refractionated. Fractions and volumes,
specific gravity, and «n are given in the following table:
Hollltig point. Volume. Sp. (?r. at 25° C. an at 25
-161° 14 c. c. 0.807 -74.9
161-162° 7.5 0.863 -76.1
102-103° 16 it 0.866 -76.1
163-164° 13 ti 0.867 -74.
164-10.-,° 15 0.868 -68.1
16.")—166° 9 0.868 -66.8
166—167° 31.5 .. 0 865 -69.8
167—169° 8 <i 0.872 -63 5
169-170° 5 it 0.872 —56.2
170-171° 5 .. 0.872 -55.3
172-175° 8 >< 0.873 -53.
175-177° 4 tt 0.874 -50.1
177-190° 9 tt 0.875 -39.4
190+ 24 •'
From the volumes of the various frac ions it can be seen that,
the oil consists largely of terpenes, the amount of oil above 175°
being comparatively very small.
Although the lower fraction had a decided terebinthinate odor,
no crystalline pinene nitroso-chloride was obtained.
Fraction 175—176° had n decided limonene odor but, undoubt
edly owing to the very small quantity of the fraction, no crystalline
tetrabromide could be obtained.
All the fractions from 161° to 169° were tested for camphene by
the following method.* The fraction was dissolved in an equal volume
of benzene and a solution of mercuric acetate added at ordinary
temperature. The separated compound was washed with water,
alcohol and ether until white. This compound was suspended in
water and hydrogen sulphide passed in for from four to five hours
with frequent shaking. The black compound was filtered off and
distilled with steam, when solid camphene passed over. The com
pound thus obtained was a crumbling, slightly crystalline sub
stance, with a faint odor of camphor and melted at 47°.
* Ber., !15, p. 2995.
Fractions and 102° yielded large quantities of camphene;

eaeh succeeding fraction yielded less until, at 169°. there was very
little.
The residual oil (24 c. c.) was saponified and distilled. The
greatest amount came over between 180° and 20.r>o. The higher
portion was a deep green oil.
The entire saponified oil, the amount of which was too small to
fractionate, was tested for borneol as follows: 100 c. c. of nitric
acid, sp. gr. 1.0403, was cooled while the oil was gradually added.
A crystalline substance which dissolved in alcohol and was pre
cipitated by water was formed.
After purifying by reprecipitating from alcohol, the substance
melted at 171°. The substance had the physical properties of
camphor and was identified further by the formation of an oxime.
The oxime, which was precipitated by water, was recrystallized from
alcohol and melted at 113°. This is lower than the true melting
point 118°— 119°, but the amount of substance was too small to
purify further.
The examination of a larger quantity of oil is now in progress.
University of Washington.
Thymoquinone and Hydrothymoquinone.

From the laboratory of Etl\\;ml Krrmers.
Introduction.
This revision. as it were, of the chemistry of hydrothymoquinone
and thymoquinone has grown out of the phytochemical study of
Monarda begun in this laboratory more than ten years ago. Among
the volatile constituents of the representatives of this species, cymene
and a number of its oxidation products play an important role, in
that they contribute not only to the aroma of the plants, but to
the color effects of flowers and stems as well. Moreover, the signifi
cance of these substances is by no means restricted to the genus
Monarda.
The constitution of the substances referred to and their relation
to each other can best be expressed by their structural formulas
which are herewith reproduced.
CHs
c
HC COH
I
I
HC CH
CHs ., CHa CH«
I ■; I
u I C C
CH
CH HC COH HC \C=0
I I*II
Vll3 CH..,
HC /CH Curvacrol HOC CH 0--C CH
C CHa C C
I J. I !
CH C CH CH
\ HC CH
CHa CH3 i CHs CH:: CHs CHa
(ymene jj^' COH Hydro- '1 hyuioqulnone
t hyuioqulnone
C
in
CHs CHs
Thymol
In addition to these
OH
<H:I CHs
OH, CHs
Thymoqulnhydrone
has also been isolated.* The metallic derivatives of thymo'quiu-
hydrone, no doubt, exist in these plants, as do in all probability
the phenoquinone8 of thymoquinone with thymol, or carvacrol, or
both. Resides these, hydroxythymoquinone or other oxidation pro-
duets and the polymerof thymoquinone may be expected to be present .
With these substances isolated, the further study of the Mona r-
das along this line would seem to offer little attraction. Such, how
ever, is not the case. As a matter of fact, the phytochemical study
of this group of compounds, even if restricted to the Monardas, has
but scarcely begun, as even a crude treatment of the oils shows.
The mere separation of the volatile oils into their phenol and non-
phenol components is connected with the formation of byproducts
which, while they annoy the chemist, may well tempt him to further
work.
Recognizing^the necessity of a more perfect knowledge of these
substances for the phytochemical studies indicated above, a revision
of their chemical literature was begun some years ago. As the first
fruits of this revision, the studies of nitrosothymol t and of nitroBocar-
vacroli were published. As a second step, the reduction products of
these nitroso compounds, amido thymol and nmido carvacrol, arc
now being studied in this laboratory. The study of hydrothymo-
quinone and thymoquinone was assigned to Miss Wakeman. Of
especial interest in this connection are the effect of oxidizing agents,
including vegetable oxydases, also of sodium and potassium
hydroxide (used in the separation of the phenols) and the action of
light in bringing about polymerization as well as autoxidation.
* The formula admitH of several structural conceptionH,
%t Phar. Archives,
Ph. Rev., •>•!, p. +.148.
p. 170.
The details of the experimental work, in so far as they seemed

to call for separate treatment, are herewith given. The revision of
thymoquinone. hydrothymoquinone etc. follow as separate chapters.
Experimental Part.
By Xclllc Wukeman.
Preparation and purification of hydrothymoquinone.
Hydrothymoquinone was prepared by grinding thymoquinone in a
mortar to as fine a powder as possible, suspending this powder in
water and passing a current of SOa through until saturated. The
black quinhydrone is formed in a short time and if allowed to stand
for a few days, with frequent agitation, is completely changed to
hydrothymoquinone. The reduction takes place more quickly and a
purer product is obtained when a small amount of thymoquinone
in a comparatively large volume of water is used, viz. 10 grams
thymoquinone to 500 c. c. of water.
This product, which is of a dirty white color, if allowed to stand
will revert to t'uymoquinhydrone, and, ultimately, to thymoquinone.
For the purpose of purification it is dissolved in boiling water,
filtered and allowed to crystallize. This product is again dissolved
in boiling water containing a little sulphurous acid, filtered and
allowed to crystallize. Glistening white crystals made up of short
cubical priBms and flat four sided plates are thus obtained. Melting.
point, 140°. Soluble in hot water, alcohol, ether, and glacial
acetic acid. Insoluble in cold water, limonene, benzene and hexnne.
In ammonia it dissolves producing a red liquid.
Exposure of thymoquinone to light. A solution of ten
grams of thymoquinone in 50 c. c. of alcohol was exposed to the
light for several days. In a few hours the solution became colored
a deep red, showing the reduction of thymoquinhydrone. In a few
days a white precipitate of hydrothymoquinone was obtained. After
long standing the solution lost much of its color. The amount of
alcohol used, however, 'was relatively large so that much of the
hydrothymoquinone remained in solution. This experiment was per
formed during a season of prolonged cloudy weather, therefore, no
account was taken of the rate of reduction.
Solutions of thymoquinone that had stood in diffused daylight,
on the laboratory shelves, for several years were noticed to have
become completely decolorized, while in the bottom of the bottles
there' was a white precipitate of hydrothymuquinone. To test the

dependence of this reaction upon the action of light, and to deter
mine the time factor, 2%, 5% and 20'/; solutions of thymoquinone
in limonene were made in duplicate. One bottle of each solution
was carefully kept away from the light, while the other was exposed
to bright sunlight and the length of exposure noted. After one
hour's exposure a decided darkening of all three solutions was ob
served. After six hours exposure all three solutions had taken on a
brown color, varying in intensity with the strength of the solution,
while those not exposed to light had not changed perceptibly. Here,
again, the cloudy weather interfered with the experimental work and
the solutions were exposed only twenty-two hours out of thirty
days. At the end of this time the solutions retained their dark
color, showing the formation of thymoquinhydrone, but no hydro
thymoquinone was precipitated. The solutions not exposed to light
had not changed in appearance.
Preparation of quinhydrones. Thymoquinhydrone was
prepared by dissolving molecular quantities of thymoquinone and
hydrothymoquinone in alcohol, mixing the solutions and allowing
them to evaporate spontaneously. A shining violet black crystalline
product was obtained. This is a very unstable substance and in a
few days a yellow powder of thymoquinone could be seen on the
edges of the crystals, caused by the oxygen of the air.
By mixing ethereal or alcoholic solutions of hydrothymoquinone
with quinone, a quinhydrone deep red in color is obtained on eva
porating the solvents. When mixed in aqueous solution, however,
thymoquinone is immediately precipitated.
By mixing ethereal or alcoholic solutions of thymoquinone and
hydroquinone, upon evaporation, a deep blue compound changing
to reddish brown is obtained.
Preparation of thymoquinone from liydrothymoquin
one by oxidation with KaCra07. Thymoquinone was prepared
by dissolving 10 grams of thymol in 20 grams of sulphuric acid and,
when cool, adding, slowly, never letting the mixture get hotter than
the hand can bear, a solution of 10 grams of potassium dichromate
in about 300 c. c. of water and diluting to about 500 c. c., then
distilling with steam.
This is a very easy and rapid method of preparing small quan
PHARMACEVTICAL REVIEW. 333
.A
tities of thymoquinone, but it was found to be very wasteful since
the yield was never more than 20% or 25'/r nnd, when larger
quantities were used, generally less.
Preparation of thymoquinone through nitroso thymol
and amido thymol. A modification of the method of Lieber-
maim and Ilinski was next tried and, after repeated trials to secure
correct proportions and proper conditions, a method was devised
by which a pure product and a yield of from 90' < to 93% could he
obtained. The several steps of the reactions involved can best ht'
expressed by a series of formulas:
CioHisOH > CioIIu(OH)NO > C10Ili2(OH)NHa

Thymol "NltroHothyuiol" Amhlothymol
> CioHn(OH)N:NOH > CioHia(OH)» > CViHigO2
Dlazothymol Hydrothymoqulnonc Thymoqulnonc
Nitroso thymol was prepared according to the directions of

Kremers and Brandel (1902), making a few minor changes in pro
portions and methods of handling. The modified process is given
in full detail.
Dissolve 5 grams of thymol in 25 c. c. of 95 p. c. alcohol and add
25 c. c. of concentrated hydrochloric acid. Place this solution in a freezing
mixture and add gradually, with constant stirring, crystals of sodium
nitrite till 5 grams have been added. The solution at first becomes light.
green, then dark green, and, after a few minutes, solidifies to a bluish mass.
Transfer this to a beaker containing about a liter of cold water and stir
until the product becomes light yellow and fluffy in appearance. Wash this
product with cold water and use it for the preparation of thymoquinone
while still moist. Yield of nitroso thymol about 6 grams.
It is very necessary that the bluish mass be added to a correspondingly
large volume of cold water and stirred till soft and light, and pale yellow
in color, especially when large quantities (50 grams or more) of thymol
are used; otherwise brownish lumps will form that will not go into solu
tion and the yield of thymoquinone will be materially lessened. A soft,
pale yellow nitroso compound means almost invariably a good yield of
thymoquinone.
Dissolve the nitroso compound in about 300 c. c. of 10 p. c. ammonia,
with constant stirring, allowing each part to dissolve before more is added.
Filter and pass in sulphuretted hydrogen until the amido compound is all
precipitated. Filter rapidly on a force filter, keeping a layer of water
above the precipitate while filtering and washing to prevent oxidation by
contact with the air.
Dissolve the amitlo compound quickly in an excess of 5 p. c. sulphuric

ncid (about 200 c. c.). Add gradually crystals of sodium nitrite till about
8 grams have been added shaking vigorously after each addition. Heat
on a water bath, to about 60°, shaking occasionally till most of the gas
has passed off. Distil with steam and separate out the thymoquinone.
It requires several hours to prepare thymoquinone by this
method. When necessary to allow it to stand over night, it was
found that the best results were obtained by leaving it either in the
ammonia solution or just before distilling, after adding the sodium
nitrite. If proper precautions are observed an excellent yield and a
pure product are obtained. Melting point 45°. Soluble in hot water,
alcohol, ether, chloroform, benzene, limonene, hexane, kerosene. The
crystals are lemon yellow in color, and constitute flat, four sided
pKtes.
Polymerizing action of light upon the quinones. To
test the effect of light on thymoquinone and hydrothymoquinone,
and to determine the rate of action, duplicate solutions of }£ gram
of each thymoquinone, hydrothymoquinone, quinone, and hydro-
quinone in 50 grams of anhydrous ether were made. By placing in
a porcelain crucible top 5 drops of a quinone and adding to it 5
drops of its corresponding hydroquinone the quinhydrone reaction
was obtained. One bottle of each solution was set in bright sun
light while the other was kept away from light. At the end of one
hour's exposure the solutions were tested for the quinhydrone
reaction. The quinone treated with hydroquinone responded quickly :
but no blue color at all was produced with the thymoquinone and
hydrothymoquinone. The solutions not exposed to light reacted as
before, as did also the hydroquinones when treated with unexposed
i|uinones. After an additional hour's exposure the quinone no longer
ga ve the quinhydrone renction when treated with hydroquinone, and
the brownish color produced between thymoquinone and hydrothy
moquinone was much lighter. Other reactions as before. After six
hours exposure the solutions ceased to give the brownish reaction
when treated with their respective hydroquinones, while the solutions
not exposed still retained their capacity for reaction.
Further exposure caused no change in the color of the product
obtained by treating the quinones with hydroquinone, faint yellowish
in the case of thymoquinone and brownish in that of the ordinary
quinone. The solution of ordinary quinone had changed to more of
a brownish color, lighter however, and the thymoquinoue solution

was of a much lighter yellow than before exposure. At the end of
six weeks there seemed to be no change in any of the unexposed
solutions, or in the exposed solutions of the hydroqninones.
BIBLIOGRAPHY.
Lallemand, A. 1853.
Sur la composition de l'essence de thym.
('. r. 38, p. 1022 (Annalen, 101, p. 129).
Lallemand, A. 1854.
Note sur une classe de combinaisons homologues des quinoile et
de ses derives.
I', r. 37, p. 498 (Annalen, 101, p. 119).
"Thymoilol," i. e. hydrotuymoquinone, is obtained by the reduction of
"lhymoil" (thymoquinoue) by means of sulphurous acid, "thymoid" (thy-
moquinhydrone) resulting as the intermediate product (p. 121).
Lallemand, A. 1857.
Ktudes sur l'essence de thym.
Ann. Chim. Phys. [3], 49, p. 148 [Annalen 102, p. 119].
A study of thymol, thymosulphonic acid, "acide sulfoceto thymique"
ilinitrothymol, trinitrothymol, thymol sodium, thymene, trichlorthymol,
pentachlorthymol, thymoquinoue (p. 163), hydrothymoquinone (p. 164),
I hymoquinone amide ('.'), "acide thymoilique," hydroxy thymoquirione.
Kekule, F. A. 1867.
1-ehrbuch der organischen Chemie, Bd. , p. 399.
Criticism of Lallemand's formula for thymoquinoue.
A study of "thymoil,'' ' thymoilol," and "thymoid" giving properties.
Carstanjen, E. 1871.
J. pr. Ch., Ill, p. 50.
A review of the earlier work of Lallemand (preparation, properties,
ptc.), resulting in a correction of the empirical formulas of hydrothymoqui
none and thymoquinone. Also a discussion of the constitution of the com
pounds and of hydroxythymoquiuone.
Sigel, Otto. 1873.
ITeber die Bestandtheile des Arnica-Wassers und des iitherischen
A rnicaols.
Annalen, 170, p. 343.
The nonphenol fraction of the oil yielded hydrothymoquinone (m. pi 139
to 140° and elementary analysis) and methyl iodid; when heated with
hydriodic acid in sealed tubes.
Cars t anj en, E. 1877.

Zur Kenntniss der Chinone.
J. pr. Chem., 123, p. 410.
By oxidizing cymophenol (earvacrol) with H2SOt and MuOa, he obtained
''cymophenol? chinon'' which he identified with thymoquinone.
Armstrong:, H. E. 1877.
Ber. d. D. Chem. Gesell., 10, p. 297.
Monoamido thymol distilled with ferric chloride yields thymoquinone.
Llebermann, C. 1877.
Polythymoquiuone obtained by long exposure to light of an ethereal
solution of thymoquinone.
Andersen, M. 1881.
Ueber thymochinochlorimid.
J, pr. Chem., 131, p. 172.
Thymoquinone obtained by the action of calciumhypobromite on para-
amidothymol.
Llebermann, C. 1885.
Thymoquinone prepared by oxidizing nitroso thymol with KaCraOr.
Polythymoquinone distributed on the inner surface of a large flask.
Rychler, M. A. 1892.
Bull. Soc. Chim. (3), 7, p. 24.
Thymoquinone prepared by dissolving earvacrol in an excess of H2SOt
adding a solution of K2O2O- in excess and distilling with steam.
Valenr, A. 1897.
C. r., 125, p. 873. [Chem. Soc. Jr., 74, p. 420.]
A summary of the thermochemical data for the various quinones and
hydroquinones. The difference in the heat of formation between a quinone
and its corresponding phenol appears to be about 6 Cal ; for example,
Thymol = 76 Cal., Thymoquinone = 82.4 Cal.
OHveri-Tortoricl, R. 1897.
Gazetta, Chim. Ital., 27, p. 587. [Chem. Soc. Jr., 74, AI,
p. 304.]
Thymoquinone treated with chlorine yields a mixture of mono- and di-
chlorthymoquinones which could not well be separated.
Biltris, A. 1898.
Chem. Soc. J., 70, p. 199. [Chem. Centrlbl., 68, p. 887.]
Thymoquinone obtained by mixing lukewarm aqueous solutions of
hydrothymoquinone and quinone.
Ciamician and Silber. 1901.

Atti della reale Academia dei Lincei (S) 10, p. 90. [Chem.
Central bl., 72, p. 770; J. C. 8., 80, p. 329.]
The carbonyl group of aldehydes (benzaldehyde etc.), ketones (benzo-
phenone), esters, dikeUmes (qui none, thymoquinone) is reduced to an alco
hol group by light in the presence of alcohols (ethyl alcohol etc.) which in
turn are oxidized to aldehydes or ketones.
Brandel and Krenters. 1901.
Thymoquinone in wild bergamot oil.
Pharm. Rev.. 19, p. 200. [Chem. Centra lbl., 72, p. 1007.]
Discovery and identification of thymoquinone in volatile oil of Monaida
fistulosa.
Brandel and Krentiers. 1901.
Hydrothymoquinone in wild bergamot oil.
Pharm. Uev., 19, p. 244. [Chem. Centralbl., 72, p. 1007.]
Discovery and identification of hydrothymoquinone in the volatile oil
distilled from Monartla fistulosa. Like thymoquinone it had been previously
prepared artificially but had never before been isolated from a volatile oil
or otherwise found in nature.
Brandel and Kremers. 1902.
Nitroso Thymol.
Phar. Archives, 4, p. 170.
A study of the history, preparation and properties of nitroso thymol.
Kremers and Brandel. 1904.
Nitroso Carvacrol.
Ph. Rev., 22, p. 148.
A Btudy of the history, preparation and properties of nitroso carvacrol.
Brandel, I. W. 1904.
Ph. Rev., 32, p. 153.
The volatile oil from Monarda citriodora.
Hydrothymoquinone present uud the presence of thymoquinone indicated
in oil of Monarda citriodora.
Rabak, F. 1904.
Oxidase from Mouarda fistulosa.
Ph. Rev., 22, p. 190.
Directions for preparing an oxidase from the leaves and an account of
its use as an oxidizing agent in oxidizing hydrothymoquinone to thymo
quinone.
388 PHA RMACEUTICAL RE VIEW.
Phytochemistry in America II.*
Henry Trimble, the son of Stephen M. Trimble, a meinher of

the Society of Friends, was born near Chester, Pa., May 22, 1853.
He obtained his early education at the West town Boarding School
and at the age of 19 was ap
prenticed to learn the drug and
apothecary business. Two years
later, in 1814, he entered the
Philadelphia College of Pharmacy
from which he was graduated
with the class of 1876, his thesis
being "Benzoic acid as an anti
septic." After graduation he en
tered the University of Pennsyl
vania as a special student in
chemistry, mineralogy and bot
any. Here he remained for two
years, acting during the second
as lecture assistant to Professor
Sad tier who then held the chair of
General and Organic Chemistry.
In 1878 he established himself
in the drug business, associated
as partner with his classmate C.
W. Warrington. In 1879 when
Prof. Sadtler became Director of the chemical laboratory of the
College of Pharmacy its active supervision was given to Henry
Trimble, who, in 1883, having retired from the drug business, was
given the full rank of Professor of Analytical Chemistry, succeeding
Dr. Frederick B. Power in this position.
From this time on his energies were given to experimental and
literary work along the lines of pharmacy and chemistry.
m
* Contributed from the Seminary in Plant Chemistry at the University of Wis
consin by Nellie A. Hakeiaan and read by title before the Historical Section of the
A. Ph. A. at Hot Springs.
PHARMACEUTICAL REVIEW.. 339
His love for plant life especially fitted him for the study of plant"
chemistry and with his advanced students he carried out many original
investigations in proximate plant analysis. As early as 1890 he be.
gan to make a special study of the tannins, being incited thereto
by some investigations he had made into the methods of manu
facturing extracts from dye woods. As a result, in 1892, he pub
lished the first volume of "The Tannins",* a work which at once
took rank as an authority on the subject. He followed this in 1894
by the second volume, and at the time of his death had a large
amount of unpublished material intended for a continuation of the
series.
In 188.") appeared a small "Handbook of Analytical Chemistry",t
which ran through several editions and was then merged into the
Text Book of Pharmaceutical and Medical Chemistry, by Sadtler and
Trimble.t
His numerous contributions appeared principally in the American
Journal of Pharmacy, of which he became editor in 1894, and in
Garden and Forest, a horticultural publication. His untimely death,
August 24th, 1898, cut short his useful career at the age of
forty-five.
His phytochemical contributions are arranged chronologically in
the following list. A complete list of his papers with further bio
graphical detail will be found in the American Journal of Pharmacy
for Nov. 1898, vol. 70, p. 537.
1885. What is the chemical relation, if any, between the oils of peppermint
and spearmint. Am. Jr. Ph., 57, p. 484.
A chemical examination of Polygonum bjdropiper (jointly with
H. J. Schuhard). Am. Jr. Ph., 57, p. 21.
An examination of burdock fruit (jointly with P. D. McFarland).
Am. Jr. Ph., 57, p. 127.
1886. Analysis of Ariatolocbia foetida (Verba .del Iudio) (jointly with
S. S. Jones). Am. Jr. Ph., 58, p. 113.
An analysis of the under-ground portion of Phlox carolina. Am. Jr.
Ph., 58, p. 479.
1887. Tannin, its present and future sources. Franklin Inst. Journ., 123,
p. 442.
* Pubhshed bv J. B. Llpplncott Co., vol. I in 1892; vol. II in 189+.
t Published by P. Blacklston's Son * Co. lst ed. 1885; 2nd ed. 1886; 3rd ed.
1889; 4th ed. 1892.
t Published by J. B. Llpplncott Co. 1st ed. 1895; 2nd ed., 2 vols., 1898, now
Sadtler and Coblentz.
1888. The bitter principle of burdock fruit. Am. Jr. Ph., 60, p. 79.
Catechu aud gambier. Am. Jr. Ph., 60, p. 497.
Some Indiau food plants. I. Shepherdia argentea, Nuttall. Am. Jr.
Ph., 60, p. 593.
On the occurrence of solid hydrocarbons in plants (jointly with
Helen C. De S. Abbott). Am. Jr. Ph., 60, p. 321.
1889. Canaigre. Am. Jr. Ph., 61, p. 395.
Some Indian food plants. II. Lewisisa rediviva, Pursh. Am. Jr.
Ph., 61, p. 4.
Some Indian food plants. HI. Peucedanum eurycarpum, Coulter and
Rose. Am. Jr. Ph., 61, p. 4.
On a crystalline compound in Fabiana imbricata (jointly with H. J.
M. Schroeter). Am. Jr. Ph., 61, p. 273.
Oil of camphor (jointly with H. J. M. Schroeter). Am. Jr. Ph., 61,
p. 273.
The oils of wintergreen and birch (jointly with H. J. M. Schroeter).
Am. Jr. Ph., 61, p. 398.
An old sample of camphor oil (jointly with H. J. M. Schroeter).
Am. Jr. Ph., 61, p. 333.
1890. Eupa.torium purpureum. Am. Jr. Ph., 62, p. 73.
Some Indian food plants. IV. Peucedanum canbyi, Coulter and
RoBe. Am. Jr. Ph., 62, p. 281.
Some Indian food plants. V. California soap plant. Chlorogalum
pomeridianum, Knuth. Am. Jr. Ph., 62, p. 598.
Some American (ialls. Am. Jr. Ph., 62, p. 563.
The oils of wintergreen and birch (jointly with H. J. M. Schroeter).
Am. Jr. Ph., 02, p. 9.
1891. Geranium maculatum (jointly with J. C. Peacock). Am. Jr. Ph., 63,
p. 265.
Some Indian food plants. VI. The Yamp. Carum gairdneri,
Bentham and Hooker. Am. Jr. Ph., 63, p. 520.
1892. Purshia tndeutata, D. C. Am. Jr. Ph., 64, p. 69.
Chestnut bark tannin. Franklin Inst. Journ. 133, p. 407.
1893. Canaigre tannin (jointly with J. C. Peacock). Am. Jr. Ph., 65,
p. 101.
A proximate principle from Phytolacca decandvn. Am. Jr. Ph., 65,
p. 273.
The preparation of the oak tannin, with special reference to the use
of acetone as a solvent (jointly with J. C. Peacock). Am. Jr.
Ph., 65, p. 435.
1894. Four oak barks from India. Am. Jr. Ph., 66, p. 299.
1895. Report on tannin from an exudation of Pterocarpus draco, Liun£
and known in Jamaica as dragon's blood. Am. Jr. Ph., 67, p. 516.
The oils of wintergreen and birch. Am. Jr. Ph.. 67, p. 560.
On the tanning properties of the bark of three North American trees.
Garden and Forest. 8, p. 21)3.
1896. A contribution to the knowledge of some North American conferee
(jointly with 10. S. Bastin). Am. Jr. Ph., 68, pp. 21, 65, 136,
199, 242, 321, 383, 409, 554, 642; and 69, p. p. 90, 354.
The tannin of some acorns. Am. Jr. Ph., 68, pp. 601, 634.
Recent literature on the soja bean. Am. Jr. Ph., 68, pp. 309, 350.
Salt aud sugar in Waebingtonia filamentosa. Garden and
Forest. 9, p. 133.
Tannin value of North American trees. Garden and Forest. 19, p. 162.
Tannins of the palmetto. Garden and Forest. 9, p. 182.
1897. On the occurrence of strontium in plants. Am. Jr. Ph., 69,
pp. 296, 327.
The Tannin of Castanopais. Am. Jr. Ph., 68, p. 406.
The Tannin of Ceriops cauilolleana. Am. Jr. Ph., 69, p. 505.
The soy bean. Am. Jr. Ph., 69, p. 584.
The willow oak. Am. Jr. Ph., 69, p. 617.
Pomegranate rind. Am. Jr. Ph., 69, p. 634.
Source of abietene. Garden and Forest. 10, p. 202.
Recent advances in the study of the resins. Franklin Inst. Jr., 143,
p. 178.
1898. An exudation from Larix occidentalis. Am. Jr. Ph , 70, p. 152.
H42 PHARMACEUTICAL REVIEW.
The Apothecary, A Literary Study.
By Edward Kremerx.
IV. Beschreibuna; aller Staende anf Erden.

"Die Beschreibung aller Staende auf Erden,"* is of a peculiar
interest to the student of the apothecary in literature because of the
wood cuts by Jobst Amman. That of the apothecary e. g. has been
utilized even in recent years as copy for the book plate of the
apothecary Herman Gelder by Lor. R. Rheude; and still more re
cently as a design for a programme of a pharmaceutical students
society.
Its pages receive an added charm from the verses by Hans
Sachs, the folk poet of Nuernberg, that quaint German city on the
Pegnitz which has contributed so many men who have added to the
fame of German art and letters during the time of her greatness
before the thirty years' war.
It is not the intention of the writer to review even briefly the
glories of Niirnberg where l6th century grandeur is admired even
today by the foreign traveler. All that is to be attempted in this
brief account is to present to the reader a few specimens of the art
of Jobst Amman with the rhymes by Hans Sachs.
Naturally the writer has selected those characters which will aid
in a better understanding of the apothecary, viz. the physician,
the dentist, the barber, the cupper. The respective cuts are largely
selfexplanatory and call for little other comment than that supplied
by the Niirnberg poet.
• Eycentllche Beschrelbung Aller Stiinde auff Erden. Hoher und Nldrlfrer. Gelst-
llcher und Weltllcber, Aller Kiinsten, Hand wercken und Hiindeln u. Vom groessten
bis eum kleinesten. Aueh von lrem rrsprung, Ertindung und fjebriiuchen. Durch den
weitherumpten HauH Siwhsen gantz fiel*slg beschrieben und In Teutsche Reimeu
gefasset. Sehr uutzbarllch und lustig zn lesen, und auch mlt kuenstrelehen Flguren
deren gletchen zuvor niemads eesehen. alien Ktaenden, Bo in dleaem Bnch begriffen, au
ehren und wolgcfallen, Allen Kiinstlern aber, nlB Malern, Goldschrolden u. »u son-
derllcbem dienst in Druck verfettlgt. Mlt Rornlscher Keyserlieher Meyestet Freyheit,
Gedruekt zu Franckfurt am Mnyn
On the last page: Gedruekt ,'zu Franckfurt am Mayn, durch Paulum Keffelern.
In verlegung Slgmuudwas
The first edition Feyerabends. 1574. Raben aud published in l.ri68.
printed by Georg
PHARMACEUTICAL REVIEW. 34.'1
To the average reader who may uot have beard of Jobst Amman
or his work, and possibly little more of the rhymster than Ihot
"Hans Sachs war ein Schuh-
macher und Poet dazu"
a few explanatory words may not be entirely unwelcome.
Among the German engravers of the second half of the sixteenth
century, Jobst (Jodocus) Amman occupies a very prominent posi
tion. He was born in Ziirich, but of his apprenticeship and training
nothing definite is known. In 1560 he came to Nurnberg where he
died in 1591. His principal activity dates from 1564 whea he began
to work for Sigmund Feyerabend, a well known publisher of Frank
furt. It is said of Amman that he followed life, i. e. was more
realistic, than any of his contemporaries. This much at least is
certain that his output was wellnigh increditably great and that
the editions of works with his cuts followed each other in rapid
succession. Even to-day one can enjoy the naturalness of the
characters and the humor to which the artist has given expression,
as well as the technical skill hi the execution. Amman's peculiar
field was his own time and generation. His deliniation of the apo
thecary and related characters are, therefore, of special interest to us.
Second only to the wood cuts are the rhyme supplied by the
people's poet of Nurnberg. Hans Sachs was born 1494 in Nurnberg
as the son of a tailor! He attended the Latin school and was
apprenticed to a shoemaker. At the same time he acquired the
rudimentn of the "Meistergesang". After five years of "Wander-
schaft," during which he visited the principal cities of Germany while
perfecting himself in his trade, he returned to his native city and
settled down as a shoemaker. He died in 1576 as a well-to-do and
highly respected citizen.
Everything that Hans Sachs experienced or read was uncon-
siously turned into rhyms. This was done without affectation or
attempt at art, but with a naive grace and vivid conception that is
not without its charm even to-day. Of the fllthiners, so characteristic
of his time, he is as free as but few.
The photographic reproductions, which constitute the principal
feature of this brief account, speak for themselves. This list of
characters, depicted by Amman, may prove interesting for several
reasons and is here given.
1. Der Bapst. 47. Der Sch wartzferber.
2. Cardinal. 48. " Weber.
3. " Bischoff. • 49. tt H iiter.
4. Die Pfafien. 50. ti Schuhmaoher.
5. " Monch. 51. tt Balbierer.
6. " Jacobsbriider. 52. tt Zanbrecher.
7. Der Knyser. 53. II Bader.
8. " Konig. r>4. it Glockengiesser.
9. " Fiirst. 55. U Fingerhuter.
10. " Gentelon. 56. Liiderer.
11. " Doctor. 57. Brillenmacher.
12. " Apotecker. 58. it Biiratenbinder.
13. " AstrouomuB. 59. t• Kammacher.
14. " Procurator. 60. it Tchuchscharer.
15. " Schrifftgiwser. 61. ti Schlo8Bcr.
16. " Reis«er. 62. ti Circkelschmidt.
17. " Formschueider. 63. it Messerschmidt.
18. " Papierer. 64. tt Sporer.
19. " Buohdriicker. 65. it KupferHchmidt.
20. " Bricffinater. 66. tt Buechsenschmidt..
21. " Bnchbtnder. 67. >i Uhrmacher.
23. " Handmaler. 68. II Kotschmidt.
23. " Gluser. 69. it Nailer.
24. " Glnsmaler. 70. ii Sensenschmidt.
25. " Seydenstieker. 71. •> Blatner.
26. " Goldtschmid. 72. ii Huffschmidt.
27. " Steiuechneider. 73. it Beck*chlager.
28. " Bildhauwer. 74. II Schellenmacher.
29. " KaufTmauti. 75. Kandelgiesser.
30. " Jiid. 76. " N'adler.
31. " Miiutzmeister. 77. Pauzermacher.
32. " Goldtschlager. 78. tt Pogner.
33. " Kramer. 79. tt Waegleinmacher.
34. " Beutler. 80. Lateramacher.
35. " Giirtler. 81. n Sattler.
36. " Nestler. 82. ti Haffner.
37. " Metzger. 83. it Spiegler.
38. " .lager. 84. II Schleisser.
39. " Koch. 85. II Steinmetz.
40. " Miiller. 86. II Ziegler.
41. " Beck. 87. II Zimmerman n.
42. " Bauwer. 88. tt Schreiner.
43. " Bierbreuwer. 89. II Wagner.
44. " Woydmaun. 90. II Buetner.
45. " Schneider. 91. II Holzdrechssler.
46. " Kurschner. 92. It Buechsenschaeffter.
93. Der Permennter. 104. Die Singer.
94. " Sieber. 105. Der Organist.
95. " Seyler. 106. Drey Pfeiffer.
96. " Seh iffunvu n . 107. •' Geiger.
97. " Fischer. 108. Harpffeu mid Lnuten.
98. " Hefftelmacher. 109. Heertrummel.
99. " Kebinaiui. 110. Der IVppichmacber.
100. " Bergkuapp. 111. " Geltnarr.
101. " Drataieher. 112. " Fressend Sarr.
102. " Olmacher. 113. " Schalksnarr.
103. " Lautenmacher. 114. " Stocknarr.
From the ahove list it becomes apparent that the physician

(No. 11) follows, almost immediately, the representations of the
spiritual kingdom and the worldly potentates; also that the apo
thecary immediately follows the physician. The physician is re
presented as diagnosing the urine of the patient who has come to
seek his professional aid; the apothecary as engaged in the act of
reducing a drug to powder in a mortar. While the physician, with
his professional robe, is decidedly the more dignified of the two,
there is something about the apothecary and his surroundings that
is indicative of real life. The second cut, at the same time, affords us
a glimpse of a sixteenth century apothecary shop: the space is but
small, for the city surrounded by a wall was naturally crowded and
did not admit of the luxury of large stores; the containers on the
shelves reveal their mysterious labels; the jars are evidently covered
with bladder or paper; the sugar pyramids occupy a prominent
position; near the ceiling are suspended strings of animal or vegi-
table drugs; a few implements are seen in the rear. As yet there is
no luxury of tiled floor or fayence containers, but the shop, like the
customers, indicates humble conditions rather than the riches grow
ing out of the proverbial ninety-nine per cent, profit of the apothecary,
.'!46 PHARMACEUTICAL REVIEW.
2W& Wit cm 5)ertor UrKvWtyl

3Cn torn S)axn tan t'dj fchcn fitp/
qBatSvandfyit ct'n Sftcnfcljn tfiuf fcfabn/
£kmf<m tA fccfffcn m it &om i25nal>cn/
3)urdjcm(5propotorCXc«ptf
SDoafctner ftrancffycii tritorffrc&f.
JDap Ocr SKcnfc^ wi&c r wc rt> scfunl>/
2foiMK3r&n<pcrfunt>.
Fig. 11. The Physician.

2fc$ in mctticr 3fpofc(fn

Ôtrf #?atcrp Dic lic&lidj fcfctwtf«/
gutfar mit ^Birtf<n ic$ confute .
dftarfe aucfc purga^cn »nt> &ifticr/
&uc$ ju (?<r<fcn Dcn frantf«i fcfct»adj«
Slan idj manc&crfcp Xa&ung macfyn/
affce ttacfc tor £r r«§f
Fig. 12. The Apothecary.

3$ Mtricruflffrt aUtntfydbm
San m.i<%n w'd getffatncr ©al&ttf
trijty ûn&cn iu fccpfn mtt ©naDcn/
>crg(ctd^ «2&ctn^rflc^ t>nt>a(t<5djaton/
grt*i*ofcn fccpfn/Dcn (Sfarcn ffedjn/
;QcnQ3ran&t fcfefccn tmt> gdn aupforccfytf
3i>crl<#n
Fig. 51. The Barber.

Literary.
Incompatibilities in Prescriptions. By Edsel A. Ruddiman,

Third Edition, 312 p. Published by John Wiley & Sons,
New York.
The difference between the second and third edition might be
easily overlooked by a casual observer as the size, external appear
ance and general arrangement have not been materially changed. A
more careful observation reveals the fact that about one-fourth of
the prescriptions have been replaced by new ones, which is a decided
improvement as many of those discarded involved the same principles
even though they were not exactly duplicates. The text is made to
conform more closely with the present edition of the Pharmacopoeia.
Wherever "Fluid extract'' occurred it has been changed to "Fluid-
extract". Final e has been added to several substances as acetanilide,
antipyrine etc.
The book is divided into two parts. In the first part the sub
stances are arranged alphabetically and the incompatibilities of each
are given. The second part contains 400 prescriptions, some of
which are given in Latin with genative endings while others are ab
breviated or given in English. This gives the student an opportunity
to re-write them in Latin. In the case of phenol it might have
been better had the author used the present official name in some
of his Latin prescriptions instead of the old Latin name. In 24
prescriptions containing phenol the official name appears but three
times, and then only in prescriptions written in English. The pres
criptions are followed by excellent criticisms. The book should be
in every pharmacy and should be studied by every pharmaceutical
student. .4. B. Stevens.
Handbuch deh Pharmakognosie. Von Dr. A. Tschirch, Professor
der Pharmakognosie etc. an der Universitiit in Pern. Liefer-
ungen 2—4. Verlag von Chr. Herm. Tauchnitz in Leipzig.
1908. M. 2.00 h Lieferung.
Fasicles 2, 3, and 4 of this new reference work in pharmacognosy
have appeared in rapid succession and comprise about 110 pages of
text, three original geographical maps, and 230 half-tone illustra

tions of which 20 are full page plates. Again it may be stated that
the illustrations constitute one of the most valuable features though
there is a tendency toward redundancy Occasionally we find a
picture that is much below the general standard, as for example the
one of the harvesting of peppermint, which also is incorrectly labelled
as taking place in Mitcham (U. S. A.).
With characteristic thoroughness a classified list of the most im
portant wild and cultivated medicinal plants collected in a half
hundred provinces, states and countries is presented. Several errors
in spelling and the use of capitals have crept in wherever the author
attempts to use the common names of English and American drugs
in place of the botanical nomenclature, but these are so few in
number that they may be overlooked.
The chapter on collection of drugs presents an interesting
historical survey of the methods in vogue in all parts of the world
from remote antiquity to the present time. Superstitions, myths,
and traditions influencing collections in earlier times are compared
with the generally scientific principles governing collection in our
time, though it must, be said that even in earlier periods drugs
were collected to a large extent under intelligent direction.
The treatment of drugs after harvesting is given thorough con
sideration. In detail the degree of heat used in drying, the rate of
drying, the physical and chemical changes induced by drying, action
of sunlight, enzyme action, sweating, fermenting, curing, liming,
bleaching, steeping, garbling, packing, etc., receive attention. Especi
ally interesting is the treatment of Cinchona, Cinnamon, Cacao,
Coffee, Tea, Tobacco, Opium, Sago, Tapioca, Turpentine, Citrus Oils,
Aloes and others.
The chapter on trade routes and methods of transportation
employed in distributing crude drugs throughout the world is very
complete and illustrates the tremendous strides taken in the develop
ment of transportation from the crude and primitive methods of
earliest times to the present. This portion of the work is accompanied
by three maps two of which are entirely original and were prepared
jointly by the author and the well known pharmaceutical writer and
historian Fr. Hoffmann. It is safe to say that this work, when
finished will present the most complete treatise on pharmacognostical
geography extant.
A perusal of the four fasicles of this encyclopedia of pharma

cognosy must emphasize the fact that there is much more to the
study of pharmacognosy than mere ability to identify a couple of
hundred of crude drugs. If pharmacists would but know it, there is
presented in this contribution a wealth of material which could be
employed in instructive advertising that would bring greater profes
sional and financial success. 0. Schlotterbeck.
Kei'ort of Progress by the National Syllabus Committee re

presenting the boards and schools of pharmacy in the United
States and outlining a minimum course and syllabus. Pam
phlet, pp. 30. Published by The New York State Board of
Pharmacy. Sept 15, 190H.
Let us hope that good may come from the efforts of the Con
ference Committee even though their report of progress may give
rise to more criticism than praise. It is certainly a thankless job
which they have undertaken. Indeed it is a question whether satis
faction can ever be arrived at in this manner. However, if good be
done by such a procedure, we possibly ought not be too critical.
Yet one is forcibly reminded of one of Mephistos' remarks to the
student in Faust, viz., that about crystallized people which the sa
vant from the inferno had met in his wanderings. However, the
attribute should not for a moment be thought applicable to the
writer's friends on the committee, for there are some wideawake
teachers among them. Possibly the "graphics'' have conjured up
the vision. Later we may take up the principles involved in the
attempt to bring about greater unity in instruction and examina
tions. E. K.
A laboratory outline of quantitative analysis including re

cognition and estimation of organic compounds. Arranged for
the use of students at the University of Illinois School of
Pharmacy by William A. Puckner. Brochure, pp. 32.
Chicago. 1908.
This pamphlet is carefully compiled and reveals clearly that
Professor Puckner takes his duties as a teacher quite seriously. The
text is reduced to a minftnum and is so written that it not only
imparts specific information, but compels the student to think for
himself and to look up other references if his information on a given
subject has become rusty. Both qualities are admirable in a guide

for students.
Whether anything is gained by introducing ionic dissociation
into some of the problems will, unquestionably, appear doubtful.
The typogniphical error accidentally discovered on p. 12, viz.
(S08)" + H20 + 2l° = (S04)" + 2H.l' no doubt, will cause some
students to scratch their heads, as may the substitution of "and"
for "to" in the line above. Rather more serious is the statement
(p. 23) that the U. S. P. aBsay processes for aldehydes in oil of
cinnamon and oil of lemon are "based on condensation with sul
phite" without modifying this statement.
The pamphlet certainly must prove a great aid to Professor
Puckner's students as well or to himself and his assistant. E. K.
Schimmel & Co.'s works. Miltitz near Leipzig.

This neatly gotten up volume will be greatly appreciated as a
souvenir by those who have enjoyed the opportunity and privilege
of seeing the estate with its fine office building, its factory buildings,
club houses, villas for officers and dwellings for laborers each with
garden, laboratories, rose and peppermint fields, even its own post
office and railway station. As a whole, the estate is a model factory
site in the midst of grain fields and flowers, where many of the
workmen can enjoy even their midday meal ih the family home,
where early hours of the morning can be spent in the garden and
the evening in the club house or in the not far distant city of
Leipzig.
The small volume is richly illustrated and the colored reproduc
tions of the dwellings as well as the chapter on "Wages" will prove
exceedingly interesting to modern students of sociology. That the
labor leaders of Leipzig should be "mad" at the firm because the
employees do not attend socialistic meetings, one who has seen for
himself, can readily understand. If the labor and factory problems
can be solved, here is an object lesson as to how the solution may
be wrought out. The book is dedicated to the "friends" of the firm.
Well, may they take pride in such friendship. E. K.
Volume 26. DECEMBER, 1908. Number 12.
Precipitated Sulphur. *
By S. M. Sorley.
The older histories of chemistry1 informed us that the prepara

tion of "milk" of sulphur was first taught by Geber and even more
recent historical writers2 stated that while many of the numerous
writings attributed to Geber were spurious, the one in which the
above mentioned process is described, viz: The "de inventione veri-
tatis" was unquestionably genuine. These statements placed the
oldest records on precipitated sulphur as far back as the eighth
century.
However, according to the more recent investigations of Berthe-
lot and also those of the orientalist Steinschneider, 3 the book
"de inventione veritatis" is now, like all of the Latin works o*
the middle ages formerly attributed to Geber, regarded as apo
cryphal, and placed later than the middle of the fourteenth century.
The Latin text of the preparation of precipitated sulphur is of
special interest, inasmuch as it reveals the fact that the term "milk"
of sulphur was originally applied to pure precipitated sulphur and
not, as has been claimed by English writers,* to the mixture of
precipitated sulphur and calcium sulphate, the prosecution for the
sale of which caused such a flutter among English chemists and
druggists during the past century. Herewith it is quoted : 5
"Sulphur vivum clarum et gummosum tere subtilissime, et coque
in lixivio facto de cineribus clavellatis et calce viva, quousque clarum
videtur; quo facto extrahe at move cum baculo, et caute extrahe
illud, quod cum lixivio egressum babuerit, partes grossiores inferius
reliquendo. Illud autem extravtum infrigida parum, et impone ei
* From the laboratory of Edward Kremers.
1 Kopp, Gescblchte der Chemio (1845), Bd. 3, p. 301.
2 E. v. Meyer, Geschichte der Chemle (1889), p. 24.
» See E. t. Meyer. A Ht»tory ol ChemlBtry (1906), p. 312, for reference.
* Among them Redwood.
* Kopp, L c. from Geber, De inventione veritatis.
(353)
quartnm ejus de aceto bono, et ecce totum congelubitur ut Inc.

Lixivium extrahe clamm, quoad poteris, residuum ad lentum desicca
igiwm at serva."
From the above quotation it will be seen that the solution of
sulphur is effected with milk of lime and its reprecipitation with
acetic acid. Acording to Jose de Chesne,0 (1613) lac, cremor or
butirum sulfuris is prepared by precipitating it from its solution in
oleum tartari (solution of potassium carbonate) with vinegar (acetic
acid). 7
According to Glauber (1689) lac sulphuris was precipitated from
its solution in aqueous sodium carbonate with wood vinegar.0
According to Lemery (1756) the magistere de sufrei0 can be pre
pared by "dissolving the sulphur in an 'alkaline salt' and precipi
tating it with an acid."11 Here we possibly have the first general
statement which may have led to the use of sulphuric acid as pre
cipitant. In the specific directions, however, Lemery mentions
"distilled vinegar" as precipitant. In his commentary on these di
rections i2 he points out the fact that a mineral acid precipitates
more sulphur than does the acetic acid directed to be used and at
tempts to explain the causes of this difference. 1a
If these data found in a late edition of Lemery's Cours de chymie
are also found in the earlier editions which are translated into Eng
lish, one can comprehend why an imperfect understanding of the
chemistry of this subject should have caused the editors of the Lon
don Pharmacopoeia of 1721 —, the first edition in which a formula
for the preparation of this article is given — to direct "spirit of
vitriol"14 to be used, also why they allowed both quicklime and
• Schelenz, Geschichte der lMuinnacie, p. 418.

T Josephu* Quercetanus, "Pharmacopoea dogmnticorum restituta," Lips, 1613.
9 "Take sulphur reduced into powder, one part, of fixt niter two parts, put
them in a cucurbit, pour thereon twice an much water as they both of them weigh,
viz: Hix parts. Boil tliem about one hour in sand, in which boiling the liquor of
the fixt niter, will dissolve the sulphur into a red solution. Strain It through cap
paper, and precipitate it by the acid spirit, then weigh It, and you shall nave a
white and subtile powder, profitable in the diseases of the lungs."
The books of the highiy experienced and famous chemist, John Rudolph Glau
ber, London 168'J, Part 11, p. 102.
to For the purpose of greater exactness, Lemery states that It has been sug
gested to make a distinction between "milk of sulphur" and "magisterium of
sulphur;" the former being the precipitated sulphur suspended in water, the latter
the iidryCours
precipitate. Cours de chymie,
de chvmle (1756), p. 561.p. 562.
" Ibidem, p. 562.
is Ibidem, p. 562c.
t* In this connection It should also be remembered that nccordlng to Stahi's
theory, all acids were regarded as mere modifications of sulphuric acid.
salts of tartar to be used indiscriminately as solvent. 15 The use of

the former naturally resulted in a preparation consisting largely of
calcium Hulphate, the use of the latter in a relatively pure precipi
tated sulphur.
In "An essay for the reformation of the London Pharmacopoeia"
(p. 74) the author points out that quick-lime is the cheaper and
therefore usually employed. While he recognizes that with the pre
cipitated sulphur there is "exquisitely mingled"' some "neutralized
salt" formed by the quick-lime and the vitriolic acid as he supposes,
he claims that the amount is but "very small." The method with
quick-lime is also regarded as more ''eligible" because it "makes the
Lac somewhat whiter."
This sort of reasoning evidently prevailed and the "reformation"
of the London Pharmacopoeia resulted in the exclusion in the 5th
edition (1840) of the salt of tartar as solvent.
On the emission of salt of tartar, as the equivalent of quick-lime,
for the purpose of dissolving the sulphur (Comp. 4th and 5th re
visions, viz. 1721 and 1746), Pemberton makes the following re
marks :
"There is a similar preparation directed in the books of chem
istry, with sulphur and alkaline salt; both that and this being
described under the same name of lac Bulphuris, or milk of sulphur.
But with the salt the precipitated powder will not look as white as
this; therefore the precipitation is not in practice ever made after
that manner, though in our former pharmacopoeia either way of
operation is directed promiscuously. But it was chosen to prescribe
here only the method in use.
The change of official title from Lac Sulphuris to Sulphur Prae-
cipitatum'l0 was made because the preparation in question is a
is Lac sulphurla:
R. Sulphuris partem unam
Calcls vivae, rel Sails Tartari partes tres
Coque in Aquae Fontanae q. a. ad solutionem Sulphuris.
Filtra callde; praeciplta cum Splritu Vitrioll; edulcora, & sicca.
(Pharmacopoeia Collegtl Kegalis Meillcorum Loudiuensls
1721 C. M. P.)
Splrltns vitrioll is here evidently used synouymously with oleum rltrloll. Al
though the term splrltus vitrioll Is not given aB a synonym under oleum vltrloll,
nor given in the index, the Spiritus Sails Is prepared in an analogous manner.
i« Sulphur Praeclpltatum.
Kali sulphuratl p. unclam sex.
Aquae distillatae p. Ilberamus unam cum semlsse.
Acidl vitriolic! dilute quantum satis sit.
Coque Kali sulpburatum In aqua dlstlllata donee soleatur.
Ltquorem per chartam cola, cul adde acldum vltriolicum. Pul-
verem praeclpltatum lava affusa saepius aqua donee insupidus
Sat.
powder and not a milky mixture as the older name would indi
cate. 17
Nevertheless in the 6th edition (1788) the quick-lime was dropped
and precipitated sulphur directed to be prepared from Kali Sulphur-
atum,18 vulgo Hepar Sulphuris by precipitation with sulphuric acid.
Commenting on the different appearance of the new preparation,
Healde remarks: "This (The new Pharmacopoeia, 3rd ed., p. 144)
preparation is not so white as that of the last Dispensatory, which
was made with quick-lime, but it is more purgative."
t7 Sulphur Praecipltatum :
Flores sulphuris cum trlplo calcis vlrae pondere coqnantur in
aqua ad solutlonem sulphuris, et liquor per chartam coletur;
deinde, spiritu vltriolt terrul addito, praeeipitibatur pulvis, qui
aaeplus affusa aqua lavandus est, donee omnius insipidus fiat.
Pbarm. Coll. Ked. Meil. Lond. 1757, p. 55 (C. M. P.). Pemberton (Dispensatory
4th p. 209) gives the following translation: "Boll flowers of sulphur with thrice
their weight of quicklime, till the sulphur Is dissolved, and Alter the solution
through paper; then with weak spirit of vitriol make a precipitation, which is to
be often washed, till it has become quite inclpid.
In the "Index Nomlnum mutatorlum" attention is called to the fact that
"Lac Sulphuris," the name formerly used, Is to be replaced by the new name
Sulphur praecipltatum.
The Committee of Revision in its Narrative states that "Here lac sulphuris.
which is a powder, is now more properly called sulphur praeclpitatum."
(Pemberton : Dispensatory 4th Ed., p. 58.)
is Kali sulphuratum.
Florum sulphuris p. unclam unam. Kali p. unctas qnlnque.
Salem sulphuri, lento Ique coque facto, assldua agl tatrooe
tmmlsce, donee In unum cbeant.
Ibidem p. 1 74.
The Apothecary, A Literary Study.*
By Edward Kremers,
The third cut, fig. 51 of the original treatise, represents the

barber. His quarters appear more commodious than those of the
apothecary and his habit reveals the man with an appreciation of
what is fashionable. His shop is provided with a large window and
the aesthetic sense of proprietor and customers is satisfied by a vase
of cut flowers on the window sill. The barber is not merely a
man of skill in the trimming of the hair or the shaving of the
beard, he is skilled likewise in the preparation of healing ointments,
in the dressing of wounds, the setting of broken bones, the curing
of syphilis, the extraction of teeth and surgery of the eye. As sym
bols of his minor surgery, bandages are suspended from the ceiling
and labled containers are mounted on a shelf.
The functions in which the barber of the cut is engaged are,
however, strictly those of the barber proper, viz. hair cutting and
shampooing. In this connection it is of interest to note the disposi
tion which the barber makes of the comb while using the shears,
also to note the arrangement of the water reservoir used as douche
by the assistant. This convenient disposal of the comb is one which
the writer observed even as late as twenty years ago in Bonn in a
barber shop frequented not only by students but also by the officers
of the hussars whose barracks were in the neighborhood. The globe
like arrangement over which the towel is hanging is evidently a
hollow metal sphere that serves as a receptacle for untidy towels,
such as one can see at the present time in front of the restaurant
near the entrance to the Sorbonne at Paris.
The dentist, as becomes apparent from a first glance at the
cut, is an itinerant quack. His general appearance is characteristic
of the type. His diploma with the great seal is "conspicuously dis
played" as must be the registration certificates in accordance with
our modern pharmacy laws. He openly invites all who have tooth
ache. His modus operandi is characteristically expressed by the
* Continued from page H48.
word "ausbrechen," to break out, rather than to pull out or extract.

Yet he advertises his ability to remove teeth without pain "as
children are born," i. e. without pain to himself. However, the term
"ausbrechen" and the expression on the face of patient causes the
reader to be thankful that he does not live in the age of the six
teenth century dentist.
The "tooth breaker's" activities, however, are not restricted to
the removal of teeth which he ties to strings and exhibits to the
curious passer by. He also sells "Petrolium," note the spelling, and
wormseed. Whether the contorted tape-like affair on the table is
an unwelcome host removed from a patient, can not be stated
positively, but may be surmised. He also offers for sale theriac —
note the large container — likewise a fungus that will cause the death
of mosquitos. Furthermore, he offere for sale ointments for fleas
and lice, also powders for rats and mice. This last sentence happens
to reproduce in a fair way the rhyme of Hans Sachs.
Although the barber advertises that he takes pleasure in drawing
superfluous blood, this seems to be also an occupation of the
cupper. His German name, however, as well as the cut representing
this important member of human society, would seem to indicate
that bathing was his main occupation and that cupping appears but
as an incident to the bnth. Like cupping, bathing in the sixteenth
century was evidently not a thing to be indulged in too frequently.
According to the cut of .lost Ammann it would, appear to have been
something of a family affair. The cupper is also a masseur and hair
dresser.
A sixteenth century balance maker is naturally of some in
terest to the pharmacist, for he not only made the scales for weigh
ing gold coins, but also for weighing spices and, no doubt, drugs.
The oil maker manufacture oils, not only for table purposes
but also for medicaments. The burr stone is drawn by a horse and
in the rear an oil press is visible. Among the oils which he produces
are olive oil, walnut oil, oil of pine, oleum lanri, hempseed oil and
linseed oil. The invention of the process for making these good
things is attributed to the goddess Minerva.
The book closes with an admonition, by Hans Sachs, to every
one to do his duty to God and man, to avoid all that is evil or of
ill repute, and to live in the "fear of the Lord, the beginning of all
wisdom.
PllA KIIA CFA TICA I. RKVl FAV. 359
28o(fjct7l>fr §af tin Wfcn gati/

g)«nfcftcn tdj aufftrcdgw fan/
^)a6 aucfe girt <Saf6n/fdr »nt> icuj?/

3ucfe p«(M<r filr Qia^n vno
Fig. 52. The Dentist.

3Bof|w ins <2>a& CRci'clj vnte 2(rm/

&a&iftiwinbci(Uit}ctwarml
$?it njolfcrjmacfccr Xau$ ma"cuclj tt>cfd)W
&cmt auffDic "Oki.baiict' cucl? fcgt/
SOfat iaffti Dad t>brta, SSluf au f;ttifbti/

2D<tm mrtbmi c3anncnfabrtfraui>f/
Fig. 53. The Cupper.

3fcfc ma$ to* SBaa/gtofj wtoc tUial

fOttraOarfcp ©mtc^f in gcmcin/
JDk fafcncf tdj mtt SDlcfltogfd&afa/
523o man mm antojjtfcut bcjaln/
C9?ac^ aucfc m to Xaitfct n ®oltn>ag/
tftacfc ten fw&cn t>t'c $a uffTc ut frag/
*Dar$tt anbtt TOrf?tt>dg (cm gut/
<Df< man iti£r4m<n&raijcfccn thue*
Fig. 79. The Balance maker.

©fanestfrp <tf fcfc $uUttitl

Su <f|ot tmt> Zttttity attjctt/
Xori5f/ât#5(/ândl/Daro(
3$ Dfc <35cifr famUn MtKrgcffbi/
Scrmatmcnlwt> tarnacfe aM^ptrflfcn/
ADarmu Dae dl trfj tarauf? bring/
SSftiwrua crfu n t> t>tcfc d»i <j.
c «
Fig. 98. The OU maker.
PHARMACE UTWA L REVIEW. 303
Also Bi ii (1 hie geztiget an

Yierstehen vnd hundert Peron,
In t'juipteru, Kiiustn vnd Handarbeit,
Doch vndersehieilen ferr vnd weit,
Vj\\ eim Fiirbild, dnss jederman
Auff sich selb sol nut achtung hnn,
Dn*s in seinem Befeleh vnd A mpt,
Auss vntleisx gar nirhts werd versaumpi :
Dergleich Kiinstner vnd llandwereksleut,
Sollen aui'h htindlcn gar vertreuwt,
Einer deiti andren dienpu sol.
Mit seiner arbeit reoht vnd wol,
Wiu er begort in reenter treuw,
Vnd hab vor alien Lnstern scheuw,
Als eigen uutz, vnd mtissig gan,
Weil Gott ein wiheu wen hat daran,
Der vns herre'cht in dieser zeit
Sein Brot durch viel miih vnd arbeit,
Es sell so ring es jmmer woll,
Vns doch daran begniigen sol,
Gott darumb sngen Lob vnd Ehrl
Weil vns seiu Hand nlle prnehr:
Wer abi'i. fuhrt ein blosen Handel
Vunutz Gottloss diesen Wandel,
Auff dnss er nur gross Reich hnb.
Der kehr vmb, vnd lass darvon ab,
So entgeht er viel vngemactis
Nie vnd aucli dort, spricht Hans Sachss.
Thymoquinone and Hydrothymopinone.*
By Nellie Wakeman.
Revision of Ji.s-5 Terpatriene — Diol — 2.5.

Synonyms. Hydrothymoquinone.1 Oxythymol.8
Thymohydroquinone.2 Dihydroxycymene.8
Thymoquinol.8 Hydroxycarvacrol.
Thymoilol.4 ji-8-b Menthatriene—diol-2.5.8
History. Hydrothymoquinone was first prepared in 1853, by
Lallemand,7 who called it thymoilol, because it resulted from the
reduction of thymoil (thymoquinone) with sulphurous acid. This
in turn received its name from thymol the so-called stearoptene from
oil of thyme, obtained from Thymus vulgaris. To the hydrothymoqui
none Lallemand assigned the formula C24H18O4, although he had
previously given to thymol the formula C20H14O2 (= C10H14O).
This discrepancy was noted by Kekulti, who (1867) in his Lehr-
buch,J pointed out that it did not become apparent why thymol
with 20 carbon atoms should yield upon oxidation the thymoilol
with 24 carbon atoms.

I J. pr. chem , 111. p. 54 ; Annalen, 170, p. 302.
a Meyer and Jacobseu, Bd. II, p. 447; Beilsteln, Suppl. Bd. II, p. 568.
» J. C. 8., 80 I, p. a29.
* C. r., 38, p. 1022; Annalen, 101, p. 120.
» Bellsteln, Bd. II, p. 970.
« Beilsteln, Bd. II, p. 970.
1 C. r., 38, p. 1022; Annalen, 101, p. 120.
s For purposes of nomenclature, methyl p-isopropyl hexamethylene has been
. designated terpane (v. Baeger, Ber. 27. Bd. I, p. 436), also menthane
(Wagner, Ber. 27, Bd. II, p. 16a8). The corresponding hydrocarbons of
/\ the next lower degree of saturation, vll. CioHm, terpenes (not the terpene
[a'al CioHia of Kekultf) and menthene; those of the formula of saturation
|b4 s| Cnllan—4 follow as terpadlenes und menthadlenes ; those of the formula
\ / of saturation CnH2n—6 as terpatrlenes and mcnthatrienes. For the use
I of the numbers, those with reference to the carbon atoms as well as
X. those indicating the position of the double linkage, the "J", see v. Baeyer,
10/ \9 Ber 27, Bd. I, p. 436.
» Lehrbuch, Bd. 8, p. 148.
Car s tan j en 10 in 1871 revised these formulas and ascertained

that hydrothymoquinone has the formula C10H14O2. While Carstan-
jen set right the empirical formula of this compound,
CHs h>8 >dea of the position of the hydroxy11 groups
^ (2 and 3, with methyl and propyl 1 and 4) were
wrong. The positions of the two hydroxy groups
HC/ %COH assumed at present appear to have first been
assigned, as one of two possibilities, by Carstanjen
HOC\^^/'CH jn hi8 formula for oxythymoquinone.*
U The natural occurence of a derivative of hydro.
CH thymoquinone in the vegetable kingdom was first
/\ pointed out in 1873, by Sigel12 who found the
(<h3 ^CHs dimethyl ether in the oil of arnica flowers. (See
Occurrence.) The diatomic phenol, as such, was
first isolated from a monarda oil in 1901 by Brandel,1a who had
previously isolated thymoquinone from the same source. The pre
sence of the two in the same plant gave rise to the thymoquin-
hydrone hypothesis of plant pigmentation. From data since col
lected it would seem probable that hydrothymoquinone, as well as
other diatomic phenols may be widely distributed in the vegetable
kingdom. The presence of these (either as such, or in the form of
glucosides) together with that of their corresponding quinones,
enables us to understand much that has been hitherto incompre
hensible in the interpretation of the color phenomena of plants.
Occurrence. As the diatomic phenol.
Hydrothymoquinone occurs, as such, in several species of Monarda,
having been isolated and identified (melting point and Liebermaim'st*
quinhydroue reaction) by Brandel in the volatile oils, not only of Monarda
fistulosa,15 but also of Monarda citriodora.™
As dimethyl ether.
Hydrothymoquinone occurs as the dimethyl ether in the volatile oil
distilled from the flowers of Arnica montanai' where it was first found by
Sigel in 1873. The presence of the hydrothymoquinone was here proved
by heating the dimethyl ether in sealed tubes with hydriodic acid when
• Journ. pr. Ch., 128, p. 417.
t0 J. pr. Chem., Ill, p. 54.
it J. pr. Chem., Ill, p. 67.
u Annalen, 170. p. 345.
t3 Ph. Rev., p. 244; Chem Centralbl., 72, II, p. 1007.
t* Ber. d. D. Chem. Ges., 18, p. 3194.
is Ph. Rev., lit, p. 214.
l» G.-H.-K., The vol. oils, p. 153. (Ph. Rev., 24, p. 117.) Ph. Rev., 22, p. 153.
1' Annnlen, 176, p. 345.
hydrothymoquinone and methyl iodide were obtaiued, the hydrothymo

quinone identified by both its melting point and by elementary analysis.
Methods of formation and preparation. I. By the re
duction of thymoquinone with sulphurous acid.
(a) . In 1833 Lai lem and18 prepared hydrothymoquinone (which he
called Thymoilol) by reducing thymoquinone with sulphurous acid.
Thymoquinone was placed in an aqueous solution of SO2 and allowed
to stand when it soon took on a dark violet color and was changed in a
few days to a white crystalline substance, slightly soluble in warm water
and very soluble in alcohol and ether. This white substance Lallemand
called thymoilol, while to the violet colored intermediate product he gave
the name thymeid.
(b) . Cars tan j en , 10 in 1871. used the method of preparation employed
by Lallemand, modifying it only by passing a current of SO2 gas into
thymoquinone suspended in water. He, however, purified the product by
recrystallizing from hot water containing u little sulphurous acid.
When this method of preparation and purification was employed by the
writer,20 glistening white crystals, exactly as described by Carstanjen were
obtained.
II. By the reduction of thymoquinone with light in the presence
of alcohol.
By exposing an alcoholic solution of thymoquinone to the light Ci a -
mician21 and Silber, in 1901, obtained hydrothymoquinone, the car-
bonyl group of the ketone being reduced to a hydroxy group, while the
alcohol was at the same time oxidized to acetaldehyde. This method of
preparation was tried with small quantities of material in the laboratory22
and in a few days a white precipitate of hydrothymoquinone was obtained.
III. By the reduction by light of thymoquinone in a limonene
solution.
Solutions23 of thymoquinone in limonene when exposed to light first
turn dark, then in time become completely decolorized, the thymoquinone
being reduced and hydrothymoquinone, sparingly soluble iu limonene, pre
cipitated. The exact nature ol this reaction is not. understood. That it is
dependent upon the action of light is proved by keeping a duplicate solu
tion away irom the light when no such reaction takes place.
Purification. Lallemand24 recrystallized hydrothymoqui
none from hot water; Carstanjen25 from hot water containing a
little sulphurous acid.
When recrystallized from hot. water alone a dirty white product results,
ts C. r., 88, p. 1022; also, Annalen, 101, p. 120.
is J. pr. Cham., 111. p. 54.
2" Ph. Rev., 26, p. 331.
»i K. A. L., (5), 10 I, p. <J6, also Chem. Centralbl., 72 I, p. 77.
« Ph. Rev., 20, p. 331.
" Ibid., p. sai.
»* 0. r., 38, p. 1022.
35 J. pr. Chem., Ill, p. 54.
when from hot water containing sulphurous acid beautiful white heavy
crystals are formed.-"
Physical properties. Melting point. Lai 1 em and 87 found
the melting point of hydrothymoquinone to be 14.")°, Carsta njen28
observed that it melts at 139.5° and sublimes unchanged at higher
temperature, Sigel20 gave 139°—140° as the melting point; and
Brandel30 140°.
After recrystallizing first from hot water, then from hot water
containing SO2, 140° was observed as the melting point.31
Solubility. Lallemand32 and Carstanjen8a found hydrothy
moquinone difficultly soluble in cold water, quite readily soluble in
hot water, and very soluble in alcohol and ether.
It was observed34 to be almost insoluble in limonene, hexaue,
and benzene but soluble in glacial acetic acid. In ammonia it dis.
solves producing a red liquid.
Form and color. Lallemand35 describe..* hydrothymoquinone
as existing in white crystals; Carstanjen38 as glistening white
heavy crystals, "combinations of four sided prisms with two pyr
amids." Crystals obtained37 by recrystallizing from hot water con
taining SO2, were of a brilliant whiteness, and when observed under
the compound microscope were found to be made up of short prisms,
resembling cubes, and flat four sided plates.
Chemical properties. Oxidation to thymoquinone.
While, when perfectly pure, hydrothymoquinone does not readily
change, under certain conditions not always understood, it is oxyd-
ized by the oxygen of the air to thymoquinone, forming thmoquin-
hydrone as an intermediate product. This oxidation is greats-
facilitated by such oxidizing agents as nitrous acid, ferric chloride,
chromic acid, manganese dioxide, oxidase, 38 and even quinone.39
Additive properties. When an alcoholic or ethereal solution of
hydrothymoquinone is mixed with a similar solution of thymoqui-
3« Ph. Rev., 26, p. 331.
" J. pr. Chem., Ill, p. 54.
»s J. pr. Chem., Ill, p. 54. '
2» Aunalen, 170, p. 845.
30 Ph.
Ibid.,Rev.,
26, p.19,331.
p. 244.
si
3' C. r., 38, p. 1022.
33 J. pr Chem., 111. p. 54.
3* Ph.r.,Rev.,
38, p.26,1022.
p. 381.
s« C.
3« J. pr. Chem., Ill, p. 54.
3» Ph. Rev., 26, p. 831.
3s ph. Rev., 22, p. 190.
s» Chem. Centralbl., 69 I, p. 887.
none,40 or of ordinary quinone, 41 it is apparently added to these

ketones upon the evaporation of the solvents. Its capacity to add
on is best explained by the analogy of monatomic alcohols form
ing alcoholates with aldehydes, e. g. ethyl alcohol to trichloraldehyde.
Hydrothymoquinone will add thus
i1 -o/R
-°\r"
{ —H
Revision of Ja-6 Terpadiene—dione—2.5.
Synonyms. J3'6 Menthadiene-dione-2,o. l-Methyl-4-methoaethyl-
quinone.1 Thymoquinone.2 Thymoil.a
History. The history of thymoquinone is almost identical with
that of hydrothymoquinone, the two substances in almost every
instance, having been prepared and studied together. It was first
prepared by Lallemand4 by the oxidation of thymol. From its
source Lallemand called the new product thymoil and its reduction
product thymoilol. To thymoquinone Lallemand gave the formula
C12H18O2. In 1875 Carstanjen5 revised this formula, together
with that of hydrothymoquinone, assigning tlnrmoquinone the
formula C10II12O2. In the location of the ketone groups, however,
he made the same error that he had made in locating the hydroxy
groups of hydrothymoquinone. The formula, adopted at present, is
based on that of hydrothymoquinone, viz. :
0Hs
I
C
HC/ \C=0
o=c\ yen
('II
CHa CHs
*o Ber. d. D. Chem. Gesell., 18. p. 8196.
*i Ph. Rev., 26, p. 882.
t Bellstein, lid. 3, p. 864,
» J. pr. Chem., Ill, p. 54.
» C. r., a8, p. 1022.
»s C.
J. r., 88, p. 1022.
p. Chem., Ill, p. 54.
In 188o Liebermnnn8 prepared thymoquinone from thymol,

through nitrosothymol and amido thymol, and studied its properties
together with those of its polymer, polythymoquinone. Since that
time it has been repeatedly prepared from both thymol and car-
vacrol.
Thymoquinone was first found as a natural product in 1891, by
Brandel7 and Kremers who isolated it from the volatile oq
distilled from Monarda fistulosa.
Occurrence. Thymoquinone occurs in the volatile oil of wild
bergamot (Monarda fistulosa) in the nonphenol portion of the oil
where it was found and identified (melting point 45°, elementary
analysis and quinhydrone reaction) by Brandels and Kremers
in 1901. Its presence in Monarda citriodora0 where hydrotbymo-
quinone has actually been found is indicated by the red color of the
oil, due, in all probability, to thymoquinhydrone formed by the
union of thymoquinone with hydrothymoquinone.
Methods of formation and preparation. The several
methods of preparing thymoquinone all resolve themselves ultimately
to the oxidation of hydrothymoquinone to thymoquinone. The
minor differences group themselves into three classes. First, as to
the material used as starting point, viz. thymol or carvacrol;
secondly, as to the method of preparing the hydrothymoquinone;
and lastly, with reference to the oxidizing agent.
I. By oxidizing hydrothymoquinone with MnO2 and H2SO4.
(a) Starting with thymol, through thymol sulphonic acid.
Lallemand10 in 1853 first prepared thymoquinone by dissolving thymol
in an excess of H2SO4, thus forming the thymolsulphonie acid. The ortho
acid is first formed und this by standing or by heating is changed to the
para acid. Five or six times its volume of water is next added. This
hydrolises the thymol-sulphouic acid, forming hydrothymoquinone and sul
phurous acid. An excess of Mn0» is then added oxidizing the hydrothymo
quinone. The product is distilled and recrystallized from hot alcohol, or
from alcohol and ether.
(b) Starting with carvacrol through carvacrol sulphonic acid.
In 1877 Carstanjen11 applied the method of Lallemand for preparing
thymoquinone to carvacrol, obtaining "cymophenolchinon", which he identi
fied with thymolquiuone.
e B. d. D. Chem. Gesell., 18, p. 319-t.
7b Ph. Rev.,11),19,p. p.200.
200.
Ibidem,
9t0 Ibidem, 22, p. IsS.
C. r., 38, p. 1022.
" J. pr. Chem., Ill, p. 54. «
II. By oxidizing hydrothymoquinone With KaCraCH and H2SO4.

(a) Starting with carvacrol through carvacrol sulphouic acid.
Rychler,12 in 1892, prepared thymoquinone by dissolving carvacrol
in an excess of H2SO4, then diluting with several volumes of water, adding
an excess of KUO2O7 and distilling with steam. Rychler reports from this
method a yield of from 68—70%. He also claims that a larger yield of
thymoquinone may be obtained by using carvacrol as a starting point,
than by startiug from thymol, and says that K2O2O7 is superior to MnOa
as anjoxidizing agent.
(b) Starting from thymol through thymol sulphonic acid.13
Rychler's method was employed by the writer, using thymol as a start
ing point, with no very satisfactory results. The yield being never more
than 20—25%.
(c) Through nitroso thymol and amido thymol.
Liebermann14 and Ilinski, in 1895, employed the method of Shiff15
for preparing nitroso thymol. From this the amido thymol was prepared
by dissolving in ammonia and precipitating with H2S. This precipitate
was dissolved in an excess of H2SO4, and K2O2O7 was added to oxidize
the amido thymol, first to hydrothymoquinone then to thymoquinone.
The product was distilled with steam and recrystallized from hot alcohol.
Yield 60%.
III. With nitrous acid, through the nitroso and amido com
pounds. 10
A modification of Liebermann's method was employed by the writer
using the method of Bran del17 and Kremers for preparing nitroso thy.
mol. Sodium nitrite and H2SO« were used to oxidize the amido thymol
first prepared to thymoquinone. By this process a superior product and
an excellent yield were obtained.
IV. By oxidizing hydrothymoquinone with quinone.
In 1889 Biltris18 found that when lukewarm aqueous solutions of
hydrothymoquinone and ordinary quinone are mixed, thymoquinone in
stantly separates while hydroquinone and small quantities of the mixed
quinhydrones remain in the mother liquor.
This method of formation was tested in the laboratory and it was
found that hydrothymoquinone could actually by oxidized to thymoquinone
by quinone in aqueous solution. In alcoholic or ethereal solution, however,
a quinhydrone is precipitated.
« Bull. 8oe. Ch<?m.. 18], 7, p. 24.
is Ph. Rev., 26, p. 332.
t* Ber. d. D. Chem. Gesell., 18, p. 3194.
is Ibidem, 8, p. 150.
i« Ph. Kev., 26, p. 333.
t7 Ph. Kev., 22. p. 250.
is Chem. Centrlbl., 69, p. 887: also Jr. Chem. Hoc., 76, p. 199.
(To be continued.)
The Volatile Oils : 1901 to 1903.*
By /. W. Braodel
Transfer 25 c. c. of this solution by means of a pipette to a specially

constructed weighing flask, Fig. 2, which is connected with un apparatus
shown in Fig. 3. The benzin is evaporated by means of a pump. The
apparatus is so arranged that the benzin drawn off may be ignited at

a jet, and thus indicate the complete evaporation of the solvent. 0.0005
gms. of rhigolene can be detected in the weighing bottle in this way.
171. Oil (Otto) of Rose. G.-H.-K., p. 423.
Properties. S. & Co.59 have determined the following con
stants for oil of rose. Nos. 1 and 2 are their own distillates; nos.
3 and 4 Bulgarian commercial oils; nos. 5 and 6 reliable oils from
Philippople.
The citronellol content was determined by heating 10 c. c. of oil
on a water-bath for one hour with double its volume of cone, formic
acid. By this treatment geraniol and linalool are decomposed,
leaving citronellol as formate, which is assayed by saponification.
The results are always a little too high.
«» S. & Co., Kep., April, 1901, p. 48.
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A sample of Russian Otto of Rose produced in the Imperial

Apanages of Knchetie, Caucasus, according to Roure-Bertrand Fils,
had the following properties:
Sp. (jr. at 30° 0.8308
Rot. power at 20° —4° 16'
Solidifying (it 23° 0.
Stearoptene 33.5 p. c.
Acid no 5.7
Saponification no 4.7
Enters, CHsCOOCroHio 1.06 p. c.
Sap. no. alter acetyl 157.2
Total alcohol, C10U200 49.6 p. c.
Sap. no. after Formyl 114.7
Rhodinol 34.0 p. c.
Gerauiol 15.6 p. c.
The rotatory power of the Russian otto is higher than that of
the German and Bulgarian, hut lower than that of the otto of
Grasse. Its solidifying point lies between that of the German and
Bulgarian.
Parry60 claims that all commercial genuine otto of rose is a
blend ami not the produce of any one district. This is due to the
great number of small peasant distilleries which sell to larger distil
leries which then mix the oil from various districts. The oil is not
alvrays from Rosa damnscena as in Grasse, Cannes, Nice and Leip
zig, the rose chiefly used is Rosa ceutifolia and in Bulgaria great
quan(ities of the white rose, Rosa alba, are used mixed with Rosa
daimiscona. In as much as the various villages grow different pro.
portions of these two roses, the product will vary considerable it
different villages.
A pure oil of rose, distilled only from the white roses, had a
very fine odor, but was, however, outside B. P. limits. The constants
of this sample and also 4. others from individual districts where a
larger amount of white roses than usual are distilled and the limits
of the B. P. are given in the following table:
OIl from Congealing point Sp. gr. at 80" notation Saponification
23.5°—24° 0.8482 —2° 21' 0.9 p. c.
2. " " largely.. 22.5° 0.8540 —2°46' 0.81 "
43. II tt 't 22.0°
22°
0.8509
0.8505
—2° 37'
—2° 4 6'
0.76 "
0.78 "
5. 21.5° 0.8518 -3° 10' 0.90 "
B. P. limits 19.4—22.2° 0.856-0.860
»o Ghem. & Drugg., 57, p. 125.
An oil distilled from the petals only of the rose had a most
exquisite odor, sp. gr. at 30°=0.8580. congealing point 18.5°—19°
and a„= —2° 27'.
According to Holmes61 the odor of oil of rose depends upon the
locality of cultivation, conditions under which roses are grown and
to the still us 'd. 2% acres yield 6000 lbs. of roses which yield 2%
lbs. of oil of rose. The gathering is done in the early morning at
which time they contain the most perfume.
Soden and Rojahn62 have determined the comparative yields of
oil from the fresh and dried petals and calyx. The crude oil is in
each case the total oil extracted and separated from the aqueous
distillate. They have also determined the amount of phenyl ethyl
alcohol in the flowers and the proportion of this constituent to the
total volatile oil. The results are given in the following tables:
Exp. 1. Exp. 8.— 50 kilos <>( fresh Exp. 2.— 50 kilos of fresh Exp. 4.—50
flowers gave flowers gave kilos.
50 kilos of a f> « b a
fri'Hh
flowers. 41.5petals.
kilos of 8.5 kilos ol
calyces.
9.5 kilos of 2.5 kilos of 40.5 kilos ol
dry petals dry calyces. petals
Oil 37.50 gms. 28.00 gms. 2.00 guis. 9.50 gms. 2.50 gms. 23.50 gms.
dio° 0.944 0.940 0.897 0.894 0.946
a" at 34°.... —0°17' —0°40' —0°8'
Cong, pt 28° 29° 25°
Acid no 3.4 3.0 5.5
Ester no 19 16 17
Composition of oils from table above:
1 2a 3a 4a
Oil readily vol. with steam. 10 p. c. 10 p. c. 20 p. c. 27 p. c.
Sp. gr. at 30° 0.845 0.828 0.837 0.866
23° 27° 26° 18—19°
0O 57 50 54
Sp. gr. at 15° 1.020 1.019 1.020 1.012
218—19° 218-19° 218—22° 218-20°
7.5 p. c. 8 p. c. 15 p. c. 3 p. c.
Paraffin like residue 17.5 " 15 " 10 " . n *sts
5 10 ' 5 " 18 ''';
To prove that oil of rose is not so commonly adulterated by
Bulgarian manufacturers and that pure oils can be readily obtained
from these manufacturers, Parry03 has examined 20 specimens of
oil of rose and determined the following constants :
oi Pharm. Journ.. 67 p. 664.
•2 Ber. 34. p. 2803.
«s Chem. & Drugg., 60 p. 390.
Sp. gr. at 30° from 0.8490 to 0.8565
aD from —2° 25' to —3° 17/
Cong. 1>t. from 20° to 23°
Sup. val. (|). c. KOH) from 0.74 to 0.90
P. c. of stearoptene from 18 to 22.5
M. P. of stearopt+me from 33° to 34.5°
Adulteration. Inasmuch as the addition of geranium oil
lowers the congealing point of the oil too far, distillers sometimes
add a mixture of salol and antipyrine which raises the congealing
point.8*
According to Parry65 the determination of the refractive index
is especially valuable to detect adulteration of oil of rose. Geraniol
and Turkish geranium oil have a much higher index of refraction,
while eitronellol has a lower index of refraction. Addition of these
substances to oil of rose can be detected by fractionating the sus
pected oil and determining the nD of the various fractions.
Nd of OH of rose, pure Geraniol Geranium oil Cltronellol

1.46190 1.47923 1.47602 1.45718
1.46095 1.47995 1.48055
1.46148 1.47958
1.46145 1.47850 -
1.46208
Oil of palmn rosu or turkish geranium, is according to Garnett 08

the principle adulterant used. The rank odor of the oil, makes
possible the detection of more than 5 p. c. by smelling. The odor
can more rendily be detected by dissolving the suspected otto in a
little alcohol, diffusing the solution in a large quantity of water,
and comparing the odor with that of a similar mixture of genuine
oil of rose. The limits of sp. gr. as ordinarily used are too wide, they
should be within 0.8525—0 8575 at 30°, and even 0.8575 may be
looked upon with suspicion. «„ varies between —2° 15' and —3° 15' at
27°—30°, but is never dextro. The reason that it is impossible to
obtain freezing point figures agreeing with those given by Bulgarian
merchants, is due to their method of taking the "setting point."
A vial (1 —2 oz.) of otto is placed in a bath slightly above its m. p.
A thermometer is placed in the bath, neither bath nor oil are stirred
and the whole is allowed to cool. The point at which crystallization
is seen to commence on the sides and bottom of the vial, is taken
as the freezing temperature. The limits usually given are too wide.
The B. P. range of 19.4°—22.2° is wide enough. In the author's
«* S. & Co.. Ber., Oct.. 1902, p. 78.
«» Chem.
Chem. && Drugg.,
Drugg., 68,
56, p. 24.6.
•« p. 961.
opinion 19.5°—22° would cover all pure ottos. The mere determina
tion of alcohols by acetylation doe.s not afford very useful results,
as palma rosa oil consists largely of the same alcohols. The ester
p. c. is useful, as the amount of esters in pure rose oil is very low,
3 p. c. while palma rosa oil is about 10 p. c.
Oil of rose is official in the Belgian Pharm., 1903, with the fol
lowing constants: Crystalline, light yellow mass; soluble in equal
vol. of chloroform; solidifies at 18°—20°.
Composition. In the distillation of roses at Schladebach, near
Merseburg. the aqueous distillate is redistilled and a further quantity
of oil and a strong rose water obtained. The water in the retort
has a faint rose odor from which by extraction with ether, Soden &
Rojan67 obtained 0.025 p. c. of oil consisting cfrefly of /3-phenyl-
ethyl alcohol. The oil extracted from the stronger rose water con
tained 35 p. c. of this alcohol. The rose oil contained 1 p. c. of
alcohol. Because of the solubility of phenyl ethyl alcohol in water,
oil of rose obtained by enfleurage should contain much larger
quantities of the alcohol. A sample of French r.'se pomade con
tained 45.5 p. c. of phenyl ethyl alcohol, and an oil obtained by
extraction with a volatile solvent contained 25 p. c. 08
The following constituents, besides geraniol, have been identified
by S. & Co 80 (VValbaum and Stephan70). Phenyl ethyl alcohol,
b. p. 221°— 222° C. at 748 m. m., wus isolated from the residue
(benzoic acid, m. p. 122°— 123°).
A fraction of oil boiling from 55°—100° at 13 m. m. contained
normal nonylic aldehyde (pelargonic acid, b. p. 252°—253°). The
pure aldehyde boiled at 80°—82° at 13 m. m.; sp. gr. at 15° =
0.8277; n„ = 1.42452 at 16° ; aB = ±0°. The fraction also contained
linalool, b. p. 197°—200° at 756 m. m.; sp. gr. at 15° = 0.871;
an at 22° = —7° 33' (citryl-^-naphthocinchoninic acid, m. p. 197°
to 199°).
In the portion of oil boiling above 100°, citral was identified and
also 1-citronellol (citronellyl phtalic silver salt, m. p. 120°—122°).
Darzens and Amingeat71 find that the method of determining
the proportion of terpene alcohols and esters in mixtures by means
of the solubility of the first and insolubility of the latter in 50 p. c.
sodium salicylate solution as first suggested by Duyk, is not even
approximately correct. Experiments were tried with mixtures of
known percents of rhodinol and its esters.
«7
•s Ber.,
Ber., 8a,
a3, p. 1720.
p. a068.
" S. & Co., Rep., Oct., 1900, p. 55.
'0 Bull.
'i Ber.. Soc.
38, pp. 1900,25,2299,
Chim., 2802.
p. 1053.
Literary.
A text-book of botany and PHARMACOGNOSY. Intended for the

use of students of pharmacy, as a reference book for the
pharmacist, and as a hand-book for food and drug analysts.
Henry Kraemer, Ph. 15., Ph. D. Professor of Botany and
Pharmacognosy, and Director of the Microscopical Laboratory,
in the Philadelphia College of Pharmacy, etc. Illustrated with
over 3000 plates comprising about 2000 figures. Third re
vised and enlarged edition. Philadelphia and London. J. B.
Lippincott Company.
Tins book opens with a botanical introduction of about four
hundred pages dealing with the main facts of taxonomy, gross
morphology and internal structure. Plants yielding drugs are then
assigned to their proper places in the botanical system and a chapter
dealing with drug plant cultivation closes this part of the book.
Illustrations of good quality, both original and from outside sources,
are introduced. In general the botanical outline of Engler & Prantl
is followed. In the interests of a stable nomenclature, in the case
of plants growing in the United States, the author has deemed him
self conservative in following Britton's Flora. In view of the in
creasing tendency of botanists to adhere to the Vienna agreement
and more and more to eliminate individual standpoints, one is free
to express the doubt whether a conservative nomenclature is to be
sought at this source. Since the book in hand appeared, the seventh
edition of Gray's .Manual has been issued. This work covers the
northeastern part of the United States and brings the botany of
that region into accord with the Vienna code and may now be
followed as an authority likely to furnish a more nearly stable
nomenclature than we have yet known. The individual chapters
offer a good elementary outline of morphology and histology with
a wealth of illustrative material drawn from medicinal plants. Ob
jections may or may not be made to the contrasted terms of "outer"
and "inner" morphology. One interested in the recent advances in
our knowledge of internal structure may complain because the "stele"
and all developments coming from the stelar point of view are not
referred to. Since, however, the students for whom the book is
written are not likely to become botanists, it may be contended
that through the medium here used, the essentials of plant structure
are as clearly presented as through the more modern one. Although
the chapter on classification of angiosperms does not include distinct
characterizations of the groups discussed, an unusual interest is
injected into the subject by the mention of numerous facts of general
information not related to taxonomy. Indeed, the book as a whole
is extraordinarily full of these running observations on points of
general interest and utility. This gives a certain diffuseness to the
discussio i but adds life to it.
The chapter on drug plant cultivation is a somewhat novel dis
cussion in a work of this type, but thoroughly justifiable, since drug
plants must be grown by man's aid sooner or later if medicine is
not to lose agents valuable for combatting disease. The author
would have done well had be indicated that he used the term culti
vation in a somewhat elastic sense. A reader might receive the
impression that the long list of plants cited as now under cultivation
in the United States were to be obtained in this country in com
mercial quantities for drug purposes. The fact that a plant is being
grown experimentally in a garden should not lead one to think that
an agricultural industry has been established. As a matter of fact
not a dozen of our wild drugs are now under cultivation in this com
mercial sense. The question of what sorts may be capable of culti
vation in this sense, depends for its answer on many factors at
present not known. The writer, however, is clearly an optimist in
his view of what the future can be expected to do.
The subject of pharmacognosy is bounded by varying lines of
latitude, according to the author who defines it. Lying, as phar
macognosy does, at the meeting point of several relatively distinct
sciences, it is easy for the enthusiastic pharmacognosist to seek to
extend his sphere of influence somewhat widely over his neighbor's
domains. Acting on this principle Fliickiger has enriched the litera
ture of this science with a series of interesting and instructive studies
which might be claimed by his historical colleagues as fairly within
their realm. This way of looking at pharmacognosy is most stim
ulating to a man who has a liking for a broad sweep but it has
practical disadvantages when so considered by the teacher. If a
subject is to ''teach well" the clearer cut the outlines may be and
the more definitely the problems may be limited, the easier for the
teacher, especially for one who works under pressure of short time
for his subject and who hears the call for practically "useful" in
struction. The chapters on pharmacognosy are written from the
latter standpoint and will form a most valuable aid to the teacher.
The illustrations are good and well chosen. The same commendation
may be made of the chapters dealing with powdered drugs and
foods. The utility of the key could be judged only after a prolonged
test, but it is fair to presume that it is the outgrowth of consider
able successful experience. Since the subject of powdered articles has
become an increasingly important line of practical investigation
under the operation of the pure food and drug laws, this feature of
the book will be very useful to students seeking to prepare them
selves for the public service in this direction.
Taken as a whole, the book can be strongly recommended and
should go far in meeting the desires of teachers of pharmaceutical
botany and pharmacognosy. It is apparently meeting with a very
active appreciation since this is the third edition in the rather short
life of the book. Rodney H. True.
Hydrastis Canadensis. Facsimile reprint and illustrations of the

article in "Drugs and Medicines of North America" 1884. Bul
letin of the Lloyd Library of Botany, Pharmacy and Materia
Medica. Reproduction Series No. 6. By J. U. & C. G. Lloyd.
One vol., pp. 76—184. 1908.
Students of North American drugs are greatly indebted to the
Lloyd Library for the five numbers of the reproduction series that
have appeared thus far. The first number which appeared in 1900
made generally available Barton's "Collections for an essay toward
a materia medica of the United States," originally published in 1798
and 1804, The second number, published in 1901 made known to
modern students 'TThe Indian doctor's dispensatory" a veritable
curiosity of our pharmacographia amerkana. The year 1903 gave
us the "Materia medica americana" (1787) of the German physician
Johann David Schoff who had come to this country as surgeon of
the Hessian troops who fought for England against our ancestors.
The same year also placed at our convenience Cutler's "An account
of some of the vegetable productions naturally growing in this port
of America" : the original of which antedated Schoff's 'Materia medica'

by two years. After a lapse of about four years, Bulletin No. 5 of
the Reproduction Series gave us the reprints of three publications,
viz. "An investigation of the properties of the Sanguinaria cana-
dnesis; or Puccoon" (1803) by Wm. Downey of Maryland: "Travels
through the interior parts of North America in the years 1 700, 1767
and 170N" by Captain J.Carver, first published in London in 1778;
and "Libellus de usu medico Pulsatillae nigricantis'' by Antonius
Sttirek which emanated from a Viennse press in 1771.
After such an array of old timers, one is well nigh dumbfounded
that as No. 6, there should be reproduced a chapter of "Drugs and
Medicines in North America ' which publication appeared in fascicles
when some of us, who are still inclined to regard ourselves as young,
first took an interest in matters pharmaceutical. Yet there appears
to be a cause that justifies so unusual a procedure. From a drug
' then only of Eclectic importance," Hydrastis canadensis has become
a matter of concern to those who are confronted with the necessity
of purchasing large quantities of this drug that is rapidly disappear
ing from our forests and which has thus far at least baffled many
a person who has attempted its cultivation. Pharmaccutical history
seems to be making rapidly in these days of strenuous life. At a
time when the nation has just awakened to the necessity of preserv
ing our natural resources, we may well reflect upon the statement
(p. 91) that "one lot of eight thousand pounds sold in Cincinnati in
1880 at four cents." To this may be added the foot note, viz.
"From 200 to 250 roots of dry hydrastis are required to make one
pound," in order to appreciate how many plants were removed from
the soil without putting back a single bud for the purpose of pro
pagation.
No doubt, this bulletin meets a demand, although it will be less
sought by the historical student, just at present, than by those whose
interests in this important drug are of a different nature. E. K.
A Compend of Pharmacy, by Dr. F. E. Stewar't. Seventh Edition.
Revised in accordance with the additions and corrections made
in the U. S. P. to comply with the new food and drug act,
1907. One vol., pp. 187. P. Blakeston's Son & Company,
Philadelphia, 1908. fl.00 net.
This "quiz compend," based upon Raaiington's "Text Book of
"Pharmacy'' and the U. S. P., has for its object, the author tells us,
"to present information concerning. official products and preparations

in such clear, concise, and condensed form as to be of special ser
vice to the student in memorizing it" and to enable him "to pass
the examination before him in a creditable manner." But it is not
intended, he also informs us, to be put into the hands of students,
or drug clerks desiring to pass examining boards, to serve for the
purpose of cramming: neither is it "adapted to nor intended for
conducting students across lot."
After reading the above rather contradictory statements, and
looking through the table of contents one wonders just what the
author's idea of a short cut may be; for the book, though very
good in its way, impresses one as an extremely short cut. How
ever, so long as state board examinations are conducted an they
are at present, and the candidate is required to know for the
occasion a multitude of unrelated facts and isolated data, which he
does not expect and no one expects him to remember, short cuts to
pharmacy will be in vogue and quiz-com pends will remain in demand.
As such a compilation, the book under consideration has much to
recommend it and, probably, as little to condemn it as any quiz-
compend could have. It is not a collection of questions and answers
selected from the lists of examining boards, but a compilation of
data, crowding into less than two-hundred small pages information
concerning not only the whole realm of pharmacy; but much of
physics, chemistry and materia medica as well. Used by the student
as a brief review before his examination, it might furnish a complete,
connected oversight of the subject in a very short time; but used
for memorizing by one who has not had a thorough, careful, system
atic course of pharmaceutical training, it would be a means of ob
taining information without understanding, and as such cannot be
too strongly censured. N. Wakeman.
Trait fc Pratiqe D'Analyse Des Denrees Alimentaires par E.
Gerard, professeur de pliarmacie et de pharmacologic a
rUniversite" de Lille et A. Bonn, directeur du laboratoire
municipal de la ville de Lille. — Vigot Freres, Editeurs, Paris,
1908. Uu volume in —8° raisin cartonne avec 41 figures,
15 fr.
For the proper understanding of the purpose of this book it
should be said that the French law on food adulteration provides
that four samples of each suspected food product be procured, of
which one is to be analysed at the administrative laboratory accord

ing to the official methods; in case of a contest two more samples
are analysed by opposing experts, who may at their option work
together or separately and who are at liberty to employ whatever
methods they may choose; the fourth sample is to be used by still
another expert in case of disagreement between the other two. The
question of the merit of such a proceedure need not concern us here.
The volume before us contains the French food laws and regula
tions as well as the official methods of analysis in an appendix, but
the work deals mainly with unofficial methods of analysis, of which
a large number are given, and to a lesser extent with the composi
tion of natural and of manufactured food products, the adulterations
commonly employed, and other information of value to the analyst
in interpreting his results and of service to him on the witness
stand. The statement of the authors in the preface that all the
methods given can be used in the laboratory of the pharmacist who
may be appointed as expert by the tribunal or the court of appeals,
presupposes not only a greater knowledge of the subject but also a
vastly better equipment on the part of the French pharmacist than
is possessed by the great majority of his American confreres.
The most important subjects discussed are wine, beer, brandy
and other beverages, edible fats and oils, dairy products, coffee, tea
and cocoa, sugar and other saccharine foods, spices and condiments,
meat and meat products, water, canned goods and chemical preser
vatives. Most of these subjects are quite exhaustively treated and
reference to recent forms of adulteration shows that the book is
quite up to date. Many of the analytical methods are not mentioned
in American or English treatises on food adulteration and should
therefore be of special interest to the food chemists of this country.
Richard Fischer.
The New Standard Formulary. Volume I: Pharmaceutical pre.
parations, comprising all preparations official or included in
the pharmacopoeias, dispensatories or formularies of the
world, together with a vast collection from other sources, the
whole embracing the entire field of pharmaceutical preparations
as related to all schools of medical practice. By A. Emil
Hiss and Albert E. Ebert. One vol., pp. 576, G. P. En
gelhard & Company, Chicago. 1908.
The title of this volume certainly promises much and the Intro
duction would seem to hint at even more if this were possible. The
writer is not in the least inclined to question the author's word and,
therefore, has not taken the trouble to test the accuracy of his
statement by checking up the preparations of the numerous author
ities suggested on the title page and enumerated in the Introduction.
It would seem that such a collection, including formulas from
all of the European countries that have contributed largely to our
cosmopolitan population, ought to prove of great value to American
pharmacists, more particularly to those who are located in those
sections of our larger cities which have a miscellaneous foreign po
pulation.
A general review of a formulary is an unsatisfactory undertaking
at best, and a detailed criticism is out of the question. If all books
must prove their merits by actual use and trial, this is especially
true of formularies. The pharmacists of the United States, not the
book critic, are the court of last resort that passes judgment on a
book of this sort. That they have not condemned it becomes ap
parent from the growth of the original formulary of Ebert and Hiss
into a several volume work. In its present form it will, no doubt,
be even more acceptable to the pharmaceutical practitioner than in
its first conception.
The volume is crowded with a host of practical data and is pro
vided with what appears to be a good index. It would, however,
have come nearer the ideal of such a formulary had it been provided
with a better synonymy in all of the languages represented by form
ulas. If a pharmacist finds on a slip of paper a popular synonym
in German, Norwegian or some other foreign language, the formula
may do him no good, because he does not know which one to look for.
He will, therefore, have to resort to books on synonj*ms or to the
indexes of his dispensatories. No doubt, if this deficiency should
prove serious, the next edition of "The new standard formulary"
will supply it. E. K.
Jahresbericht der Pharmazie, herausgegeben vom Deutschen Apo-
thekerverein. Bearbeitet von Dr. Heinr. Beckurts, unter
Mitwirkung von Dr. H. Frerichs und Dr. H. Emde. 42.
Jahrgang, 1907. (Der ganzen Reihe 67. Jahrgang.) Ein Bd.,
pp. IV, 608. Vandenhoeck und Ruprecht, Goettingen,
1908. M. 19.00 geheftet, M. 20.00 gebunden.
Abstracts of several thousand articles crowded into a compact
volume represent the scientific literature published during the year

1!)07, which is supposed to be of interest to the pharmacist. How
ever one is struck not so much by the wealth of information as by
the diversity of the literature. Plant chemistry and other botanical
and biological subjects, general and pharmaceutical chemistry, even
new remedies, all come in for their share of consideration. But the
German pharmacist with his university education is supposed to
have broader interests. Medical chemistry and the chemistry of
foodstuffs and beverages make up a very respectable portion of the
volume.
In a casual perusal of the volume, the eye is arrested at a num
ber of places. One becomes interested in the chemical and pharma
cological studies of ginseng. The use of ginseng by the Chinese has
so long been regarded as little more than an Oriental superstition
for which the "brother Chinese" was to be pitied and possibly ex
ploited by his more advanced christian brother that we look with
some skepticism upon the discovery of glucosidal and alkaloidal
substances. The name of one of the investigators incidentally re
minds us pf the fact that the Orient is awakening in matters scien
tific as well as commercial.
Our own country, although we well know of its increased scien
tific activities, scarcely can be said to be formost either in number
of contributions or quality of work. It appears to be best repre
sented in the chapter on new remedies and specialties. Even here it
is not the synthetic new remedy that stunds forth, but the private
formula. The elegance of our proprietary preparations may pave
a way for their sale even in foreign countries and thus bring about
a commercial supremacy as they are indicative of a certain suprem
acy in the art of pharmacy, but scientifically we still have great
strides to make before we shall have caught up to some of our
European colleagues on the continent.
That a complete set of the "Jahresbericht is not yet to be found
on the shelves of each and every library of the seventy odd pharma
ceutical schools and colleges of this country, argues against these
institutions, not against the German annual. Let us hope that
when the American Conference of Pharmaceutical Faculties celebrates
its first quarter centennial, this can no longer be said of our educa
tional institutions. E. K.
' "ML LIBRARY,'
Ui\iV. up MJCH.
0EC88K»t
Vol. 20. DECEMBER, 1908. No. I2.
Founded in 1882 by
DR. FREDERICK: HOFFMANN.
Edited by
DR. EDWARD KREMERS
WITH THE CO-OPEbATION OF

Or. Dasikl Base, Professor ol Chemistry, Prof. J. U. Lloyd, Professor of Chemistry
University of Maryland, Department of Cincinnati Eclectic Medical Institute, and
Pharmacy, Baltimore. Pharmaceutical Manufacturer.
Prof. J. H. Bf.al, Professor of Applied Phar
macy, Pittsburg College of Pharmacy. Dr. A. B. Lyoss, Pharmaceutical Chemist,
Detroit. Mich.
Prof. I. W, Braspel, Assistant Professor of
Pharmacy, University of Washington. Mr. Harry B. Masos, Associate Editor Bul
Dr. Cbarllb E. Caspari, Professor of Chem letin of Pharmacy, Detroit, Mich.
istry and Physics, St. Louis College of Dr. F. B. Power, Director of the Wellcome
Pharmacy. Research Laboratories, London, England.
Dr. Virgil Coblestz, Professor of Chemist Prof.W. A. Pccener, Professor of Chemistry,
ry and Physics. New York College of Phar University of Illinois School of Pharmacy.
macy.
Dr. R. Fiscber, Assistant Professor of Prac Dr. J. O. Scblotterbece, Professor of
tical Pharmacy, University of Wisconsin. Pharmacognosy, University of Michigan.
Dr. H. M. Gordis, Professor of Organic Prof. A. B. Stevess, Professor of Pharmacy,
Chemistry and Drug Assaying. North University of Michigan.
western University School of Pharmacy,
Chicago. Dr. It. H. True, Physiologist in charge of
Dr. H. Kraemer, Professor of Botany and Drugs and Medicinal Plants, Bureau of
Pharmacognosy, Philadelphia College of Plant Industry, Department of Agri
Pharmacy. culture, Washington, D. C.
Published by PHARMACEUTICAL REVIEW PUBl. CO., MILWAUKEE, WIS.

TABLE OF CONTENTS.
Prei'lpltatod Sulphur. By ff. M. Sorley H5H The Volatile OIIH: 1901 to T9(W. By t. ft.
The Apothecary, a literary study. By Ed. Rrandel *
Kremers a57 Literary - —
Thymoqulnone and Hydrothymoquinoiu'.
By .Y<.//(e Wakenmn .'I'll
Subscription Prica Par Year:

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Schieffelin & Co.

Importent, Exporters, Jobbers and Manufacturers of
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Imported and Indigenous Drugs, Staple Chemicals. Foreign and
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Sponges; Druggists' Sundries, Novelties and Fancy Goods.
* PURE DRUGS >«

Manufacturers of
Standard Pharmaceutical Preparations
Including Fluid and Solid Extracts, Elixirs, Syrups, Ulntments,
Hypodermic and Compressed Tablets and
SOLUBLE COATED PILLS
Comprising all the Official rills of the Pharmacopoeia
Unequaletl in regard to Purity of Composition,
Solubility of Coating, Uniformity in Size,
it ml Perfection of Form mid Finish.
PHARMACEUTICAL HE VIK H".
ESSENTIAL OILS
Absolute Purity Highest Standard
Pounded 1820.
Anethol,
THERE IS an unquestioned Citral,
satisfaction in originating and mote Eugenol,
especially so when the tesul/ant has Pure
Encalyptol,
proven of pzactical utility.
Geraniol,
Safrol,
WE NAME on the margin a Synthetic
few, of the many, zelated products. Cinnamic
Aldehyde.
■ SPECIALTIES.
POLLANTIN Dunbar's Serum Treatment of HAY FEVER

OIL OF CYPRESS External Treatment of WHOOPING COUGH
OIL OF ATLAS CEDAR WOOD (Libanol Boisse)
Send for descriptive literature.
FRITZSCHE BROTHERS,
82—84 Beekman Street, NEW YORK.

Fairbanks Scales
will show you whether you
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= OVER 700 'PATTERNS. =
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Is one-third smaller than any other camera
for 2V\ i1/\ pictures.
Manipulation is the simplest, equipment
the most complete.
Loads in daylight, taking tvjet've films Fairbanks, Morse & Co.
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Weighs but eleven ounces, costs but X5.0O.
That's the storv in a nutshell. . j
Rochester Optical Company,
Rochester, N. Y. fcLSSfl Wanted.
"Pharmaceutische Rundschau."
Vol. 2, Nos. 5 & 10.
" 3, Nos. 10 & 11.
Special Attention. " 6, No. 2.
" 9, No. 8.
The right way to buy a drug store " 10, No. 3.
— to sell one — to get a position or help " 11, No. 8.
whether in U. S. or Canada is to write "Pharmaceutical Review."
to F. Y. KNIEST, H. P., "The Drug
Store Man," N. Y. L. Bid., OMAHA, Vol. 18, No. 1.
Nebr., U. S. A. Estab. 1 904 — Strictly Offers should be made directly to C.
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waukee, Wis.
WHITE METAL GOODS for Dra^sts
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Pharmacists, Perfumers etc. Descriptive Wanted.
Catalogue mailed on application. The following numbers of the Phar
A. H. WIRZ, maceutische Rundschau, viz. :
913-917 Cherry St., 1887, No. 2, and
PHILADELPHIA, PA. 1892, Nos. 1, 3 & 10
are wanted by the College of Physicians.
Offers should be addressed to Librarian
goncentratlonen oder Reslnoide. CHAS. PERRY FISCHER, 13th & Locust
Sts., Philadelphia, Pa.
Unsere Firma gehort zu den ersten und
ftltesten, welche diese Klasse von Prodncten
vou cmerikauischen Urogen eingefiihrt haben Wanted. South, Slx (food salesmen in the
West and Middle
und im groasten Massstabe fabriciren. West to handle (either ei-
eluslvely or as a side line) a first class line of
Correspondenz wird erbeten und jede Druggists Labels & lioxes for an old established,
well known and reliable house. Would not enter-
tain an application for Bide line proposition un
A1iskunft iiber die Producte unserer Fabrrk less you are calling on Druggists and have ample
sowie iiber amerikanische Drogen wird bereit- time to work our line thoroughiy in each town
willigst ertheilt. and city in your territory. Men "with a practical
knowledge of the Drug business preferred. Liberal
commissions. Address H 32 % Lord 8c Thomas,
LLOVI) BROTHERS, Cincinnati, 0., U. S. A. Chicago, 111.
- 130 -
PHARMACEUTICAL RE VIE W.
Latest Additions to the List of
...BAYER Pharmaceutical Products...
We are sending to the physicians throughout the United States the literature
and samples of
SAJODIN EUMYDHIN
Agreeable Iodine Medication The New Atropin Derivative
ALYPIN ISOPRAL
The New Local Anesthetic The Improved Chloral Hydrate
IOTHION VERONAL
The Local Succedaneum for the Iodides The Most Approved Hypnotic
You will have calls for them. Order a supply from your Jobber.
Write for literature to

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REMINGTON'S SPECIALTIES
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A simple, accurate and durable
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private formulae.
Large Capsule Fillers for Manu
facturing Purposes.
Write for circulars of Capsule Fil
ler and other specialties to
Remington Mfg. Co.

514 Arch Street
PHILADELPHIA, PA.
— 187 —
PHARMACEUTICAL HE VIE II'.
This excellent cough syrup is a distinct favorite with the med

ical profession—in fact, few medicinal preparations have so
wide a vogue during the season of coughs and colds. It
couldn't well be otherwise. SYRUP COCILLANA COM
POUND is a capital agent from a therapeutic standpoint.
It is elegant pharmaceutically. It does not constipate—on
the contrary, it is slightly laxative. It is highly agreeable
to the palate. We are again pushing it aggressively among
the doctors. Order SYRUP COCILLANA COMPOUND
now ! .J
Pint and 5-pint bottles.
EGG EMULSION COD LIVER OIL, IMPROVED-40% cod

liver oil emulsified with eggs and brandy. Pint bottles.
EMULSION COD LIVER OIL, IMPROVED, WITH
HYPOPHOSPHITES-40^ cod-liver oiL Pint
and 5-pint bottles.
EGMOL-Olive oil (40%) emulsified with
eggs and brandy. Serviceable in wast
ing diseases. Pint, 5-pint and gallon
bottles.
NUTROLE—Animal and vegetable oils
(40f>) emulsified with eggs and
brandy. Useful in general debility.
Pint bottles.
These are efficient nutrients. They
are palatable. They are favorites with
medical practitioners. They yield
good profits to the retailer.
Send along your order!
PARKE, DAVIS & COMPANY

Laboratories: Detroit, Mich., U.S.A.; Walkerville, Ont.; Houmlow. Eng.
Branches: New York, Chicago, St. Louis, Boston, Baltimore, New Orleans, Kansas City, Min
neapolis; London, Eng.; Montreal, Que.; Sydney, N.S.W.; St. Petersburg, Russia;
Bombay, India; Tokio, Japan; Buenos Aires, Argentina.
PIfA KMACE UTICaL RE VIE IV.
Specify MERCK'S
* on your orders for '
CODEINE SULPHATE
because
MERCK'S dissolves almost insta.ntaLneovisly
Good Customers
Notice to the trade
People who buy Zymole Trokeys are

a good sort of customers — the sort who (ACotice is hereby given that the contract
believe in having the little luxuries. heretofore existing between The R. Hardesty
So, when we persuade such a person Mfg. Co. and Samuel T. Hensel of Denver,
he needs Zymole Trokeys, and you get Colo., entered into under date of May 4th,
him to buy them from you, why, you've '04, for the purpose of the manufacture of
a fair start towards selling him other pay The Hensel Syrup Percolator, was annulled
ing things, besides.
and cancelled on August 1 7th, '08.
Just to insure everyone's knowing you
havs Zymole Trokeys, it's well to keep In the future The Hensel Syrup Per
them where everyone can see ; and to use colator will be manufactured only by The
the advertising matter we give you. Samuel T. Hensel Mfg. Co. of ^Denver,
Cultivate your Z. T. customers. Get Col.
as many as you can. They're good.
THE SAMUEL T. HENSEL MEG. CO.
By SAMUEL T. HENSEL, Ph. G.,
THE ZYMOLE COMPANY (Inc.)
NEW YORK, U. S. A.
99
"M. C. W.
These letters are synonymous with highest purity and reliability when applied to
medicinal chemicals, and constitute the trade mark by which the products of the
MALLINCKRODT CHEMICAL WORKS
are designated. Pharmacists desiring the best goods obtainable at reasonable prices
should allways specify "IM. C. W."
— 139 —
PHARMACEUTICAL SE VIE IV.
PHARMACEUTlCAL REVlEW PUBL CO
TABtE OF CONTENTS AND LIST OF ILLUSTRATIONS

from Bolton's "FOLLIES OF SCIENCE."
Frontispiece. Broslk's "Rudolphe chez Chapter X. Rudolph's Physicians.

son alchimiste." Dr. Michael Mater.
Title-page. From MtisIeum Hermeticum. Preparation of Theriac.
Chapter I. Two Enghsh Adventurers. Paracelsus.
Queen Elizabeth. Preparation of Gualnc Re
u Dp. John
II. The Dee. of Bohemia.
Solomon medies and their Admi
nistration.
Bridge of Curl IV, and the KathiiauH, Prague.
Hra.dschin, Prague. *' XI. The Rudolphine Academy
The Cathedral of St. Velt. of Medicine.
" III. Gold Alley, Prague. Materia Medica.
Tenter's Alchemist. A Pharmacy tu XVI. Cen
Birth of the Philosopher's tury.
Stone. " XII. Fortunes and Misfortunes.
" IV. Rudolph and Doctor Dee. Kingly Gold and Queenly
ITudolph II, German Em Sliver.
peror. Michael Sendlvoglus.
Dr. Dee's Shew Stone. " XIII. The Secret Symbols of
A Successful Transmuta Pontanus' Letter.
tion. Distilling Apparatus.
Chapter V. Rudolph and the "Golden A n Alchemist's Labora

Knight:' tory.
Edward Kelley, the "Gol Key to Symbols.
den Knight." Chapter XIV. A Tragedy in the Royal
Kelley's Horoscope. Mens.
" VI. Rudolph's Art- Treasures. A Pharmacy in XVI. Cen
The Ilradschin, Prague. tury.
German Hall. XV. Rudolph's Dream.
VII. Seeking the Philosophers' Theosophic Emblem.
Stone. XVI. Magic and Sorcery.
Augustus of Saxony. Heurrlcusl ornelfuH Agrippa
Iêonhard Thurnelsser. Astrology, Alchemy and
VIII. The Man with the Silver Magic.
Sose. XVII. Rudolph at Work.
Uranlborg. Teyn K irehe.
The Belvedere. XVIII. Rudolph's Sovereign tyand
MonumenttoTycho Brahe. Death. r
** IX. Astronomical Wisdom and Kudolph II. ^
Astrological Polly. XIX. Decline of the Follies of
John Kepler. Science.
— 14o -
PHARMACEUTICAL RE VIEW.
PHARMACEUTlCAL REVlEW PUBL CO.
MONOGRAPHS
1. Popular German Names. This popular pamphlet has been revised

twice by its author, Dr. Fr. Hoffmann. 0.50
2. Reagents and Reactions known by the names of their authors.
Based on the original collection of A. Schneider; revised and en
larged by Dr. Julius Altschul; translated from the Gorman by Dr.
Richard Fischer, Asst. Professor of Practical Pharmacy at the
University of Wisconsin. Although imperfect in many respects, this
compilation has proven a convenient aid in the laboratory and on
the desk. A revision is now in progress. Out of print.
3. Popular Scandinavian Names. A compilation of popular Swedish
names of drugs and medicines by Harold Bruun, with formulas for
the preparation of a number of galenicals not generally found in
American reference works. This list is also being revised. Copies still
on hand can be had for $0.15
4. Early Phases in the Development of Pharmaceutical Legis
lation in Wisconsin. An account by Edward Kremers of the evolu
tion of the first local pharmacy law in Wisconsin with the documents
on which the account is based. Pamphlet, pp. 43. $0.50
5. Some Cuban Medical Plants. While collecting plants in Cuba
during I he year 1895 and 1896, Prof. R. Combs had his attention
directed to numerous plants of the island used as domestic remedies.
Pamphlet, pp. 20. $0.15
6. History of the Art of Distillation and of Distilling Appara
tus. By Oswald Schreiner. Pamphlet, pp. 59, with 65 illustrations.
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7. The Crude Drugs and Chemicals of the United States Phar
macopoeia (1890) and the Preparations Into Which They
Knter. Bv W. O. Richtmann. Pamphlet, pp. 55. Now being revised.
$0.25
8. Progress in Alkaloidal Chemistry, 1903. A collection of ab
stracts by H. M. Gordin. Pamphlet, pp. 40. $0.30
9. The Sesquiterpenes. A monograph bv Oswald Schreiner. Brochure,
pp. 130. $1.00
10. Progress in Alkaloidal Chemistry for 1904. By H. M. Gordin.
Brochure, pp. 94. " $0.70
11. The Volatile Oils: 1904. By I. W. Brandel. Brochure! pp. 51.
$0.35
12. The Balance. By I. W. Brandel and Edward Kremers. Brochure,
pp. 49, with 48 illustrations. Intended primarily as a text for students.
$0.35
13. A Review of the Literature on the Estimation of Alkaloids
for the Year 1905. By W. A. Puckner. Brochure, pp. 17. $0.20
14. The Naming of Carbon Compounds. By W. A. Puckner.
Brochure, pp. 17. $0.20
— 141 -
PHARMA CE UTICA L RE VIE W.
PHARMACEUTlCAL REVlEW PUBL CO.
MONOGRAPHS. — Continued.
15. Volksbenennnngen der brasilianisehen Pflanzen und Pro-
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pp. 252. 12.00
16. Pintroot and its Substitutions. By W. YV. Stockberger. Bro
chure, pp. 64, with 2 plates and text illustrations. $0.50
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18. The Volatile Oils: 1905. By Braudel. Brochure,
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21. Plant Pigments. By I. W. Braudel. Brochure, pp. 72. $0.60
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This is a reproduction of a library book that was digitized

by Google as part of an ongoing effort to preserve the

VOLUMK 2<i. JANUARY, 1908. Number 1 .

German Pharmaceutical Institutes.

I. Pharmaceutical Institutes of the University of Berlin.

Laboratory for Qualitative Analysis.

these institutes should be contemporaneous with the advanced

for the tendency toward commercialization has made itself felt in

response on the part of the government to the continued demands

how much more surprising is it to contemplate the fact that the

recalls the fact that the first professor of chemistry, M. H. Klaproth,

pharmaceutical 'education at Berlin reads like an old story. The

following scientists: the first assistant Prof. Dr. Traube, the

These articles have been collected in the "Arbeiten aus dem

Botanical Garden at Dahlem. The instructional vulue of such a

Progress in Alkaloidal Chemistry during the Year 1906.'

Itv //. .1/. Gnrdm.

The octohydrometanicotine is identical with the octohydronicotine

Octohydrometanicotine, f'loHaaNa, is a colorless oil boiling nb

or bromomorphide previously obtained by Schryver and Lees (J.

morphimethine, C1gH2sNOaClg, is formed which when decomposed

On treating bromocodide with ethyl mercaptan and sodium in

Like phenanthrene, 'the trioxyphenanthrene is easily converted

14. Pharmaceutical Notes from Nuttall's Journal of Travels into

reading, the writer was greatly disappointed in one particular. He

interest: "The sweet gum tree (Liquidambar styraciflua) , which

Assay of Fluidextract of Belladonna Leaves.

The pharmacopoeial process for the assay of fluidextracts of the

soltition from the amount consumed in the first blank experiment.

documentary. It may be regarded as a trifling matter that the

Mt'SEUM Report. A series of notes on donations to the Museum

A Manual of Materia Medica, especially designed for students of

this arrangement is very satisfactory and instructive, but when

Phaumaknostischeb Phaktikum. Kine Einleitung zur mikroskopischen

In the former book but 37 drug powders were discussed, in the

Manual of Physiological and Clinical Chemistry, by E. H.

Even so heterogeneous a combination of physics, chemistry, clinical

MeDIZINISCH-CHEMISCHE I'.NTERSUCHUNGEX FUR APOTHEKER, VOI1 Dr.

thorough detail, with an example to illustrate the method of cal

An Introduction to Vegetable Physiology. By J. Reynolds

Progress in Alkaloidal Chemistry during the Year 1906*

properties of the compound would seem to indicate that it is not

methyldiacetyltrioxyphenanthrene to the quinone. Hence this OH

atoms which form the "bridge" in the phenanthrene molecule must

decomposing the nitrosamine with hydrochloric acid and distilling

The amount of potassium permanganate consumed in this reac

The 5-nitrouracyl was prepard from methyluracyl by the method

alcohol but insoluble in ether. It forms a hydrochloride, a hydro-

hydroxy derivatives of flavone. Kaempherid is a methyl ether of

other cases which might be mentioned would indicate the possibility

" Journ. Chem. Soc.. 81, p. 585.

which is a methyl ether of quercetin, both have two hydroxy groups

Braziline obtained from Brazil wood and haematoxyline obtained

They are obtained by the oxidation of the hydrocarbons fluoranthene

Under the degree of saturation CnQan—a«, 2-naphtyl-naphtoqui-

By /. W. Branilel and Ed. Kremers.

Fig. 36. Automatic Repercolator.

Fig. 38. Percolator, improved foi

A device to avoid the inconvenience of

Fig. 40. Syphon percolator.

The Volatile Oils: 1901 to 1903*

. Cathelineau and Haussera4* recommend the following method for

41. Oil of Savin. G.-H.-K., p. 272.

hydrochloric acid, led Fromm42 to offer the following formula for