vy) MERCK 1B DD DD. ¢ FIFTEENTH EDITION RSC PublishingAN ENCYCLOPEDIA OF CHEMICALS, DRUGS, AND BIOLOGICALS FIFTEENTH EDITION Maryadele J. O'Neil, Editor-in-Chief Patricia E. Heckelman, Senior Associate Editor Peter H. Dobbelaar, Associate Editor Kristin J. Roman, Assistant Editor Catherine M. Kenny, Senior Editorial Assistant Linda S. Karaffa, Technical Assistant Published by The Royal Society of Chemistry 2013advancing the chemical sciences. Supported by 4 The RSC is the largest organisation in Europe for tivities span education worldwide network of members and an intemational publishing business, our & conferences, science policy and the promotion of chemistry to the public. Our 47,500 members come from diverse areas of the chemical sciences and enjoy acess 10 scientiig information, careers advice and a wide range of exclusive benefits. 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Benny in i: by MS: idem er al sriical experience in cohithohong 05 ct ety ean eet meni baer gp Bical incisions: Gy E- Amieterof decent TE 483 (1999), Clinical evaluation it fol Tr ge Miteplaay: Ny pseu Oratars Sere 89 (985) in nag ee 198 cane Greenwald era eh Gastroenterol 98 1982 (2003), Review of biomedical applications © Vor Res, $8, 519-548 Gan), Pie acid NMEA. torn, gg n> Aci butyl eae ry Polym, Sci. 19, and nanoy closure of Wer eral, Adv. Drug Deter Colorless tiguid. bp, 68 Sire sive Compound 1.4410. Insol in water Flash 9t, closed cup: fase ee nie JG800), Vapor ce ep: eezitry Ni sD rs ter and SIA dynestm. Highly veace sik we —— ee Paya | 2-cyanoacrylate). traden = aa Polymer.” (25154-80-7] Poly(outy! Seale Caren ce articles as pharme a USE: Adhesive. Polymer nanosar Goat orca rug dhvery TuERAP CAT: Thsue athesig ‘THERAP CAT (VET): Tissue adhesive, ‘Therapeutic category (eternary 40,989. ni? 1.442. Physical data for tile compoundAspoxicillin we. och, Neclles oF prisms fom benzene. mp 156-161 cesta tne: sy ne {alae in Tigroin than pseudouspitins mp Neg, Mins Practialy inst in NasCOr sola? NO THVAAPCAT: Anthclmintc(Cestnden, rely clin ae bensene Less Solin NOH 0 Aspiiom, sale fr mle sie sheen: ima BP) ize and ies of Dryers femes Coa ea SS connt: Picconl temple os tare ea ficin mare, ic rerein, hycs wet ie taese ash ‘ere Aspidlm, Okorsinot mle em. Ancer ee thick iy. usually depositing a granu, crystsbstane, Biter ae peat tste dot Fess than 10. foe in water Paty col cob or ehlorfonn. Amon! completely so i ether; mot es hag Asien in preter. Shale nel! before pening serar Car, Amtelininic (Ceres) TUIEAEAT (VET: Amteminic (Cestodes), 89, Aspidosperma, Quebracho, Dred bark of Aspid sperma guebrath lane SchleeM,Apcynaceae, Hat. Argon ih Cony 02-14% alkalonds—aephonpermine, aspiosperna tins, aspiosamine, quctrachine,qushrachatnne,hypoquctrshine, svt qucbrach tannin sr, Chorin quctvacho canbe used Wo conta nematodes and ‘Santnyer, US 3799612 (1957 to Mons Minkarent: Respirstrystinulan 4). Aspidaspermine. (466-49. 1-Aceiyl 17 methoxsas: piknpamidine, Coll NOsmalvt 35449. C74 54% HR 3, Kirin. © 9.08%. Ih Aspidasperma gucracho-blanco Schl. Tats ic hota Ry & Pav and Vallesia glabra (Ca.) Link, pognaceae, (Frau, Ber A, 2189 (1878), Hesse, An. 21 Mo isi), Eins. Chem Sor, 108, 2738 (1914); Deoeu ea Iu TOO, OSI: Holker eral, Org. Chem. 24.314 1989) Sine tre: |Cinwoy ef aly Tetrahedron Lett 0. 1 4 (1959). Crystal Sirus Mils, Nyburg. J. Chem. Sor 1960, 1858, Stercochemis Ay. Smuh, Wrobel, sh 1463; Craven, Zachatas, Experientia 24, Tho Adak). Biogenesis, Robinson, Tetrahedron Leto. 18. 1F8 {1950}, Syihess of dorm Stork Doin J Am. Chem. So. BS, Sena (ise) Ran ol, evsahedron Lert 1968, 226; Stevens et Go), Chan Commun, 1971, 887; . F. Manin ea J. Am. Chem Soe 102 5304 (1080). Aspidonpermine has been repr ashing 2 ide viet of pharmacologic! properties. ncldng diuretic and Tepiay stimulant act Biologteal and phytochemical val thin RL Lyon eral. Pharm. Sci 62, 218.1973), Mirobial rao ‘ral id 4, 2021 (1975). SMR stay WE Canpeler al, Spectnose. Ltt 26, 707 1983). ol: HF. Deutsch etal, J. Phovm Biomed. Anal 2, 1283 (1994). Acute tonicity ata, Plak, J Doul, Further Swe of Compounds for Radia Protectan (ADA91390, USAF Radiation Lab, 196%) 82 ®. oak Needles or prisms frm al, ees from pet eet, mp 208 Sablimes UA tp, 220" ff) 10.2" tae [ay 9" (hor Consult the Name Index before using this section a2 form), wv max methanol): 218,255, 280-290 nm (log 24.52.4084 BE8-340). One pram dissolves 40 ml water, 30 ac. 10) ther Ako soln henzene, chloroform, pet ether. LD ip in mie Omak Pirak Dou. [N-Formsl-N-deaceslaspidospermine, Vallesine, Co) My.N (0, Stricture: Taylor eral Hehe Chim, Acta AZ, 2780 (1559) Ln. fine needles from actone mp ISL 156°, [alt 91 #210 [E814 ipabe ale) sv mane 211, 250m (og e447. 394) B41. Aspirin, (50-78-2) 24 Acciyloxy)benzoi ai al elie acid acetate; Pactons benzoic ai aces aise aid: ASE pro, Canoaspnn: Cankpr Cone prin: Angetes: Asta CGaragine: Econ: Empirns Encaprn: Rol: Sop. Cy #hOx rol st 18016. C ANIM. H S48, 0 38825, Prop: C. Ger snhydrde: Fah, Kever& Clar s Industria Chemical. A La nheim, M.K. Moran. Eds, (Wiley nescence. New York th WPS) pp 19-120. Ciystaliation from acetone Hamer. Philp US 2800240 (1959 9p Monsanta)_ Novel proves valving dist a thon Elid. US 824S8R8 (1966 to Norwich Pha) Crystal Strctres Bul Wheatley. 7 Chem, Sor (Sapp) 1968, 6086, Char ‘terization of second polymoepc Tarn. Vishweshwar Pim Chem, Sue 137 10802 3008), Tonsty data ER Har Pharmacol Exp Ther 9, 208 (1947), Evaluation sa isk fctn it Reye's syndromes Poh Walnut af Jam. Med: Assoc. 247, Hao (18D, Review of cline ris in prevention of myocanal Infarction and okey PC. Elwonsl, Drage 28, 1-8 (1980) Sy ina as in prevention of colorectal ence RS Sander et Ch No Bh J. Med. 348,883 (2003), JA. Baron er al Comprehensive desertion, K- Hey. Anal Profle Drag Subs. 8 161999). Monographs Mel. H. Smith K. Sith, The Sole lates Untercince, New York, 1966) 31Spp. Book: Accuaioye ‘ed, HeA.M. Bare ot a, Bas Raven, New York, 1942) 278 po. White monoclinic ables or nese-tike crystals 1.40, yp 138° (rep heating); the met soles at ow max (01 HS: om (484), (CHC) 277 am Uy 68). dress, but ‘moist ait is raualyhydolyed ito salicye and acetic acids ad Iie the odor of acetic aed. Stable i dry ai. pK (257) 3.0 ‘One gram dssoles i 390ml water at 257 10 wae a 3 in'S mi alcohol, 17 ma eloroform, 1015 hl eter. Les soluble m Satya ether, Decomp by boiling water or when dissolved in soln alka ydroxides and carbonates. Inorganic salts of aces {hic aid ae soble in water (exp the Casall), but ate decom ‘Posed ichly. LD orally in mice, rats: 1.1 1 gk (Ha) ‘Gualacol ester, (38882 49.8) Gaacetal Gusti. Cy HO: sol wt 86.28 ‘Methyl ester see Methyl Acetyslieylte Canton: Potential symptoms of overexposere ae increased blocd cating time; nausea, vomiting: iver, kidney injury. Diet contact tnay cause eye, akin and upper respiratory ination, See NIOSH Pocket Gide to Chemical Havards (DHHSINIOSH 97-140, 1997) ‘ “ruRar cat: Analgesi; antipyretic: an thrombote anithrembosie B42. Aspoxilin, (63398-49.6) 2R).N-Methy-D-asparagi- nybN-[(35,SR6R-2-carbory-3,Slimethy LT 0x04 thi Larabie to[3.2 Opt 6-y-2-44hy cons phenselycnamide [0-202 ming 3-¥- meth earbamostropionamide)2-p-hydoss phensl- “cclamiponcinie ack: 28,9 OR) 628-2 [OR}2 ano inchs earhamos ipecpionamide) 24 Aydeoxypheny acetal Salimetiy-Paxe-t this Tazabicyeo[3 2s? carboxy i ack N “mc axparainy ans: ASP: TA. O88, Duy CHG NGOS ml wt 49494, CSL, MISSI, N LID O, Bammatory: an Analgesic: antipyretic: an-inlammators Page 147841. Aspirin. [50-78-2] 2-(Acetyloxy)benzoic acid; sali cylic acid acetate; 2-acetoxybenzoic acid; acetylsalicylic acid: pyrin; Angettes; Asatard; Aspro: Cardioaspirin: Cardiprin: € Claragine; Ecotrin; Empirin; Encaprin; Rhonal; Solprin, CoH,O.i mol wt 180.16. C 60.00%, H 4.48%, O 3: %. Prepn: C. hardt, Ann. 87, 149 (1853). Manuf from salicylic acid and anhydride: Faith, Keyes & Clark's Industrial Chemicals, F. A. Low- enheim, M. K. Moran, Eds. (Wiley-Interscience, New York, 4th ed., 1975) pp 117-120. Crystallization from acetone: Hamer, Phillips, US 2890240 (1959 to Monsanto). Novel process involving distilla- tion: Edmunds, US 3235583 (1966 to Norwich Pharm.). Crystal structure: P. J. Wheatley, J. Chem. Soc. (Suppl.) 1964, 6036. Char- acterization of a second polymorphic form: P. Vishweshwar et al., J. Am. Chem. Soc. 127, 16802 (2005). Toxicity d E.R. Hart, J. | Pharmacol. Exp. Ther, 89, 205 (1947). Evaluation as a risk factor in Reye’s syndrome: P, J. Waldman er al., J. Am. Med. Assoc. 247, 3089 (1982). (Review of clinical trials in prevention of myocardial infarction and stroke: P. C. Elwood, Drugs 28, 1-5 (1984). Sym- posium on aspirin therapy: Am. J. Med. 74, no. 6A, 1-109 (1983). Clinical trials in prevention of colorectal cancer: R. S. Sandler et al., N. Engl. J. Med. 348, 883 (2003); J. A. Baron et al., ibid. 891. Comprehensive description: K. Florey, Anal. Profiles Drug Subs. 8, 1-46 (1979). Monograph: M. J. H. Smith, P. K. Smith, The Salicy- ares (Interscience, New York, 1966) 313 pp. Book: Acetylsalicylic Acid, H. J. M. Barnett et al., Eds. (Raven, New York, 1982) 278 pp. COOH CH, White monoclinic tablets or needle-like crystals. d 1.40. mp 135° | (rapid heating); the melt solidifies at 118°. ‘uv max (0.1N HySO,): 229 nm (Ej, 484); (CHC1,): 277 nm (E}%, 68). Is odorless, but in moist air it is gradually hydrolyzed into salicylic and acetic acids and acquires the odor of acetic acid. Stable in dry air. pK (25°) 3.49, One gram dissolves in 300 ml water at 25°, in 100 ml water at 37°, in 5 ml alcohol, 17 ml chloroform, 10-15 ml ether, Less soluble in anhydr ether. Decomp by boiling water or when dissolved in solns of alkali hydroxides and carbonates. Inorganic salts of acetylsali- cylic acid arg soluble in water (esp the Ca salt, g.v.), but are decom- posed quickly. LDsy orally in mice, rats: 1.1, 1.5 g/kg (Hart). Guaiacol ester. |55482-89-8] Guacetisal; Guaiaspir, CygH 40st mol wt 286.28.