4=-

DocuMENrUNCLASStf lFDUF}NREf RgDtlgrtoN-r'c'f :!+?!'9

F.

;ll}

JOINT

lV1

CTB CONTACTPOINT
@nd ?ESr

JOINT ClB TECHNICAL DATA

SOUR.CEBOOIf
VOLUME

V.

BLISTER, BLOOD, AND CHOKING AGENTS

PART 4. AGENTS HN, O,T, L, AND HL

october

1ee3

-.,noJit{S

U#O[D

,-4"1$r.ffiffiSnu""*
JOINT CONTACT POINT DIRE,CTORATE
U.

Gl.

s"
^u')

S. Armg Dugway Prouing Ground. , utah

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This document may contain
do not
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vhich oo
reproduce legiblY.
Inconsistent page numbers
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DOCUMENT UNCLASS IFIED UPON REPRODUCTION JCP.I, DPG

AD NO,

RDT&EPROIECT 1-M465?ISDO49
TBCOM PROIECT
DPCi REPORT

NO.
NO.

JOINT CB TECHNICAL DATA SOURCE BOOK

voLUME V. BLISTER, BLOOD, AND CHOKING AGENTS
PART 4. AGENTS HN, Q, T, L, AND HL

Prepared by

Don

T.

Parker
Andrew C. Parker

ANDRULIS Research Corporation

660 South 200 East, Suite 418
salr Lake city, uT 84111-3835

October 1993

Project Manager: Kenneth S.K. Chinn

Dirtribution limircd to U.S. Govcrnmcnt rgencig only (Octobcr 1993).

Olhcr rEqucatr murt bc rpfcrrpd to: Commandcr, U,S. Army Dugwey

hoving Grcund, ATTN: STEDP-JCP, Dugury, UT &(n2-5m0

:PPg1l ;,,I)_EEGTOBA, E
.JOhIT'GOtr\ITACT
U;s; aRlvtY DUcwev,inovntc Gnoullo:::
::

:,:,,

&CO-210{49-2r2
DPG/JCP.94/OO2

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.

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pubtic

rtpffino budii td Ua colLEtim ol furrmads b rttnat- lo rfrae[ t lw pa. rqlcra, imluaiE tha tim td ?.Yiawiie irtt ucrid. xrch&! ariilire dttl louc6,
r:ha d.it r.d.d, fi cmCatir! rrrd rditwiE tlr coabsiion ol hl{madm. Sli CmmJltt taef,ditE tt*! brrd.n -timal. d $Y otltr rp.d ol rh.

O.rh.rir{ md m.im.idrE
Hichw.y, Srir. 12O4,

A.lirlrs, VA 22ZO2atO2,.t

. AgkNcY Ush oNLY (L-n

rc

Dank)

ir

Otth. ol MmI.moa

lz. tltfoHl

uAlE

October

id

Eude.(,

Pprwrt i.dElin
lJ. rcruxl

1993- |

PtC.sr p7oa.Ol22l,

IYr

Wd*ErtL

D'C. 20603.

ANU 9AIED suvEEu

fechnical/Current
ullUINS

Joint CB Technical Data Source Book,

Volume V, Blister, Blood, and Choking Agents.
Part 4, Agents HN, Q, T, L, and HL

NUMECFD

TECOM 8-CO-21 A-049-21 2

Contract DAAD09-87- D-0008

B. AUTHOR(SI

Parker, Don T.; Parker, Andrew C.

Properod by Aadrulie Rcscerch Coqroretioa, 660 South 20O Etst,

UT t4111-3t35
for
U.S. Army Dugrvry Proving Ground, ATTN:STEDP-JCP
Salt I-rke City,

Dugwey, UT 84022-5000
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AGENCY REPORT NUMBER

1. SUPPLEMENTARY NOTES

Project Manager for DPG is Kenneth S.K. Chinn

2..

DIsTRIBUTION/AVAILAEILITY

2b. DISTFIBUTION CODE

STATEMENT

Distribution limited to U.s. Government agencies only (october 19931. Other

requests for this document must be relerred to: Commander, U.S. Army Dugway
Proving Ground, ATTN: STEDP-JCP, UT 84022-5000

The chemical warfare agents discussed in this book were developed prior to World War ll,
none
have been used in warfare by or against U.S. military forces. Because materials of
but
greater toxicity have been developed, thess agents have bssn considered obsolete. Defense
capability remains a possible requirement because of the ease with which some of these agents
can be produced and the low cost of production. These chemical warfare agents, if used at
deliverable rates in the field, would cause casualties with days to weeks of incapacitation, but
few deaths would result from such uss. All are capable of causing skin blisters, eye injuries
and, at high exposure levels, various physiological responses such as respiratory and intestinal
iniury.
5. NUMEEF OF

I4. SUBJECT TERMS

Chemical defease, Chemicel wrrfare, Ageot HN, Agent Q, Agent T, Agent L,

Aosrt III- Aocnt IfT Nittnoen mrrstrrd, Iqvisitc- Scsouimusterd. Orvocn musterd.
Vesicetion, Cerciaogeoicity, Mechlorethamine, Physicd protrction, Protoctive
Deconteminstioa, Chemicd ageot destructioo.
tl. !E{;unll r cllltllrl(ialtun
/. "1srhing,
I'. SEUIJhI I Y UUDJFruA IIU
SEUUiiI I Y ULADJIIIUA IIt,N
OF REFORT

UNCLASSIFIED

OF TH]S PAGE

UNCLASSIFlED

54

PAGES

{crcluding Distribution)

16. PflICE CODE

20. LIMITATION OF ABSTRACT

OF ABTTRACT

UNCLASSIFlED
PrEib.a
2a&ro2

by

Arig srd.

23e.18

DOCUMENT UNCLASSIFIED UPON REPRODUCTION JCP-|, DPG

FORSWORI)
The Joint Chemicd/Biological (CB) Technical Data Source Book is organized as a series
of volumes, each addressing an identifiable area of information related to the andysis of CB
weaponri and defensive systems. Areas inelude chemical/biological agents, general models
weapons systems, chemical simulants, biological nonpathogens, and knowledge deficiencies.

This doorment, Volume V, Part 4 of the loint CB Technical Data Source Book is a
of blister agenti other than H, which was published as Volume V, Part 1. This
Source Book volume was prepared by Andrulis Research Corporation under contract No.
DAAD09-t7-D-000E. The au&ors would like to thank Kenneth S.K. Chinn for his
comprehensive review of ttris document.

discussion-

DOCUMENT UTVCLASS IFIED UPON REPRODUCTION JCP-|, DPG

TABLE OF CONTENTS

FOREWORD
LIST OF TABLES AI{D FIGURES

...

1. INTRODUCTION

2. NITROOEN

2.1

MUSTARDS

CHEMICAL COMPOSIIION AND PTIYSICAL PROPERTIES OF NITROGEN

MUSTARDS

3
3

2.3

CHEMICAL REACTIONS OF MTROGEN MUSTARDS

PREPARATION OF NrIT.OGEN MUSTARD

2,4

SYMPTOMATOLOGY

2.2

AI{D PATIIOI.OGY OF MTROGEN

MUSTARD

POISONINO
2.5
2.6
2.7
2.8

3.

MUSTARDS
TOXICITYOFNIIROGENMUSTARDS....
TIIERAPYANDPROPHYLNilS....
EMPLOYMENT ..
MECTIAMSM OF ACTION OF MIROGEN

.,....
.....,

SULFURMUSTARDS,TA}iIDA...
3.I CTIEMICAL COMPOSITION AND PHYSICAL PROPERTIES OF T AND Q
3.2 CHEMICAL REAETIONS
3.3 PREPARATION OF T AND Q
3.4 SYMPTOMATOLOGY, PATHOLOGY, AND MECHANISM OF ACTION
PRODUCEDBYTANDA ...
3.5 TOXTCTTY OFT AI{D a . . .
3,6 TIIERAPY AND PROPHYI.AXIS . .
3.7 EMPLOYMENT . .
......
LEWISITE(L)AT.TDMUSTARD/LEWISTE6L)
4.I CIIEMICAL COMPOSIIION A}iID PI{YSICAL PROPERTIES
4.2 CTIEIUICAL REACTIONS OF LE\I'ISITE
4.3 PREPARATION OF AGEITIT
4.4 SYMPTOMATOLOGY, PATHOLOGY, AND MECHANISM OF ACTION . . . .
4.5 TOXTCITY
4.6 PROPHYI-AXIS A!.ID TIIERAPY
4.7 EMPI,OYMEM ..
CIIEMICAL AGEITI'TS
5.1 DE]ECTION
5.2 PT{YSICAL PROTECTION
5.3 DECONTAIUINATION

5. DEFENSE AGAINST

6.

CONSIDERATION OF DISPOSAL PROCEDURES

ul

I7

2I
2I
2L

2I
25

25
27
27
29

29
29
32
13
36

3t
39
4T

4I

,,.,..

DEMILITARIZATION OF CHEMICAL AGEMS A}.ID MUMTIONS . .

6.1 INTRODUCTION ..

6.2

L4
18

4.

TI

...

42

47
47
47

DOCUMENT UNCTASS I FIED UPON REPRODUCTION JCP.L DPG

LIST OF TABLES AND FIGURES

Page

Table

l.
2.
3.
4.

Ch-emical Structure and Properties of HN

Physical Propenies of HN
Eruyme Inactivation by Vesicants in Wtro
Penetration of Human Forearrn Skin by Saturated Vesicant Vapor

t2

l4
15

i.

li**Ifi *#fffiffifi;i,,

9. Toxicity of HN-l

....... .

......

l5
l5

......

and HN-2 Vapor for Man

16

'
10. Toxicity of HN-3 for Man
11. Estimated Dosages for Nitrogen Mustard and H to Produce Skin Damage

l6
16

on Human Forearm

12. Cutanous Injury in Masked Volunteers Exposed to HN-l and HN-3 Vapor
while Wearing Nonprotective Clothing
13. Chemicel Structure and Properties of T and Q
14. Physical Properties ofT and Q
15. Lethal Dosage of H, T, and Q for Various Animds
16. Effect of Chamber Airflow Rate on Lettrd Dosage for Vesicant Agents
to which Mice Are Exposed
17. RElative Vesication Resulting from H, T, or Q Deposited on Human Skin .
18. Chemical Structure and Properties of L and HL
19. Physical Properties of L end HL.
20. Sequentid Effect of One Drop of Liquid Lewisite or Sulfur Mustard on
the Skin of the Human Forearm
21. Toxicity of L for Animds when the Entire Body Is Exposed to Agent Vapor . . .
22. Toxicity of L for Animals when Exposed to Vapor
23. Toxicity to Animds of Percutenoous Application of Liquid L . . .
24. Toxicity of Lewisite for Man

L7

22
23
26
26

26
30
31

34
.

36
37
37
37

Flgure

l.

Transformations of Methyl-bis-(p-Chloroethyl)-amine

lv

(IIN-2) in Water

DOCU M E N7 UNCLASS I F I ED UPO

N REPRO D UCT I O N JC P. I, DPG

SECTION

1. INIRODUCTION

Chemical compounds that have been included or considered for inclusion in the U.S. arsenal of
chemical warfare (CW) blister agents are the sulfur mustards, the nitrogen mustards, the arsenicals, and
certain mixures of these agents. The sulfur mustards GI, HD, and THD), composed of the active
ingredient bis@-c.hloroethyl) sulfide, were presented in the lolnt QumicalBblogical Technical Data
Source Bo,ot (SB), Volume V, Part I @ef. t). This document, Volume V, Part 4 of the Sowce Book,
contains infonnation on other blister-qpe CW agents. Section 2 addresses thenirogen mustards; Section
3, sulphur mustards T and Q; and Section 4, arsenicals Lewisite and Lewisite/mustard mixture. Section
5 addresses defense againstthese CW agents, and Section 6 discusses agent disposal.

The CW agents discussed in this doctment were, for the most part, developed prior to the end
of World War II, though experimental evaluation of some continued for several years thereafter. These
agents were selected as the most appropriate for use as CW agents from among a large number of
compounds that were oraluated. There is no indication that any of the CW agents discussed wore ever
used in military conflict.
With ttre development of nerve agents, which are much more toxic ttran ury of the vesicurt agents,
interest in further development of vesicants declined. However, recent employment of sulfur mustard
(H or HD) by Iraq and Iran has renewed interest in vesicants, particularly interest in defense requirements
should these CW agents be used against U.S. forces in a limited conflict.

DOCUMENT UNCLASSIFIED UPON REPRODUCTION JCP-|, DPG

SEETION

2.

NITROGEN MUSTABDS

2.1

CHEMICAL COMPOSMON AND PHYSICAL PROPERTIES OF NITROGEN

MUSTARDS

2.1.1

Introduction

In

lgii and 1935, lVard @ef. 2) studied the propertix

of chlorinated-*tryl amines including the

tertiary amines, which he found to have vesicant properties. Further study establistred the applicability
of these agents to military use. The designation 'mustard agent" has been given to these chlorinated ethyl
amines because of their struchral relationship and similarity in physiological effects to sulfur mustard.
In U.S. CW literature, nitrogen mustards are given the general symbol HN. Three of the tertiary
chlorinated *tryl amines were selected as CW agents and have been designated by the symbols HN-l,
HN-2, and HN-3. Designations by which these agents may be identified in various literature sources are

HN-l:

ettryl S, NH-LOST, NOR, nitrogen mustard-I, and NSC 10873;

HN-2: dichloren, N-Methyl-LOST, mustine, nitrogen mustard.2, NSC 762,

S,

and

l.

The

mechloroethamine;

HN-3: nitrogen mustard-3, TO.

2.1.2

Chemical and Physicd Propertix

The chemicd struc$re and properties of HN-l, HN-2 and HN-3 are listed
physical properties of these agents are given in Table 2.

2.2

CHEMICAL REACTIONS OF NITROGEN MUSTARDS

2.2.1

Reactions in Storage

in Table

The nitrogen mustards dimerize in storage as a result of self-dkylation. Dimerization is relatively

independent of the presence of metals such as steel, brass, or solder. The HN-3 is the most stable of the
three nitrogen mustards, HN-l the least stable. If HN-3 i. dry, it will store for a very long time witltout
excessive dimerization. Dimerization increases with the increase of storage temperature, and is relatively
rapid in 0re presence of polar solvents. Early evidence of the instability of HN-2 in storage eliminated

it ftom further serious consideration as a CVf

agent.

Dimerization of HN-3 yields, as a first product, an N.N.N'.N'-terakis- (2-chloroethyl)-piperamnium dichloride. Other products result from storage in the presence of solvents or acids (Ref. 4).

D O C UM E N

Table

l.

7 UNCrA SS t F t E D U p O N R E p R O D u c T t Oy,J_q ?:1_!

Chemicd Structure and Properties of HN.

HN-3

Chenricel Neme
Bie{2-chlorocthyl)

o6yluinc

Ethylbis(2-chlorocthyl)

(Rcf.

mcthylaoiac

Bie-2(chlorocthyl)

(Rcf. 3)

(Rcf. 3)

3)

rnine

Ethyltie{p.oNoroc6yl)

mino

@cf. 3)

2,2'dic.hloro-N-rethyl
rmino (Rcf. 3)

diethyl-

N,N-bis(2-chlorocthyl)

ncthyl-

Cblonmino (Rcf.

Tri(2+hlorocthyleminc

(Rd.3)

rmina (Rcf. 3)

Gef a.)

Tri{2+hlorocthyl) rmine

3)

2,2',2'-trichloto-tricthyl
rmino (Rcf. 3, 5)
Tris(p.chlotoethyl) enino
@cf. a)

Morhyl-bis (p<hloroerhyl)
enine (Rcf. 4)
Mechlorethenine (Ref. 6)
Chenrical Stnrcture

cH2cH2c,

cIt2clt2c,

oror*t

t--l

HrC{

ll
cH2cll2cr

clllrCHzCl

cllzc[2eg
ClCH2CIl2-ll.
cII2cH2c,

Chqnical Formule

cJ{,rc?rN

C,IIrCf2I.I

cfl,2crrI{

156.07

20,.54

Moleuler lfleiqht
170.08

Rete of HvdrolYsis

Vcry slow

Slow except in elksline

wetcr

Slow exccpt in dkaline weter

Pnoducts of Hvdrolysis

Hydroxyl

dcrivetivcs

Hydrochloric rcid

Dimerizetion
Complex

condensete

Triethrn6ll6ia6
Direrizetion

co2,Hcr,cr} Hro' N,
(estimated) (Rof. 5)

Odor
Fishy or muty

Soft soap to fruity

Nonc whcn purr

DOCUMENT U'VCLASS'FIED'JPON REPROOUCTION JCP.I, OPG

Table

2.

Physical Properties of HN..

HN-I

HN-2

HN.3

Liquid

oily Liquid

1.15 et 20"C

1.24 art25oC

Phvsicel Stetc et Room Ternperaturd

Uquid
Dercitv

&iquid ft/mf)
1.09 et 25oC

Dcnsitv (Veoor - es Conoamd to Air)

-.

5.9

5.4

._

?.r

Boilins Point

(cdculetod)
at
stmofphcnc pressurE
194cC

Dccomposcs bclow boiliag

75cC et 15 mm Hg.

Dccomposes below boiliry et

ilmotphefic prcssulla

2566C (crlculstGd)

Po"orp"Cgs bclow boiling at

ttEotphcnc prcssurc

Dccom oosition TclrrDcraturc

150'C (Rcf. 5)
Freczinq Tenrperature
-34cC

{O to {5oC

Hish

High

-3.7"C
-4"C (rclting) (Ref. 5)

Ilash Foint
High

Viscositv
5.9 cSt

rt 25"C (Rcf.

5)

Latnt Heat of Vanorizstion

77 cdlg

74 ctllg

78.8 cal/g

VaDor kessure (mm Hg)

0.24 rrt25oC

0.29 at 20oC
1.25 et 40oC

0.0109 rt 25oC

0.0110 et 25"C (Rcf. s)

et OoC @cf. 7)
0.0Cr26 et 10oC (Rcf. 7)
0.0069 et 20cC (Rcf. 1)

0.0009

0.0106
0.0164

rt 25'C @cf. 't)

rt 30"C (Rcf. 7)

Solubilitl in Weter
lZ

Sparingly

glt rt 2'C @ef. 7)

0.00E g/100g (Ref. 5)

O.5 gll et 20oC (Rcf. 7)

Solubilitv in Solvenb
Freoly solublo in ecolone rnd
othcr organic rolvcnts

Volebilitv

Soluble in acstouo and other

orgrnic solvcnts

Solublc in moct orgeaic oolvcnis:

cthers, bcnzcoc, rcclong, nrlfur
Euslrrd, e.hloropicrin (Rcf. 5)

(ng/n)

127

tt -lOoC

rt OcC
1,52$.t 2OoC
3,1O0 rt 30"C
308

'Drtr rcfcrred to ero

l-rom

3,5E0 rt 25oC
5,100 rt 30oC
10,q)O rt 40oC

RcllIunfess othffise dcslgnsted.

13

et

OoC

l?l.t?5"C

ItO * 300c
390.t 40oC
120 rt 25oC (Ref. 5)

DOCUMENT UIVCLASSIFIED UPON REPRODUCTION JCP-|, DPG

2.2.2

Hydrolysis

The nitrogen mustards ue slightly soluble in water and are very slowly hydrolped; HN-3 is the
least soluble. However, in water adjusted to pH t with bicarbonate, HN-l and HN-2 are rapidly soluble,
HN-3 somewhat less so. The hydrolysis products of HN-2 are shown in Figrre I (Ref. 4). The imonium
form and ehtorohydrin are soluble in water and are toxic. Only the product of the final stage of
hydrolysis, metryldiehanolamine, is nontoxic.

MI-2

cH2ol2cl

ll
,ll
r.mcrhyr.t{p<hrorocrhyr)

cthylcnirnoniumbn

cll

cH,N/
---r--_-

- *t'cxp'
-l

\-

Itf
r,
chtorohydrin. nrcthyt.p<hlorocrhyl- &rn-

phv&oxvc'lhvreminc

cH2cH2cl
A,?

cH3

cf{l
}\II2cH2oH

,ffi"'on'*

-'::

l.mcthyt-r{phydroxycrhyl) *riagfi
cthylcnimoniumbn
I ' : 'or/

i",

+N,ctI2CII2cl

Ar?
cry,clzor
^'?

T,
l-- T,
o(

II

g"ria-h,
"
I
|

+Ncl2crr2ct

{-*;",-"
-l*
-

glr,

-l l+/'c*zebor
cH3Y
I+
'
-'l-ctt2cH2oH
lornol2cH2ox

mcrhyrdicrlranotarnine

-\
cH2or2oH
-l

gIIz
I

CH.

l"

cI{3NcH2cHpH

Flgurc

l.

Transformations of Methyl-bis-(p-Chloroethyt)-emine (IIN-2) in V[ater

Concentrations of the end products of HN-2 hydrolysis have been shown to vary, depending on
the initial concentration of HN-2. lVith a low initial concentration of HN-2, the end product,
mahyldiahutolamine, prodominates; whereas, with higher initid HN-2 concentrations, thepiperazonium

DOCUMENT UruCLASS IFIED IJPON REPRODUCTION JCP-|, DPG

derivatives will predominate as the dimerization products. Hydrolysis of HN-l and HN-3 is closely allied
to ttrat shown for HN-2. However, HN-l is less susceptible to dimerization; HN-3 yields three imonium
ions as compared to two with HN-l and HN-2 (Ref. 4).

In unbuffered water containing a small percenege of niEogen mustard, the nitrogen musBrd and
the hydrolys-is products can be found in solution concrrrently after 48 to 72 hours and presumably will
remain in such a state indefinitely. Water treated with t percent HN-2 and allowed to stand at room
temperature for 48 hours or longer had a neurotoxic effect on laboratory animals. The solubility and
toxicity of the hydrolysis products in water are conducive to the poisoning of food and water by thxe
CW agents.

2.2.3

-'

Reactions with Acids

The reaction of principal interest is that of HN-3 and hydrochloric acid to yield tris-(2-chloroethyl)-ammonium chloride, a stable, water soluble compound that has the same toxicity as HN-3 and can
be stored indefinitely. As stated in paragraph 2.2,2,this makes it an effective poison for food and water.
A yellow crystalline picrate is formed when HN-3 reacts with picric acid. This reaction is used to
quantitatively identify HN-3 in solutions. Reaction with picrylsulfonic acid yields a more precise
quantitative assessment of dilute solutions (Ref. a). The HN-3 reacts with a number of other mineral
acids to yield toxic sals.

2,.2.4 Oxidation

and Chlorination Reactions

The nitrogen mustards are not readily oxidized, and only powerful oxidizers are effective in
oxidizing these agens. Potassium pennanganate, dissolved in dilute hydrochloric acid, slowly oxidizes
HN-3. Fuming nitric acid and chromosulfuric acid quickly react with HN-3 to form a number of
unidentified oxidation products. At elevated temperaturss the oxide of HN-3 is obtained through
oxidation by hydrogen peroxide (Ref. 7).
Chloride of lime and the chloramide.s commonly used as decontaminants for sulfur mustards either
do not oxidize or ineffectively oxidize the nitrogen mustards. However, several chloramides do react
effectively with nitrogen mustards, as does calcium hypochlorite. An excess of the reacting chlorine
compound is required to completely inactivate nitrogen mustard agents.

2.2.5

Reaction of the Nitrogen Mustards and Functional Groups

The nitrogen mustards react with a great number of chemical functional groups. However, the
reaction appears not to occur until thp tertiary amine has been transformed to the cyclic imonium form,
as occurs in the process of hydrolysis. The nitrogen mustards react with the amino group of almost all
amino acids and with organophosphate and sulftrydryl groups. They dso react with inorganic phosphates,
sulfides, polysulfides, and bisulfides (Ref. 7). Reactions occur more effectively at an alkaline pH.
The mustard agents inactivate or paftially inactivate a number of enzymu. The chloroethyl group
is the active alkylating component of both the sulfur and nitrogen mustard molecules. Consequently, the
action of nitrogen mustard should be expected to be similar to that of sulfur mustard. A degree of
similarity is demonstrated in the effect on enjzymes, as shown in Table 3.

DOCUMENT UruCLASSIFIED UPON REPRODUCTION JCP.L DPG

Table

3.

Enzyme Inactivation by Vesicans

iz Yirro.

.ffiffiffiiA-

Etzyr.

AA

Adcoylic rcid dsrminrro

2t40

Adcoylpymphoqhrtrro
Adcoylpyrophoephrtrsc (myosin)
Acrobic phoaphorylrse
Alcofol dchydr4coreo
d-Amino rcid oxidrso
Bctriac ddohl& oxidesc

2t{o

l)

up to
up to Z)

Crboryhsc

0
up to 20
0

Crtbcpsitr

Cholincstcnsc (scrum)
Cholincdcnsc Gnin)
Cbolinsstcnso (hdncy)

Cholinatcmr (cyc)

el-lod

Choliac oxi&gc

Chymprprin

2t{o
2t{o
up !o 20

zr{o

up to 20

91-r00
up to 20

9l-100
up !o 20

2r{o

2t40

61-90
up !o 20
up to 20
91-100

91-100

91-100

up !o 20
up to 2O

Chymtrypin
Crcrtino pborpbokinasc

Cytochrom oxi&ec
Dcutcrohcxokiorss
Glucoec dchydrqcorsc

91-100
0

61-90
0

2140

2t-60

up to 20

2140

Glutrmic rcid oridesc

2140

Glyccrolphoryho,kinrsc
alycorophoapbetc dchydrogcnrso

Glyordrsc
Hsxokinrsc
Histrninaso
Loucinc dc.Einrso

0
0

::

9l-100

2140

61-90

Mdic rcid dchydrogcoesc

21{0

Prprin

up to 90

PGpsi!
Pcpsimsc (swinc kidncy)

2140

ztio

;
up !o 20
up to 20

up to 20

.rt1:

up to 20

2t40

Pcpsiaogen

Popti&sc (conrm, plrsmr, skin, lung)

Phcayldrninc dcroineso
Phospbrtrrc (rid rnd dkrlirc)
Pbospborylrsc
Pyrophospbrtrso
Pyruvrtc phoryho&inasc

Pyrwic oridrc
Srccinodchydrogmrsc
Srcrrsc

91-100

91-100

2140

up to 20
ttp to 20
up to 20

61-90

6r-90

2140

21.60

6140
2t-60

up to 20

21{o
u, a r?,
61-90

2140

up to 20

Ttymnrrclcodcpolymnse

Trioccphocphrto dchydrogmese

2t40

Tryprin

2140

::

2140

Uricrsc
VdiDe dcrnirrsc
'D& (!-Ctrlorcatryl) rulfrdc
rMahyl-Dir (P+hbroc*hyl) rminc

up to 20

up !o 20

'rris (F-Chlorocthyl) rminc

ho

dete

NOTE: Studrrd brrtmcnt L conridcrcd to bc incubrtion with 3 millirnolcr of H or cqually rctivc rmounr of othcr
n9rtcnt for onc.halfto ons hour,

DOCUMENT UA'CLASSIFIED UPON REPRODUCTION JCP.I, DPG

2.3

PREPARATTON OF NITROGEN MUSTARD

Ward (Ref. 2) reported pr@aration of the primary and secondary chloroahyl aglines (preparation
of both had been previously reported) and the tertiary chloro*hyl amines (preparation had not been
previously reportd). He reported the tertiary chloroahyl amines to have caused edema followed by
blisters on his hands, which required many weeks to fully heal. Tho primary and secondary chloroethyl
amines are not vesicants. IIe prepared ttre chloro*hyl amines by the reaction of thionylchloride in
chloroform on the corresponding ethanolamine.
Essentially the same procedure was used for plant production
compound of choice as a CIV agent. For HN-3, the reaction is:

of HN, partioilarly HN-3, the

N(CfiI2CII,OiO. + 3S0C|,'JV(CII2CIILC}T' HCI + 350, + 2IICI

fire chloroethylamine occurs in the reaction

as a hydroctrloride sdt, which is converted to the free base

by aqueous sodium hydroxide. Ettranolanine is prepared by conversion of *hylene oxide with ammonia
by excess hydrogen chloride. Other procedures have been prolnsed @ef. 4). The indusnial IIN-3 is
ordinarily a dark brown color and will contain 95 to 97 percent tris-(2-chloroethyllamine (Ref. 7).

2.4

SYMPTOMATOLOGY AND PATHOLOGY OF NTTROGEN MUSTARD POISONING

The nitrogen mustards are vesicants urd produce erythema of the skin, followed by development
of skin lesions. The skin rash is violet in color (Ref. 7). The comparative vesicurcy of ttre three
nitrogen mustards and H are H > HN-3 > HN-2
HN-l. This order of vesicancy and lesion
production applies both to vapor and liquid exposure @ef. 4). The lesions caused by HN are reported
to be less deep and to heal more readily than those causod by H, but they are more painful. A rash may
appear within an hour following exposure to a high concentration of agent, but with exposure to what

>

may be mnsidued a field concentation the rash may not appear for 6

8 hours. Large lesions

indicative of exposure to a subsuntial concenuation are accompanied by a deterioration in health and loss
of weight.

The upper and lower respiratory tracts are affected by respiratory exposure to HN vCIor or
aerosol. Mild intoxication causes catarrh in the larynx and other air passages. More severe exposure
can damage lung tissue, and the pulse and respiratory rate may increase. Muscle sparnu may accompany

injury to the central newous system, and the gastrointestind tract may be damaged (Ref.

injuries in individuals exposed in chamber trials to low dosages of

HN-l

7).

No systemic

and HN-3 have been manifesr

(Ref. 4).

The characteristics of niEogen mustard intoxication in animals, for each of the three niuogen
mustards, ue briefly presented in the following puagraphs.

DOCUMENT UNCTASSIFIED UPON REPRODUCTION JCP.I, OPG

2.4.L

Symptomaology and Pathology Produced by

HN-l in Animals

Intravenous or subcutaneous injection of HN-l in mice caused netrvous system disturbances

raoging from poor coordinationto tremors and conwlsions. In rabbits, intravenous iujection first caused
centrd neryous system stimulation followed by dqression urd rapid death. Anorexia, emaciation,
lancopenia, aod diarrtea occurred with applicuion of HN-!, to the skin of rabbits. Dogs receiving
cuuncous ctrdlenges showed symptoms of shock. Ras given inravenous injection of HN-l showed no
early overt symplosa, but nzurological injury was wident after 3 or 4 days, followed by death. Internal
manifestations.in rats receiving an LD, dose of HN-l by four routes-of invasion (intravenous,
subcutanous, cutaneDus, and vapor exposure) were mild to moddate in regards o total systemic injury,
lymphoid atrophy, myeloid injury, leucopenia, and enteritis. With intravenous and cuUneous sf,posure,
weight loss was severe (Ref. 4). Observed effects were not deemod respottsible for the deaths of the
animals.

7.4.2

Symptomatology and Pathology Produccd by HN-2 in Animals

When HN-2 was administered to laboratory animds by parenterd i4jection, a cholinergic action
similar to Orat produced by acetylcholine was observed; however, inactivation of ctrolinesterase is
apparently not involved. The agent is responsible for a pardytic action in animals, affecting first the head
and neck and then the extremities and tho thorax. Cessation of respiration follows. Ras receiving HN-2

intravenous injertion demonstrated narologic injury, but cutaneous or subcutaneous

adminisuation of IIN-2 did not cause neurologic symptoms. In rats, a reaction related to the alarm
reastion was observed. In dogs, the agent frequently caused vomiting, diarrhea, intestinal bleeding,
reduction in or loss of control of body temperaEre, anorexia, dSilitation, and eventud respiratory
failure, perhaps associated with circulatory intribition. Direct injury to the heart has not been indicated.

vapor

or

Events associated with administration of an LD, dose of HN-2 consisted of a symptomatic latent
period of I to 2 days; however, during ttris time, adverse respome and injury to various internal organs
was occurring, followed by anorexia, weight loss, diarrhea, prostration, ard death. Animds that survived
effects. Observations on the effect of HN-2 on
the LDr, for the most paf,t, did recover from

dl

hematopoiesis indicates early leucocytosis, followed after a day or rwo by leucopenia. This effect has
been observed with agent H.

Sensitization to HN-2 has been shown to develop in the animal body as a result

of

repeated

exposure to smdl liquid doses of the agent. Also, tolerance has been demonstrated following repeated
exposure to a series of small doses of agent administered over several months.

2.4.3

Symptomatology urd Pa0rology Produced by HN-3 in Animals

High subcutanous doses of HN-3 result in conwlsive action in various animals. Death is
attributed to respiratory failure presumably associated with restricted respiratory exchanges.

WiOr doses below the immediate conrnrlsive level, a progressive development of muscular
weakness, diarrhea, mldness, hyperexcitability, and retropulsive movements and tremors culminated in
prostration and death from respiratory failure. The general pathological course is lymphoid atrophy, bone

10

DOCIJMENT UNCLASSIFIED UPON REPRODUCTION JCP.L DPG

manow deterioration, and failure in blood cell generation; thus leucopenia, enteritis, and weight loss were
observed. As with the other nitrogen muserds and with agent H, some variation, though less so with
agent H, was obsewed for the different routes of agent entry into the urimal body.

2.4.4

Sympomaology and Pathology Produced by HN in Man

Six human subjects, each at a termind stage of an incurable disease, responded to daily small
intravenous doses (0.1 mg/kg) of HN-3.HC| wittr nausea, vomiting, headache, malaise, drowsiness, and
marked reduction in blood cdls. In normd volurteers, a single dose of 0.1 mg/kg of HN-3'HCf caused
headactre and nausee 8ftr t hours. Dizziness and weakness dso occurred in some, and all volunteers
developed ttrrombophlebitis. No vomiting or anorexia occured.
Ingestion of 2 to 6 mg of HN-2.HC! in tap wuer resulted in anorexia, resurrent nausea and
vomiting, tenseness, gassiness, and mild diarrhea dong with depression. lngestion of I mg produced
very mild to zero symptoms and pathological murifestations. Severity increasod with inreased dosages.
Recovery was within 48 hours.
Inadvertent exposure !o HN-l and subsequent intoxisation in man caused laryngitis, bronchitis,
hoarseness, coughing, elevatod tmperafire, nsusea, and vomiting. Inadvertent exposure to minute
emounts of HN-l vapor caused conjunctivitis, asthrnafioid bronchitis, but m effect on temperature or
blood properties (Ref. 4). Two of six humans exposed acciden0y to HN-2 vapor complained of nausea
5 hours following exposure, and one vomited until 12 hours after exposure. Two showed a decline in
leucocyte count, but soon recovered (Ref. a). Persons accidently exposed to HN-3 vapor suffered eye
and upper respiratory tract irritation, headache, and vomiting (Ref. a).

2.4.5

Symptomatology and Pathology of HN Transformation Products

Each of the three nitrogen mustards hydrolyzes to yield hydrolytic products, particularly the
imoniums and chlorohydrins as shown in Figure l. These are readily formed in water and in other
aqueous-based solutions. They have been examined as to toxicity, symptomatology, and pathology. In
general, they are equal in toxicity to the basic nirogen mustard compound and, with slight vuiation,
elicit the same symptoms and pathology as the corresponding niuogen mustard Eef. a).

2.5

MECHANISM OF ACTION OF NITROGEN MUSTARDS

2.5.1

Physiological Action

The action of vesicants involves penetration of at least the upper skin surface. Peneuation of the
skin by the mustard agents has been suggested to be related to fieir solubilities in lipids, a property of
both the sulfur and nitrogen mustards, which facilitate penetmtion through oil secretions around hair
follicles. However, penetration of skin ueas devoid of pors or hair follicles has been demonstrated (Ref
4). The rates of penetration of HN-l, HN-3, and H are given in Table 4.

1l

DOCUM ENI UNCTASS IFIED UPON REPROD UCTION JCP.I, DPG

Table

4. Penetration of Human Forearm Skin by Saturated Vesicant Vapor in Exposure Cup (Ref. a).

Agcnt

Room
TGDPdrturE

HN.I

,
HN-3

(r)

Numbor of
Erperimmts

70:73

u4

60

E7

4t-49

49

7t-72

5GS2

t5-87

4749

72-73

t5

('F)

Pcoctrrtion

Rolrtivo

HuEidity

Voletilitf
(ne/f)
0.74

Rsto

fuglcm2/min)
1.4

2.7

t.$
l.t

56

3:3

5.1

45-48

t5

0.10

0.

474E

36

0.18

o.29

2.t
l8

'Cdcuhud on thc maraption rlut lha tor?cnurr of drc poeutioo eup ru thrt of tha mom.

The nitrogen mustards, like H, react immediately with animd tissue constituents, and their action
on the tissue is rapidly irreversible.
The view regarding the mechanism of action of niuogen mustard has evolved to the present from
the era of lYorld War l, when the furmation of hydrochloric acid by mustard vapor entering the body
was assumed to be responsible for toxicity. Little research was conducted between the hro world wars,
but during World War II extensive research demonstrated that alkylation of animal tissue constituents war
the action of the chloroatryl grcups of the mustsrd molecules. It was also observed that dkylation

required the transformation of the nitrogen

or sulfur molecule to the cyclic ettrylenimonium or

the

ethylenesulfonium cations of nitrogen or sulfur mustard, respectively. It was recognized that ttrese cations
produced a qpe of action on cells unlike any other chemical agent, but not unlike the action of radiation

Eef. t).
It has been proposed (Ref. 9) that sulfur mustard forms the cyclic imonium ion, which reacts with
and dkylates electron-rich molecular structures such as sulftydryl and amino groups. Upon entering the
skin, the irnonium ion dkylates the purine bases, quinine and adenine of deoxyribonucleic acid @NA),
forming apurinic sites. These are acted on by apurinic endonucleases, leading to removal of the dkylated
bases and breaks in the DNA. The DNA repair requirement actiyates poly(ADP-ribose) polymerase,
which rapidly depletes cellular nicotinamide adenine nucleotide (NAD). This depl*ion, which begins
within ur hour of exposure to the chloroahyl imonium ion and reaches a marimum in about 4 hours,
inttibits glycolysis and releases cell proteases, which results in cell necrosis (Ref. 9). CIher mechanisms
of the action of sulfur mustard on animal tissue have been postulated (Ref. 10), based on some
experimental support. Because the alkylating moiety of the nitrogen mustards is the same as in sulfur
mustard (i.e, the chloroahyl group), it may be expected that ttre nitrogen and sulfur mustards have the
same mechurism of action.

In some research, differences between the action of sulfur and nitrogen mustards have been
observed. It was repofied in 1952 that HN-2 reacted with adenine, quinine, thymine, and uracil ln vitro
(R,ef. I l). A subsequent report, which discussed the action of a npre monofunctional sulfur mustard on
Tl bacteriophage, indicated that the sulfur mustard reacted with quinine and adenine bases of the virus

t?

DOCU MENT UNCTASS IFIED UPON REPRODUCT ION JCP.I, DPG

DNA, whereas the niuogen mustard reacted only with the quinine base. The sulfur musurd inactivated
the vinrs, whereas the nitrogen mustard did not Eef. 12).
Depression

of glycolysis resulting from

of tissue to HN-2

has besn observed and

associated wi$ a depl*ion of nicotinamide adenine dinuclotide (Ref. 9). The connrlsant action of HN-2
may be ascribed to iB effect on acetylcholinesterase and other choline compounds, attributed to the
similuity of choline to the ethylene imonium compounds. This does not occur wittr the sulfur mustards,
presumably because of the instability of the ethylenesulfoniums of the sulfur mustards (Ref. 10). The
HN-2 has been shown to desrease membrane fluidity and membrane protein-activity.
exposure

Membrane proteins of human erythrocytes were preferentially alkylaed by HN-3, most

significantly, spectrin. The HN-3 reacted extensively with various hepaocpe membrane proteins.

2.5.2

Chernotheraputic Action
Because the physiological effect

of the mustards on tissue involved whole cells having relatively

high rates of grounh and multiplication, the possible adverse action of mumrd on cancer cells was
investigated. Tho action on cells was a result of the formation of the cyclic imonium ion. The
ethylenimonium ion of nitrogen mustard is less reactive and, thus, more stable than the short-lived
*hylenesulfonium ion of sulfur mustard. The hydroclloride salt of the cation can bo diluted in saline
to yield any desired concentration suitable for adminisuation. For this reason, the nitrogen mustards,
particularly HN-2, have been employed as therapeutic agents (Ref. 8).
The first Orerapantic work reported was with uansplanted lymphosarcoma in mice. The tumor
was quickly eliminated in response to a near-toxic dose of HN-2, but subsequently reappeared.

In medical literanre, HN-2 is sometimes refefred to as mechloroethaurine, or simply nitrogen

mustard. Nitrogen mustard has been most effectively employed in the treetment of Hodgkin's disease
and has been successfully used in treating various other forms of cancer (Ref. l3). It frequently reduces
the cancerous tumor by induced cell apoplosis followed by removal of the dead cells by phagocytosis
(Ref. 14). Although complete remission associated with early treatment has been reported for a number
of types of cancer (Ref. 13), the remission associated with HN-2 treatBrent is frequently of short
duration. The recurrent cancer may respond to subsequent treatment, but the cancer cells ultimately
become refractive.

Many mmpounds conaining the two chloro*hyl alkylating $oups essential to tbe effective
antitumor activity related to HN-2 have been formulatcd. The first clinically effective ctremtherapeutic
agent was HN-2 (Ref. l5), and HN-2 and its derivatives such as phenylamine mustard (melpholan),
cyclophosphamide, and chlorambucil remain among the rnost effective chemotherapeutic agents (Ref. 16).

2.5.3

Carcinogenicity urd CIher Actions

Aside ftom the uses of low doses of HN-2 in treating human cancer, extensive exposure of
to nitrogen mustard has not been reported, and a basis for evaluating the carcinogenicity of
nitrogen mustard is absent. The lesser reactivity of nitrogen mus&ud, as compared to sulfur mustard,
humans

13

DOCUMENT UNCTASSIFIED UPON REPRODUCTION JCP.I, DPG

may indicate a lower likelihood of a long-term effect. Invxtigations that have assessed the relationship
of cancer incidence to exposure to mustard, presumably sulfur musurd (Ref. l), indicate that short-term
exposure
relatively high concemations of sulfur mustard do not eppear to be responsible for an
increased incidence, at least not a suilisticaily significant increased incidence of cancer. In a population
of factory workers exposed to very low levels of sulfur mustard over a period of several yearc, a definite
link betryeen mustard exposure and various cancers, as well as other ailments, was indicated Eef. l).

An attempt was made in a rcccnt publication (Ref. 17) to litrk canc,er and serreral other ailmens
to exposure o possibly high, though sublethal, doses of mustard over a perid of a few days. The
assumptions made in that publication regarding carcinogenicity of mustard are questionable, Subsequent
to exposure to mustard, studied populations have had years of variod lifestyles, environmeotal exposures,
dias, and ocqrpstiorn as well as difrerent heteditary characteristics @ef.
These populations are
not easily amenable to ury definitive evduation that would support the conclusions of the referenced study

l0).

Eef. l7). A more realistic and supportable evaluation was prcsented in recoguizing that bronchitis
arising ftom prolonged exposure to mustard may predispose a person to have respiratory problems
including cancer of the respiratory system. However, an increase in the incidonce of cancer associated
with exposure to mustsrd at doseges to which populations have been exposed experimemally or in combat
has not been subst8ntiated as being statistically significant and must be viewed as negligible (Ref. l0).

2.6

TOXICITY OF MTROGEN MUSTARDS

For tho nitrogen mustards, most toxicity or dose response data for man and animds were obtained
during World War II, a period when an active search for effective CIV agents was pursued. All of the
data obtained were ftom laboraory work which was summarized in 1946 (Ref. 4). Values given in more
recent publications dmost always correspond to 0rose published in 1946. Howwer, rmre recent data for
HN-3 toxicity for laboratory animals have been included @ef. 5). The toxicity of the three nitrogen
mustards for laboratory animals is given in Tables 5 through E. Estimates of toxicity for man are in
Tables 9 through 12.

Table

5.

Toxicity of HN-l for Laboratory Animals (Ref. 4, 7).

Rouia of Intoxication

Animrl

Cutrnoous

Subcutrncou Intrrvenou

Iutreperiloncd

Orel

(Modira Lcthd Dosc, E8/kg)

Mousc

l3

R8t

t7

Rlbbit

l5

1.0

r.05

1.45

1.0

No &n.

t4

0.5

2.5

2.0

<3.0

DOCU MENT UNCTASS I F IED UPON REPRODUCTION JCP-|, DPG

6.

Table

Toxicity of HN-2 for Laboratory Animals (Ref. 4, 7)

Rouio of Intoxication
Cuteneous

Animal

Intrrvenous

Subcutraoous

Orsl

(Mcdim Lcthel Doae, mS/kS)

Mouso

29-35

2.64.0

2.0

10-20

Rrt

t+an

1.9-2.O

1.1

ro-85

Rsbbit

L2-t7

3.0

1.6

t2-17.5

Guince Pig

>E

Do8

Gort

20

< 1.0

<lm

<50

Mootcy
'No

t2

&tr.

Table

?.

Toxicity of HN-3 for Laboratory Animals (Ref. 4, 5)

Roule of Intoxicetion

Aaimel

Cutaaoous

Subcuteaous latrevenous

Intnpcritoneol

Oral

(Medien l.cthel Dose, mS/kg)

Mousc
R8t
REbbit

7-10

2.M.9

l-2

7.0

2-5

2.O

o.7

4.9

5-19

2.5

r9

10

_t

< 1.0

t0

20

2G30

Do8
Goet

Guiaer Pic

5-20

20

2G.30

'No detr.

Table

8.

Toxicity of HN-3 Vapor for Laboratory Animals (Ref. 5)

Aaimar

r,l{El5ll

Mousc

165{00

Ret

670-17fi

Guinee Pi3

l000-2300

Rsbbit

500.830

Clt

40G.1000

Do8

400-1500

Goet

500-1000

l5

DOCTJMENT UIVCLASS IFIED UPON REPRODUCTION JCP.I, DPG

Table

9.

Toxicity of

HN-l

and

IIN-2 Vapor for Man (Ref' 3' 5)

Route of Intoxicrtioo

L(Ctb (rng'urin/d)
HN.I

I{Ct)o (mg'min/m)

(ct)e

Pcrcutrnous

1,500

20,(no
9,000

2N

I(Ct), (mg'min/mt)

HN-2

Inhelation

,,:

-t

2,5q)-9,0O0

100

(mg'nin/m3)

'No detr.

Table 10.

Toxicity of HN-3 for Man (Ref. 3, 5)

*.uorroo"o ,r"
L(CQ5CF (mg'min/mr)

-a

LDse (mg&c)
I(C$str (mg'min/n)

200

**"rroo
,,:*

'3S*
1,500

10,000

0;
2,500

(meskd)
70 pg (to

42

E(Ct)sd (mg.min/m)
lc*hrl douge.
'Mcdirn
DMcdirn lcthrl dorc.
'Mcdirn incrpeciteting dongc.

Table 11.

ffi

'It{cdien
dete.

doragc

produce

or dorc to hitirl lymPtomr.

'No

Estimated Dosages for Nitrogen Mustard and

Damage on Human Forearm (Ref. a).

H to Produce Skin

Vapor Train

Agcot

Ervtheme

Blistcr

-CuP.

Tcst

VesicancY

(mg'min/m!)

<430

2,500

3,500

HN-I

2,7&

>21,000

18,(n0

HN.2

1,2@

5,800

HN.3

/100

1,800

TrIo dete.

16

3,7N

DOCU MENT UIVCLASS IFIED UPON REPRODUCTIO N JCP-|, DPG

Table 12.

Injury in Masked Volunteers Exposed to HN-l and HN-3

Vapof while Wearing Nonprotective Clothing
Cutaneous

Number

of

Sovcrity of

Vrpor

Injurf

Conccotration

Atoot Volunters (14.nin/6)

l0
l0
HN.I

10

100

1.3

1.2

0.3

2@

1.4

1.4

300
300

3.3

4.6
0.6

t.2
t.7

2.2

4.0

0.3
0.6
0.6

1.8

o.5

o.2

3.0
4.0
2.0

1.9

0.8

50
100
150
150

0.2

6
6

r50

1.5

4.0
0.0
0.3

?50

2.5

1.5

350

4.9

?.6

I
8
E

1.9
1.8

' Exporcd to HN-1 rnd HN-3 Vepor for @ minuta in

Humidity
t Scvcrity of Injury is: 0

No rcaction;

I:

3 = lntcorc crythcma; 4 =

2.7

of Body

450
760

HN.3

RGst

chambcr at

1.5

--

1.8

o.7
0.E
1.7

90'F rnd 65 Pcrccnt Rcletivc

Mild crythcma; 2 = Modcratc cr;nhcma;

Erythema with cdcma;

5 = Vcriclc

THERAPY AND PROPHYLAXIS

In general, therapy for intoxication by nitrogen mustard will be essentially the same as for sulfur
mustard intoxication. Protective measures, first aid, and therapy are described in U.S. Army Field
Manual 8-285 @ef. l8). The vesicant agent protective ointment M5, containing chloramide 5-330, is
applied for sulfur mustard exposure and should be used for eryrcsure in the field when identification of
the agent is not made immediately- However, chloramide 5-330 is relatively ineffective against the
nitrogen mustards.
First aid decontamination involves removal of evident droplas of liquid agent on skin or clothing
by lifting or blotting, followed by application of decontaminant pads urd powder. Treatment of skin
intoxication involves management of blistered areas. Blisters should be drained and areas protected
against infection. Infected areas may be treated wittr appropriate antibiotics. Dressings should be
changed every two to three days.

Liquid contamination in the eyes must be removed immediately, within seconds, by irrigating the
eyes with water from a canteen or other clean water supply. In a contaminated area, this should be done
while holding the breath between doffrng ard donning of the mask. Eye intoxication is treated with eye
ointments. Pain is alleviated witlr morphine or other systemic medication, AEopine drops may be
applied. A drop 0rree times daily witl aid in alleviating pain associated with swere photophobia and
blepharospasm. Sulfacgamide may be applied to control infection.
17

D O C U M E NT

U/VCLASS I F I E D U PO

N REP RO D U CT I O N J CP.I, DPG

espiraory involvement, in mild eases, is treated symptomatically o relieve cough and mild pain.
Antibiotic treatment is required if bron&opnaunonia dwelops. SubctUneous atropine injection may be
administered to relieve gastrointestinal distress caused by mustard intoxiceion. In sevcre gases, shock
therapy and administruion of electrolytes may be required. Atropine administration to allwiate the
conwlsions utd paralytic effects of nitogen mustard has been only slig[0y beneficid.
R

If exposure to mustard has been light, as widenced by mild symploms usually limited to
conjunctivitis and erythema, trestment may be limited to suppoftive serc. In such cias6, recovery will
be uneventful cnd complete in tsr,o to three weeks.
Experience witlt more severe cases of sulfur mustard intoxicuion has been obtained from
treatment of hospitdized Iran-Iraq war patients (Ref. 19, 20,21,22,23). In general, the treatment of
skin lesions was as for thermal burn victims; blisters were drained and moist occlusive bandages applied,

or the skin surface was left uncovered. Sulfadiazine and furacine were applied and, in swere cases,
cofticosteroid ointment was applied. Severe conjunctivitis was treatod with hydrocortisone ointment.
Extreme cases of @rnea injury were corrected by cornea fansplans. Systemic sy-trrptoms required
trestment with electrolyte therapy and parenteral fluids and blood ransfusion. Respiratory symptoms are
0te most life-threatening and have, in some cases, required tracheotomy. Therapetrtic bronchoscopy was
administered to clear air passages of some patients, and oxygen inhalation was required by some. There
is essentially no experience with treatment of cases of nitrogen mustard intoxication.
Some prophylactic research on the toxic effects

of HN-2 has been stimulated by its use in the

treatment of cancer. Early experimental work (Ref. 4) demonstrated the beneficial effects of
administering thiosulfate to animals coincident with exposure to nitrogen mustard. Later work (Ref. 2a)
showed a suppression of the oxic action of HN-2 and indicated ttrat Ore suppression was accomplished
by degradation of the HN-2 in the extracellular spase. Precursors of thiosulf*0, which promotes
generationof thiosulfate within animal cells, were administered to animals exposed to HN-2. Suppression
of the toxie effect of HN-2 wes not as great with these precursors as with sodium thiosulfate. The
adminisration of seroonin and histamine antagoniss (Ref. 6, ?s}suppressed the oxic effect of IIN-2
in mice. The HN-2 was administered to mice as a single inuaperitoneal dose of 5 mg/kg, which was
lethal to greater than 85 percent of the nonantagonist-treated controls. Antihistamine administered
intraperitoneally 4 hours prior o HN-2 injection, and 4, E and 24 hours following HN-2 injection had
a pronounced effect on survival rate of mice. olre antihistamine preparation was slightty effective in
increasing survival rate when administered 48 hours following injection of HN-2. The serotonin and
histamine anugonists did not interfere with the suppressive effect of HN-2 on canoer growth in mice.
other compaitive scavengers of nitrogen mustard, in addition to thiosulfate and
are cysteine, glutathione, and cystamine and its derivatives (Ref. 10).

2.8

is

derivatives,

EMPLOYMENT

The nitrogen mustards were developed as replacements for H under specific conditions. Because
IIN-2 is unstable, it is no longer considered to be a suitable CIV agent. However, its use in the treatment
of some types of culcer has resulted in continued investigation of its properties.

r8

DOC U M E N7 U'VCLASS I F I E D U PO N

EP RO D U CT I O N JCP. I, DPG

During World War II, the Germans socked HN-3 as the chemicd component of high explosive
dremical artillery shells. Based on research during World \[ar II, both HN-3 and HN-l were viewed
as useful CW agents. These agenrc freeze at a much lower temperature &an H. Agent HN-l is more
volatile, while HN-3 is much less volatile than H. Agent HN-3 can be slored indefinitely without
appreciable loss of effectiveness, it is stable when disseminated by high explosive munitions, and is a
potcntial barrier agent. Of the vesicant mustard agents, HN-3 is the rnost toxic.
In field trids conducted to investigate the effectiveness of HN-l and HN-3, af,ea coverage dosage
Ievels attained.were somewhat less than those for agent H. Early tests indicated that the chloramideimpregnated U.S. &emical clothing, presumably impregnated with the chloramide 5-330, did not protect
tr@ps from the vapor of these CIY agents. These findings enhanced the expectation of their value as CW
agents. Subsequent testing showed that trro layers of clothing impreguated with another chloramide
designatcd CC-2 did protect against HN-3 but not HN-I. Charcod-impregnatod clothing did provide
protection against boft nitrogen mustards. Agent IIN-I is rolatively ineffective as a vesicant, and was
superceded by other materials.

In 1946,

as a result

of field trials and known proprties of HN-3, an effective use was proposed

(Ref, 4):

"It is believed that in high explosive bombardments an occasional high explosive chemical
shell charged with HN-3 and indistinguishable upon detonation from ordinary highexplosive would have been used. HN-3 possesses &e stability to withstand destnrction
during the explosion of the shell and the lack of odor to escape ready detection except by
chemical methods. It is believed that the potential harassing and casualty-producing
effects of the vapor slowly evolved from the contaminated terrain might exceod those of
the initid cloud. The duration of danger from the vapor, the time inte,rvals required for
the ovolution of casualty-producing dosages, and the areas over which effests would be
produced would depend on meteorologicd conditions. As an example of the order of
magnitude of the hazafi
- in warm weather, explosion of a single M47A2 bomb
(containing 67 pounds of HN3) resulted within 4 hours in the attaining of a dosago of 100
mg'min/m3 of vapor over approximately one-half of an artillery square, and of
250 mg'min/mt over about one-fuurth of an artillery square. A dosage of 250 mg.min/m3
should more than suffrce to produce totd disability of severd days' duration due to eye
injuries, and possibly severe respiraory injury as well.'
With 0re development of the more oxic and persistent agent VX, the military vdue of HN-3 was
overshadowed. But the favorable properties of HN-3, as stated above, and the ease of its preparation may
still make HN-3 a CW agent useful to a nation seeking an unsophisticatod CW capability.

l9

DOC U M E N7 UIVCLASS I F I ED U PO N R EPRO D U CT IO N J C P. I, DPG

SECTION

3. STJLFUN,

MUSTARDS. T AND O

3.1

CHEMTCAL COMPOSmON AND PHYSTCAL PROPERTIES OF T AND Q

3.1.1

lntroduction

The sulfur mustard compound designated as Q was described in 1921 afr 1922 (Ref. 26) as
by the action of thionylchloride on the hydroxy compound corresponding to 1,2 bis-(Bchloroethylthio)ahane (Q). In 1931, it was reported (Ref. 27) that the incompl*e chlorination of
thiodiglycol, induced by modification of the thiodiglycol process for the preparation of H, resulted in the
production of a mixnre of H and T along with a smdl anount of Q and some impurities. Interest in T
and Q was a consequence ofthe fact that ttreir toxicities are higher and their persistencies are greater than
synthesized

those of H.

Agent

T may be designated oxygen mustard.

Agent Q is referred to as sesquimustard or

sesquiyperite.

3.1.2

Chemicd and Physical Properties

The chemical structur and properties of T and Q are listed in Table 13. The physical properties

of these agents are given in Table 14.

3.2

CHEMICAL REACTIONS

Agent Q is a solid at most atmospheric temperatures. If disseminated by high explosive shell, the
of the explosion results in the decomposition of some of the Q, and the principal decomposition
product is H, some of which will appear as a vapor in the resultant toxic cloud. If flashing occurs on
dissemination of Q, the principal decomposition product will be hydrogen chloride (Ref. 30).
heat

Agent T reacts with various chemicals somewhat similarly to H; however, unlike

H it

does not

react with alkyl iodides, chloramine-T, mercuric chloride or iodide, iodine, or bromine, it is not oxidized

by hydrogen chloride at l(X)"C, but at higher temperatures is decomposed to H and water @ef. 31).

3.3

PREPARATTON OF T AND Q

3.3.1

Preparation of

Agent T, or oxygen mustard, was fust prepared as a result of partial ctrlorination in the
thiodiglycol method of preparuion of H. This modification was carried out by preheating the thiodiglycol
to 60oC, then mixing it with conoentreted hydrochloric acid, during which, over the period of an hour,
the temperature rises to 110 to
Variations in conditions, principally temperaturs, varies the
proportion of H produced. The normal product ratio is 60 percent H and 40 pereent T (Ref. a).

lls'C.

2l

DoctJMENruNct:Asslr_EpuPgtyE!,-!tc,P!9r!o-ry_!ct-!,.?r9

Table 13. Chemical Structure and Properties of T and Q.

a
Chenricel Nrme

Bist42{hlotgthylthio)cthy[ othcr (R.f. 3,

1,2-Bis{hloroG6ylthio)+thuc (Rof. 7)
1,2-Bir(p-c.hlorocthylfio)c6re (Rcf. 4)
I :2-Di{2+hloroothylthio)cthrnc @cf. 28)
Ethyleoc bir p-chlorocthyl nrlphidc (Rcf. 26)

2-2'Bi{2-chlorocthylthio)dio6yl othcr (Rtf. 7)

Bidf -chlorccthylthioothyl)cthcr (Rof. 4)
2:2' -Di\24loroertylthio)dierhyl othor (Rcf. 7)
Ctrcmicd

Stnrtrre

Chemical Formuh

qH'PrPs,

c#r2s2cr2

Moleculer Weiqht
%3.3 (Rcf. 3)
263.2 (R:et.29)

219.2 (Ref. 7)

Hvdrolysis
Hydrolyscs rolrtively slow (Ref. 7)

Insolublc - no hydrolysie

A procedure for preparation of pure T was reported in 1948 (Ref. 3l) in which T was produced
by the action thionylchloride in chlorofonn or in dimethylalamine on the hydroxyl corresponding to agent

T IIO(qH.SCrIIIOH)J].

The hydroxyl, whictr is non-vesicant, was obtained by the reaction of

dichlorethyl atrer with the sodium sdt of 2-hydroxyettranethiot. Pure T can also be produced by &e
photochemical addition of bis(p-mccaptoethyt)ether to vinyl chloride.

3.3.2

Preparation of Q

Agent Q was first prepared with the reaction of thionylchloride with the hydroxy compound
conesponding to the chloroethyl compound that is Q. The hydroxy compound was prepared by the
interaction of ethylene dibromide and 2-hydroxye0ranethiol in alcoholic sodium ethoxide (Ref. 26). Pure
Q has been prepared by the photochemical addition of ethanedithiol to vinyl chloride.
22

DOCUMENT UTVCIASS IFIED IJPON REPRADUCTION JCP.I, DPG

Table 14. Physical Properties of T utd Q.

a
Phvsical Shte et Room Temoerature

Liquid

Solid
-

Liouid Density

g/nl et 20'C @cf. 29)

t.2362llat tt 25'C (Rcf. 29)
1.24 gl4t rt 25oC (Rcf. a).
1.2311 g/mf rt 20"C @cf. 7)

1,24A9

Boilinq Foint
140'C (Bef. 7)

357.1'C (Ref. 29)

353oC

120oC et 0.02 mm Hg (Ref. a)

(crlculrtd) (Rcf. a)

Freezinq Tcmpereture

57'C (relting point) (Ref. 7)

8.97"C (Rof. 29)

lO"C (Ref. 4)

56-57 oC (Rcf. 4)

Viscositv
18.3 cP

rt 20oC (Ref. 29)

Surface Tension
,16.0 dyace/cm et 20cC (Ref. 29)

45.5 dyoos/cm

rt 25"C (Ref.

29)

Refrsctive Indcx
1.5394 et 2OcC (Ref. 29)
t.5173 rt 25oC (Ref. 29)

Lgtmt Heql of Fusion

4.65 kcel/mole (Ref. 29)

Letent Heat of Vaporizalion

l9.l

kcsl/Eole (Ref. 29)

Vapor hessure
0.1744 Torr rt 2OoC (Rcf. 29)
O.3O{4 Torr rt 25"C @cf. 29)

0.000013

nn

Hg rr 20oC (Rcf 4.)

0.@015 mm Hg et 20oC (Ref. 4)

Solubilitl in rileten
Inrclublc (Ref. 7)

O.3

gtt

Solubilitv in Solvents
Rcedily solublc in moct orgrnic solvcnts,
in elcohol (Rcf. 7)

less colublc

Volstilitv

0.94{3 nillimle/m3 rt 20'C (Rcf. 29)

0.16{2 millimolo/mr .t?5"C (Rcf. 29)
o.(mt rylt il 25"c @cf. 4)

0.0004 mglt rt 25oC (Rcf.4)

23

DOCUMENTU /ctAssIFIED U?ON RE?RODUCTTON JCp-t, DpG

A process for semicontinuous plant production of Q was reported in 1955 (Ref. 32). This
involved the reaction of 2-mercaptoettranol with sodium hydroxide and subseguently ettrylene
dichloride
to yield bis(2-hydroxyethyl thio)ahane or sesquiglycol, the hydroxy corresponding to
as follows:

Z-nurcapo- dtun
cthapl hy&ort&

2Nasq,tr.oH + ctcfl.Cl

IIoCStfCrttrSCSt.OH + 2Mact

?tbhru-}

sesuiggr;ol

diclloride

The sesquiglycol, in the presence of dichloromethane, is chlorinated by phosphorous trichloride,

to yield Q as follows:

Hoctflgct|I.Sczllpfl

saqutstycot

ffi
Pce,

'*'"",

o!ffi*#

cecprscsttsctll.ce + p(olrrtct
asc,tt

the sesquiglycol, in the presence of ethyl ether, is chlorinated by thionyl chloride to produce Q
follows:
-or

as

"*t;
(cHst)2o

vquistycot liilHk

ascnt Q

In another 1955 report (Ref. 33) several procedures were described for preparation of Q

as

reported by various investigators. A procedure whereby sesquiglycol was chlorinated with phosphorous
trichloride in the presence of methylene chloride was suggested as a potential method of preparing large

24

DOCLJMENT UNCLASSTFTED tJPoN

Table

15.

Lthal Elosage of H,

nep?99U9!98 ,tSt!,

T,

and Q for Various Animals

Eef,

a).

Agcat

(ng.miald)

(ry.nin/nP)

Mottcc

8@ - 4,140

r70 - 270

Rrt

E4O

- 1,512
1,700

400
> 1,600

900

- I,uls

2,000

Guincr Pig

Rrbbit

Crt

700

Dog

6m

Gort

1,9(X)
800

Monloy

I{Cr)50

L(Ct)50

Ucr)50

Aninel spocicr

(ng.Ein/n)
774

- \650
a

900

,,1

'No dstr

Table

16.

Effect of Chamber Airflow Rate on Lethd Dosage for Vesicant Agents

to which Mice Are Exposed (Ref. 4).
L(Ct)50

Expocurc Tlpo

Airflow

Totel Body
(body plus inhalrtion)
Body Only Exposurc

(hcc protcctod)

Inhrl4i66 EXpoeisc
(body prot*tcd)

Table

17.

(-H
T
o

Reto

Low
High

1,200
1,400

170

lm

Iow

3,5m

l,5oo

High

3,4(X)

510

I-w

1,6(x)

280

Hish

1,6(X)

2r0

Relative Vesication Resulting from H, T, or Q Deposited on Human Skirr (Ref. 4).

Vepor
Ptrssurc
H8 rt

Agart

(ag.lnidm)

20oc)
0.75

0.m015

0.000013

rlin rnr
oovcrcd or
'Thc
I Q dinolvod incithcr
dioxrno.

Modian
VesicrtinS Doso

Vesicetim
Rclativo to

Vesicrtio Roletivc
io H (H=11

H (H-100)

0.g)
(Not Covcrcd)

(Covcrod)

32
4
0.3b

100

ll

<100

<l

100-2m

not sovcrGd during cxpoture.

26

Not Covcrod

DOCUMENT U'VCLASSIFIED UPON REPRODUCTION JCP-L DPG

3.6

THERAPY AND PROPHYLAXIS

There ue no prophylactic measures available for mustard intoxication by sulfur mustard agents
other than physical protection afforded by protective masls, clothing, shelters, and ointment (M5).
Protection, fust aid, and therapy for erynsure to mustard on the battlefield are covered in U.S. Army
Field Manual t-2E5 (Ref. t8). In generd, therapy and prophylaxis for sulfur mustard agents are identical
to those for nirogen mustards given in Section 2.7.

3.7

EMPTOYMENT

There is no indication that T or Q have been employed as CW agents in a military conflict.

Although field test data were not found, it is apparent that freld testing for Q, which was to be
disseminated by thermal generators, was planned. Preliminary investigaion showed that dissemination
of this solid particulate by a thermd generator resulted in some decomposition of Q with resultant
production of
The oxic cloud dispersed from a generator would contein Q paniclx and H vapor
(Ref. 30). The anticipated use of the particulate wat as a barrier agent that would be deposited on terrain
or equipment to which access is to be denied, or at least to whiei asoess is arained at a pendty. The
hazard would have to be one of contact or aerosol because the vapor hazud from Q is nonexistent. A
produc'tion process for preparation of a mixture of Q and H yielded a uaterial conaining 25 to 30 percent
Q and the remainder H, along with some impurities. This material is more toxic, has a lower melting
point (about 5oC), and the volatility is lower than H. The mixarre, thus, has advantages over H or Q

II.

alone.

Employment, or plans for employment, of T in weapons have not been found. However, the
procedure that produced T as a contaminant in the producion procedure for H yields a mixture of H (at
the 95 percent purity of HD) and T at ratio of 60:40 (Ref. a). This procedure was used by the British
during lVorld \Yar II in plurt production of a mixed agent desiguted IIT. The product is a viscous liquid
with a boiling point above 2E"C, a fteezing point near 0oC, and a volatility slightly less than that of HD.
Data for toxicity indicated levels of toxicity in some laboratory animals $eatsr than that of HD, for other
animals, less than that of HD. The principle adyantage of the HT mixture over HD would be for
employrnent at a temperature below the freezing point of HD, that is, below about t5'C. With liquid
deposition on a target, the H component of the mixture evaporates first, leaving an agent T residue,
which, due to its persistency oow volatiliry), presonts a long-tcrm cioutact hazard.

It should be noted that in 1945, the mixture HT was approved as the fill for tbe 4.2-inch chemical
rnortar shell o replace agent L as fill for ttrat round. The 60:,lO HT mixture was, at that time, being
manufacturod in England and Cmada by the process described above. Agent for the 4.2-inch mortar
round was to be procured ftom Canada. It was evaluated as being superior to agent L (Ref. 3a).
Mortar rounds and 105-mm projectiles filled with HT are, at present, in the U.S. stockpile
chemical weapons and are slated for destruction (Ref. 35).

27

of

DOCUMENT UIVCLASSIFIED UPON REPRODUCTION JCP.I, DPG

SECTION

4. LEWISITE (L) AND MUSIARD/LEWISITE

4.t

CIIEMICAL COMPOSNON,dND PHYSICAL PROPERTIES

4.1.1

Intro0uction

(HL)

The compound designated as Lewisite has been known since 19O4 (Ref. 32). Soon after the use
of sulfur mustard by the German army in l9l7, rt least four different arsenicals were used, but were
viewed by th'C Germurs as leis effective thur sulfur mustard. These did not include 0re arsenical
designatod Lewisite. Lewisite was so named beause it was developed and promoted by Professor W.
Lee Lewis of Northwestern University, a captain in the U.S. Army in 1917. Due to its immediate effects
and apparent greater toxicity and incapaciu,tion capability on personnel than sulfur mustard, it was
considered a highly potent agent. Because the production process was suaightfonrard, a production plant
was built, production proceoded, and a shipment of Lewisite was enroute to Europe when the war ended
in November 1918 (Ref. 4,7, t6). In U.S. defense literature, Lewisite is frequently designated M-1,
puticularly in literature published during and immediately following World War II.

4.1.2

Chemical and Physicd Properties

The chemical struchrre and properties of L and HL are listed in Table 18. The physical properties
of these egents are given in Table 19.

4.2

CHEMICAL REACTIONS OF LEWISITE

Lewisite, as synthesized, occurs as a mixture of cis and rrans isomers. Samples of each form
were obtainod by oxidation to the corresponding acid, then purifred by recrystdlization and reduction to
yield the respective pure cis or trans isomer. The toxicity of the two forms is essenrially identical so
there is no particular military advanuge of one over the other. They do differ in most physical
properties; fteezing point for the cis isomer is reported x 44.7"C and -1.2'C for the razs isomer. The
physical properties given in Table 19 are for the mixture.
The hydrolysis of Lewisite is rapid and involves several rcversible reactioru (Ref. 32):

Iast

dCfllsCl, +

2H2O

ClCdIis(OH)z

slow

ClrCfllsoH,

Tf Hp +

2HCt

slow

aCfly'sO Tr (ACflrasQx
(oxidc)

(gemlnal dioA

(polyner)

The oxide is mildly toxic and vesicant, and it is not further hydrolysed in acidic solutions. It is
nonvolatile and iruoluble in water; thus, it separates from water. The polymer of tho oxide may form
hard insoluble lumps (Ref. a). In aqueous solution above pH 10, the oxide formed by the hydrolysis of
29

DOCUMENT U'VCLASSIFIEO UPON REPRODUCTION JCP.I, DPG

Table

lE.

Chemicd Structure and Pro,perties of

and

HL.
HL

Chemical Neme

Dichloro{2-chlorovinyl)rrsine +
bie{2-chlorocthyl)sulfidc (Rcf. 3)

Dichlom-(2<hlorovinyl)$8iDc (Rcf. 3)
Chlorovinyl rnino dichloridc @of. 3)
2-Chlorovinyldichloro rninc @of. 3, 7)
Dichloro-2+hlorwinyl rnino (Rcf. 5)
Chloroothcoyl rreinc (Rcf. 7)
2-Chlorovinyl rrsiac dichlorido Eof. 7)
0{tlorovinyl dichloro$sinc (Rcf. 7)
Chemical Stnrcture

CICH

2 +

- cg-nr/
\

crcH

I
- CH-As

ct

Chcmicel Formule

cJtcr2s + c2llrAscr'

C2II2AsCrz

Molcculsr Vl,cirht
207.35 (Rcf. 3)
20?.32 (tuf.s)

186.4 (Rof. 3)
It6.8 (Rof. 37)

@utetic Mixturc)
Ratc of Illdnolvsis

Vcry Repid
Hydrolvsis

Rspid

Mucts

(Acidic)
Hydroclloric ecid, thiodiglycol, end

(Acidic) (Ref.
Hydrochloric rcid end chlorovinyl-

rrscoou oridc

chlorovinylereoaous oxidc

@rsic) (Rof. 5)

@asic)

In dkelinc rolution thc oxidc hydrolyses

rs showD for L @ef. 5)

Acctylcoc
Sodiua rrccortc

Odor
Gerlic

Gcrrnium

Lewisite, yields acetylene and inorganic arsenite, which are nonvesicant Eef. 36). Chlorine reacts with
Lewisite in the absence of water to yield arsenic trichloride and dichloro*trylene.
Lewisite and Lewisite oxide in aqueous solution are oridizd by a number of oxidants, including
chloramine, to yield 2-ctrlorovinylarsonic acid. They are slowly oxidizd in fresh water, sea water, and

soil. The product, 2-chlorovinylarsonic acid may produce no physiologicd effects, or may be very
slightly toxic. Oxidation beyond the acid is not readily achieved Eef. 4).

30

DOCUM ENT U'VCLASS IFIED UPO N REPRODUCTION JCP.I, DPG

Table

19.

Physical Properties of

and HL.

HL
Phvsical State

rt

R.oom Tcsnprrturc

Liquif

Uquid

DElsltv

Liquid

l.t1

glmt rt 20cC (Rcf.

g/nf

1.66 glml at 20oC (rpprox.) (Ref. 3)

1.625 glmt (4.4% H, 59-6S L) et 25"C (Ref. 37)
L.575 gln.t (50:50 mix) rt 25oC (Ref. 37)

3)

et 25oC (Ref. 5)
1.92 gln.l et OcC (Rcf. 29)
l.tt76 jlme $ 20"C (RGf 29)
1.8793 glmt
25'C (Rof 29)
1.t542 glml 40'C Eof. 29)
1.88

t
*

Vrpor @clrtivo to rir) 7.2 Ecf. 5)

6.5 (Rof 5.)

Boilins Point
Bclow l90oC (Ref.3,37)

l90oC @ef. 3, 5)
195.9"C (Ref. 29)
Dcomoosition TemDereture
Abovc 100'C (Ref. 3)

Abovo l00cC

Freczim Tfrnlrersturc
-18

.42oC (plant production) (Rcf. 3, 37)

-25oC (antetic mixture) (Rcf. 3)
-25,4oC (eutoctic Eixture) (Rcf. 37)
:7.45oC (50:50 nix) (Rcf. 37)
-21.6"C (6O:40 L to HD) Ecf. 37)
-54.5'C (70:30 L io HD) (Rcf. 37)

O.loC (dcpcnding on purity)

(Rcf 5, 29)

Flash Point
Elocs not flash @ef. 3, 5)

High (rssumod) (Ref. 33)

Viscosity
2.19 ($.4fi H259.6fi L) rt 25'C (Ref. 33)
3.10 (50:50 nix) rt 25'C @cf. 37)

1.09 csr rt 25"C (Raf. 5)

cP gt 20oC (Rcf. 29)
2.W53 cP rt 25oC (Ref. 29)
1.595 cP at l()'C @ef. 29)

2,89

Surfece Tercion
44.2 dlaes/co et 10oC
41.8 dynoc/cm et 20"C
4l.l dyncs/co et 25oC
39,3 dynedcm rt 40oC

(Rcf. 29)
@ef. 29)

(Rcf. 29)
(Rcf. 29)

Rdrac{ive.Indcx
1.6201 .t OoC (Ref. 29)
1.6101 et 20oC (Ref. 29)
1.6076 rt 25oC (Rof. 29)
1.6001 rt 4OoC (Ref. 29)

3l

o c U ttt E N r

19.

Table

tF t E

UP o

N n e p n o D,? c T! o

Phvsical Prooerties of

and

IIL

urvclA ss

WP ! ;!t,P*lS )

(Cont'd)

HL
Latent

Hat

of Yrmrizrtion

58 cel/g ftom 0"C to 190"C (Rcf. 3, 5, 37)

15.8 kcrl/nolc rt 20oC (Rcf. 29)
15.5 Lcrl/mlo rt 25"C (Rcf. 29)
14.5 kcrl/mols il 40oC (kf. 29)

Vrmr

h,cssurc

3)
3)
Sl-

mn HX u lO:C ($:f._3)
0.248 mm--Ilg et-20'C{Rcf.-3)
l'03 mn H3-et 4OoC (Rcf' 3)

0.087 nm H3 rt 0"C (Rcf.

0.394 un Hg et 20oC @cf.
0.58 mn ttg-u ZS'C fi.f.

0.O2

+ O0 Torr at 2O"C (Rcf. 29)

0.35 + fi) Tor.t 25"C (Rof. 29)
0.12 + 0l Torr rt 40oC (Rcf. 29)
O.22

Solubilitv in Weter

jlt

36)

Quilc i$olublc

(Rof.
0.5
Insolublc (Rcf. 3)
Slightly rclublo (Rcf. 5)

Solubilitv in Other Solvents

dl commn orgmic rclvcots, in

oils, .od in mu*rrd and othor chomicrl egeots
Solublc ia

Solublc in or3rnic rclvcntc

Volatilitv

3)
3)
fi

2S

l,(Xi0 ng/mr rt OoC (Rcf.

4,480 E8/m! d 20'C (Rof.
8,620 ui/mr et 30cC fnof.
6.5 r ld m3/m'et 25"C (tuf. 5)

mglm,t qt

-1!'C @ef. 3)

et 20'C-(Rcf.-3, 37)
lJl-!-urild
lo,27o E8/d 40'C (Rcf. 3' 37)

Chlorinationof Lewisite in water yields tetra$loroarsine, which is unstable and oonvrts in water
to the arsenic acid. Chlorination yields relatively nontoxic products Eef. 7). Lewisite is corrosive to
duminum, but does not react with high-qudity steel, so storage in steel containers will prcserve thc
qudlty of the agent indefinitely. For storage in iron, sabilizers must be'added to ilre agent.

4.3

PREPAMTTON OF AGENT

4,1.1

Preparation of Lewisite

The original procedure for preparation of Lewisite war the reaction of acetylene uichloride
catalyzed by aluminum chloride as follows (Ref. a):

l2

DOCUMENT UIVCLASSIFIED UPON REPRODIJCTION JCP-\, DPG

(L-1)

CJI,
(CEH

CI{$sCt

(L-2)

(CICH -CI{) yls

(L-3'.)

->

The above materials, L-1, L-Z and L-3, are the primary, secondary and tertiary dichloroarsines
that have beeo designated Lewisite A, B, and C or l, 2, and 3. Lewisitg A or I is the compound
designated pure Lewisite, and the one sought in the preparation process. In the above procedure, I tar
residue and an explosive materid were dso formed. The product of this procedure contained only 20
percent Lewisite (that is, L-l).
Subsequent

o World lYu I, other procedures were examined, panicularly the use of other

catalyss. It was found that one of the.best catdysts was cuprous chloride used with ethanolamine
hydrochloride to yield a relatively clean product. Mercuric chloride was also used effectively. Work
was undertaken during World War II to dwelop an inexpensive process for preparation of arsenic
trichloride. It was found that crude arsenic trichloride recovered ftom ore of the Gold Hill, Utah, deposit
could be converted to highquality arsenic trichloride. The procedures were used during World War IL

4.3.2

Preparation of HL

HD and L are mutudly miscible, various HL mixtures could be prepared for use in
different environments below the fteezing point of HD (15'C) by taking the advantage of tlre greater
toxicity and persistency of HD. A eutectic mixture of HL with a freezing point of -25oC could be
prepared by mixing 63 parts of L with 37 parts of IID by weight or 56 parts of L wi0r 49 parts of HD
Because

by volume (Ref. 38).

4,4

SYMPTOMATOLOGY, PATHOLOGY, AND MECHANISM OF ACTION

4.4.1

Lewisite

Contact of Lewisite liquid or vapor by skin or eyes causes immediate pain that is rnore intense
than that caused by sulfur mustard. Visible irritation of the conjunctiva and complete elosing of eyelids

hour or less after contact, depending on agent concentration. Pain from skin
contamination begins as a stinging sensation and progress* to deep, aching pain. Liquid contamination
causes a grey area on the skin within 5 minutes, followed by erythema similar to Olat caused by sulfur
mutard. Blisters deeper than mustard blisters develop in about 12 hours. Exposure of skin to vapor may
result in erythema, but seldom in blisters. The vapor concentration re4uired to produce blisters is beyond
a field capability. Pain accompanying erythema persiss for 2 or 3 days. Severe skin lesions resulting
from Lewisite burns will usudly heal in 18 to 30 days. Fluid occurring in Lewisite-produced blisters is
nontoxic, but does contain some residud arsenic. The response to a drop of L as compared to a drop
of H deposited on the human forearm and the progressive course of effect is shown in Table 20 Eef. 7).
occur wittlin

33

D O C U M E N7

Table

20.

UNCLA SS

Sequential Effect

tF t

E D U p O N R Ep R O D U C T t O N

J_C

p
:1.,_

p. r_G

of One Drop of Liquid Lewisite or Sulfur Mustard on the Skin of the

Human Forearm (Ref. 7).

Tine

Lcwisits

Sulfur mrtstrrd

At rpplication

Slight buruing

Nothing

Drop corylctoly diffusod inio thc skin

Slow rosorption

Dovclopmcot of resh

Not yct complctc rccorption

Surning rud rpread of the resh

Nothhg

Edpmr; rcddcnd rrer stends out

lr{sthing

135 Ein.

Dlrk rcd colorrtion

Slight spotty rcddcning

195 Ein.

Sevcrc burniag; resh eree 12

270 EiD.

Incrcrsd b,urnirg

315 EiE.

Focru of infleomrtion 3

of tho drop

Aftor: 5 min.

t{ rnin.
lg min.
105

Eh.

Ycllowish-red coloretion

15 cm

No acosrtious

tircs rs lergc rs

of tho mudrrd

Pronouncod resh; discoloration rs intc,nsivc as

thet of thc l-ewisilc

Tigsuo swells

Edcmetous srlclling; pcriphcry wall-like

Cbcrry-d blistrs in the ccnter, surrounded by

tiny blistcrs

Focus of inflemmetion merkcdly differcntiatcd

from hcdthy tissue; rpd rrpg eround penphery

900 min.

Blistcrs nrn togother; blistcra ycllow in color

with 8ltoish tingc et thc edgcs

Sbrrp demrrcrtion from healthy tissue; no blistcr formrtion; inflrmmrtion yellowish white

uh

Ono lrryo blistcr hrs formcd from dl tho blieton (12 cm lon3, 7 cm widc, 4 cm high); stin
tiraro eround il intcnsoly rd, pufi

Formrtion of blistcn rt thc pcriphcry (bcedliko); blistcm nra togothcr

32b

Blistcr cmptics contcot; whitish ycllow fluid

Blirtcr upon blister; blislor field is pale

Surfrce whorc blisicr hrs bccn removed is red

rnd inflemed

Blistcrs bocomo less svollen; still no blister

Surfrcc of wound has e dirty yellow coatiag

Littlc chenge; erm is edemrlous and swollen

Purulcnt socrction decrcrsas

Blisters further inclined 0o fl&tten out ar8

eround the infleometion much rcddened

6th dey

Hceling begins

PiSmotstion (purplc) of tho surrouding rrca

tth dry

Scpention of wouod nrrfecc; slight blccding

Pigmtetioa bccomes &rkcr (browa)

l0th dey

Progrres in hceliag; where blieter slcin is not

rpmvod contcnt of blistcr hes &ied up

Blislors bred< cesily; spread of pigneatrtion

Coutinuod oloughiag off of necrotic tiesue;

whcrp blistcr slcia not rcmovod, poriphcry

Un&r tho fragile epidermis exteosive tough,

clinging ucrotic rrlssa

360 min.

7t0 min.

On:
2nd dey

3rd dey
4th

&y

12th

&y

thet

formrtion in ccntsr

blrckish
14th d8y

Progrcss in hoeling; blister rlrin flalos off,

lerving hodthy slcin bcncrth

15th to 20th

&y
26th dry

it

Vcry eovoro nccrotic dogoneration

Skin growing over; Bom nocrotic foci in center; letor heeling; lcnde,ncy !o dcvclopmnt boils

Culminstion ef demegci necrotic degenerations

hrvc incrcesad

HGdd

Nerotic tieruc bas not yct bocn sloughcd off

34

DOCUMENT U/VCLASSIFIED UPON REPRODUCTION JCP-\, DPG

Mild intoxication of the eyes will persist for a few days, whereas seyere intoxication of the eyes,
particululy wih liquid agent, may result in permanent injury and blindness. Inhalation of vapor produces
immediate pain aud serves o give an immediate warning of the presence of the agent. Exposure causes
lesions in the respiratory passages. Coughing and nasal secretions will occur, and fluid may accumulate
in the chest cavlty.
Lewisite has not bem used by, or against, the United States in combat, and there are no recorded
human deaths from exlnsure to Lewisite. Thus, pathologicd rnanifestations of Lewisite intoxication in
man have not-been described.
Absorption of Lewisite liquid or vapor through the skin of dogs may cause death in less than 48
hours as a result of shock associated with loss of circulation fluid. With small nonfatal doses, vapor or
liquid inoxication by Lewisite througb the skin or by inhalation will canse hemolytic anemia, necrosis
of the liver and the biliary passages, and injury o the intestind muoosa. hilmonary edema, restlessness,
weakness, subnormd tempersilre, low blood pr6sure, and diarrher mey accompany severe Lewisite skin
burns (Ref. 4).

The mcchanism of Lewisite action is not known. There have becn assurnptiors, based on the
similarity of symptorns to that of mustard agents and the presence of chlorides, that Ore mechanism is
similar to fiat of mustard (Ref. 17). However, there is little basis for this assumption in terus of
experimental data, or on a theoretical basis. A reasonable assessment, basod on curent knowledge, is
that the biochemicd mechanism of the oxicity of Lewisite is distinct from thet of sulfur mustard. This
can be, in part, based on the antidotal effectiveness of British Anti-Lewisite (2,3dimercaptopropanol;
dimercaprol or BALI and other dithiols in chelating the trivalent arsenicals and comp*itively reversing
the chelation reaction between arsenic and the critical thiol groups of enzymes. However, BAL has no
effect on, nor does it relate in any sense to, the mustard agens Eef. 10).
It was early observod Eef. 39) that the action of Lewisite (and other arsenic compounds ineluding
Lewisite oxide) resembled the action of iodoacetate on the pyruvate oxidase system, and 0rat cysteine and
glutathione were competitors of the thiol groups of the pyruvate oxidase system for the iodoacetate or the
arscnicals. Howevetr, the comptition of these monothiol compourds, ttrat is, cysteine and gluathione,
was insufftcient to completely arest Ure effect of ttre arsenical on the pynvete system. A search was
undertatm for a dithiol that would form a stable ring with the trivalent arsenicd Lewisito. Several
dithiols of low molecular size were synthesized and tested, including BAL.
Parenteral adminisuation of BAL within 2 hours of skin exposure to Lewisite prevented not only
the skin effects of Lewisite, but the systemic effects as well. Howwer, Ore effert of a single treatment
with BAL did not provide continuous protoction. Injection of BAL et 4{our intervels fot 24 hours, and
less frequently at reduced doses thereafter, provided adequate protection. BAL has adverse effects on
various tissues, probably intorfering with cellular respiration and with m*allic respiratory requirements.
BAL not only reacts with arsenicals, but has been effective in preventing and reversing the effects of
other heavy metals on enzyme systems (Ref. a0).

A recent review of literaure (Ref. 17) directed oward waluating Lewisite and mustard

agents

as causes of delayed action debilitating and potentidly fatal diseases, particularly cancer, presented the

35

DOCUMENT UNCLASSIFIED UPON REPRODUCTION JCP-|, DPG

general conclusion that too linle information was available to establish a cytogenic and mutagenic effect
of Lewisite on animal tissuo.

4.4.2

Agent

HL

Limited experimental data indicate that the symptoms resulting from HL intoxication reflect ilre
of each of the agents constituting the mixture. Thus, immediate irritation of the skin
and eyes result from liquid or vapor contanrination of those orgarr, as expected from Lewisite
inoxication. Pulurcnary exposure mry produce derna in the respiratory muoosa and fluid accunulation
in the ctrest ririvity. Blister cliaracteristics reflcct those associated with eath agent. The protection
afrorded by rapid hydrolysis of L in contact with surface body fluids associated with lacrimation and
sweating will be negated by the mustard present. The contribution of each component of the HL mixore
to the toxicology of HL hu not beil differentiated Eef. al).
symptromatology

4.5

TOXICITY

The toxicity of L in terms of the lehal dosage for laboratory animals where the entire body
(unprotectod respiration) is exposed to L vapor is given in Tablc 21. Data are ftom multiple exporimental
sources. In Tables 22 ard 23 dau of toxicity for animals under desigruted exposure conditiors are given.
The ldhal dose for man is estimated from animal exposure data obtained primarily during World War
tr. Estimates published since are not different from those published at that time. Estimates of toricity
for man are presented in Table 24.

Table 2I.

AriErl

Toxicity of L for Animals when the Entire Body Is

Exposed to Agent Vapor (Ref. 4, 5).
Durrtion of Exposurc

qc0s0

(nin)

(mg'ninlf)

10

0.9 - 1.4
2.8

Mousc

l0
t0

1.5

2.5 - 2.E
0.5

10

9-14
9 -25
60

Rrt

1.5

- r80

0.58

9-25
60

1.5

- lEo

0.5t

9-14

1.0

5-180

0.57

7.5 - 13
60 - 310

t.2

Goet

100 - 255

r.25

Dog

7.5

- 1.5

1.4

Guinor Pig

Rrbbil

1.5

36

DOCUMENT UruCLASSIFIED UPON REPRODUCTION JCP.I, OPG

TableZ2.

Toxicity of L for Animals when Exposed

Duntion of

Coadition

Exporure

L(C050

(nin)

(mg.Ein/f)

10
10

1.2 - I.9
0.3

l0

7.0

Herd Protcctd

Monso

Vapor (Ref. 4, 5).

Inhdstim

- 1.5
1.6

1.4

10
10

l0

1r-5

9 -25

20.o

l0

15.0

Ctt

30-45

30.0

Do8

30-60
l0

30.0

R,;

Hed Protectd

Rrbbit

Table

,10.0

23. Toxicity to Animals of Percutaneous

Application of Liquid L (Ref. 3, 4).
LD5O

(mg&g)

Animel

r5

Monss

t5-24

Rtt

5-6

Rrbbit

t2

Guince Pig

Table 24.

Dog

38 - ce.70

Gost

to-24

Toxicity of Lewisite for Man @ef. a).

Vrpor I{Ct)50

Liquid

(ag.nlirilt)

(ne)

Level of lntoxicgtion

Derth by inhqletion
Dcrth by pcrcutanoous exposure
Vcsication of cxposcd ekin
Scrious comesl &mage

1.2

L.5 (estinated)

100 (estinaled)

2t00 (mtinatod)

t.2 - 1.5

o.014
0.05 - 0.1 mg/cmz

1.5 (estimeted)

0.1 (cstiustod)

37

DOCUMENT UruCLASSIFIED IJPON REPRODUCTION JCP.I, DPG

It is not litely that better drta on toxicity for man will be obtained, but the data presented do raise
questions.
some
For example, the inhalation lethal dosage for man in Table 24 is no greater thur tha
for mouse in Table 22. One publicuion gives a vdue of 6 mg.min/f as the dosage required to produce
lesiors on bare skin exposed to yapor, as comparod to the value givm in Table 24. Other reported
dosages @ef. 7) are 1.5 to 2.5 mg.min/t as an LD50, 0.15 mg.min/t to produco cye inflammation, and
0.75 mg'min7t leads to severe incapacitation.

4,6

PROPHYLAXIS AND ITIERAPY

4.6.1

Prophliaxis

There are no prophylactic measures for protection against ur sttack with Lewisite other tltan
physicd protection afforded by protective masks, clothing, shelters, and oinrncnt (M5). Protection, first
aid, and fterapy for exposure to vesicants on the battlefield are covered in U.S. Army Field Manud
E-285 (Ref.

lt). The vesicant agent protective ointment Mli is a white substance containing drloramide

5-330. It is

for epplication to the skin to protect against aad neltrdizc vesicant agent
If, subsequent to contamination of the skin by Lewisite, BAL ointment is used, the M5

intended

contamination.

ointment should be completely removed first as M5 ointment

will inactivate BAL.

First aid involves removd of evident droplets of liErid agent on skin or clothing by lifting off or
bloning, followed by the application of decontaminant pads and powder.
Liquid contamination in the eyes must be rernoved immediately, within seconds, by irrigating the
eyes with water from a canteen or other clean water supply. In a contaminated area, this should be done
while holding the breath bgween doffrng and donning the mask. Tearing of the eyes should also be
encouraged as this will minimize the effect of agent L.
Contamination by Lewisite is distinguishable from mustard contamination because of the
immediate strnging and pain sensation in skin contaminated by Lewisite. This sensation should illicit an
immediate response to decontaminate and take subsequent measures appropriate to Lewisite intoxicuion.

4.6.2

Therapy

Application of BAL ointment to areas of skin contaminated by Lewisite should be made as soon
prior to appearance of any vesication. The ointment should be applied in a thin layer and
removod after 5 minutes. BAL has some adverse effects on tissue; therefore, it cannot be applied u a

as possible,

contamination preventative.
Erythema re4uires no specific treatment and will heal in a few days. Blisters should be treated
as therurd burn blisters. Large blisters and blisters on the face should not be bandaged. Itching may
be treated with calamine lotion or steroids. Open blisters might require use of burn creams to prevent
bacterid infection. With severe blistering and penetration to subcutaneous layers, treatrnent for shock
may be required by adminisEation of electrolytes.
Eye intoxication is treated with eye ointments. Pain is alleviated with morphine or other systemic
medication. A drop of atropine three times daily will aid in alleviating pain from severe photophobia ud
38

DOCUMENTUIVCLASStFtEOUpONREqRODUCTIO!!C!'_-!!9?*G

blepharospasm. Sulfacetamide may be applied to control infection. Pressure of dressings on the eye
should be avoided.

No experience with respiraory involvement fiom kwisite exposure in man has occurred. It is
assumed that effects and trearnent will be similar to that of mustard, i.e., mild cases of respiratory
involvement are treatod symptomatically to relieve cough rnd mild pain, and antibiotic treatment may be
required if bronchial pnzumonia develops. Orygen adminisration and physical clearing of the respiratory

with extreme cases. Treahent of respiratory Lewisite intorication, as well

as eye and skin effects, may be benefited by pumterd injection of BAL/oil solution, which is indicated
for treaturent bf systemic effecti from Lewisite inoxication. A l0 percent solution of BAL in oil should
be administerod by injection deep into a buttocls muscle in accordance with the weight of the individual,
but not to excepd 4 mf . The injection should be repeated every 4 hours for a totd of four injections.

passages may be required

lnjections of BAL may cause physiological syuptoms including oppressionof the chest and throat,

burning sensation, muscular actres, mild nausea and possibly vomiting. These effects may appear within
15 to 30 minutes after an injection of BAL urd may persist for 30 minutes.
Since the therapy for mustard intoxication is indicated for Lewisite, the therapy
by agent HL strould not be different than that described above.

4.7

EMPLOYMENT

4.7.1

Employment of Lewisite

for intoxication

Agent L was produced and intended for use, but was not used, by the U.S. Army as a chemical
warfare agent during World War
It was, at that time, assumed that agent L would be more effective
agent
H.
This
assumption
was
thur
based on limited rxearch regarding the action of L on laboratory
animals, particularly dogs and rabbis, and on some accidental exposures of laboratory personnel. It was
observed that the lesions produced as a result of these accidents were deeper and more painful than
lesions resulting from H intoxication. Experimental work indicatod that rabbits were more sensitive to
agent L than H with regard to rnanifest skin effects, damege to eyes, and systemic response. However,
it was subsequently shown that the gteater response of rabbits to L, as compared to H, did not reflest nor
simulate the comparative effects of these agents in man. Dogs were about equdly resporuive to L and
H with regards to skin and eye effects, but more susceptible to.systemic response with agent L than with
H. The effect of L vapor on the respiratory system of the dog was twice that of agent H. It was later
ddermined that thE response of the dog to L as compared to H did not simulate the comparative response
of man. Researctr with agent L was not undertahen in the United States between World War I and World
War II; however, reports published in 1932 in Germany showed that agent L was inferior to agent H.

I.

Itr/ith entry of the United States into World lVar II, production of L was undertaken coincident
with research and testing in ttre United Sutes and England. Research during World \Var II of the effects
of L on Eren as compared to H, reversed the previous perception concerning the superiority of L. It was
determined that a comparison of a small dose of L with a like dose of H on human skin demonstratod that
L was more effective, but comparisons of higher doses of each agent showed that skin lesions in man
were much more severe, were more painful, and required much more time to hed with H than with L.

39

DOCUMENT U'VCLASSIFIED UPAN REPRODUCTION JCP-|, DPG

Field testing during \[orld War tr demonstrated that gmeration and maintenance of Lewisirc vapor
was not militerily feasible. An initial effective concentration could be achiwed only over a very smdl

minutes. Dissemination was tested with bombs and spray tanks. Agent L, thictened by
wls comparod o nonthicke,ned L disseminated ftom I spray tanlc or aircraft.
Droplets of nonthickenod L dissGminatd ftom spray tanls u 2000 ft above ground evaporate before
reaching the lround. Droplets of ttrickened L were deposited on the ground, but became hardened, whictt
roducod the effectiveness ofvapor releaso by droplets. Thickened L, when sprayed from an aircraft spray
tank at 200 fect above the ground, was less effective than nondickened L in producing casualties in goats
that were plac-+ on the gpound.in the targA area. The properties of thickened L and HL are discussed
in greater detail in References 4L ard 42.
area

for

a few

use of mettryl mahrc'rylate,

It was also found that banle clottring provided fairly good protection from L vapor. Additionally,
of the rapid hydrolysis of L, penetration of wet clothing did not occur. High atmospheric
humidity hydrolysod the agent. The principd hydrolysis product is Lewisite oxide, whictr is mildly
vesicating, and is nonvolatile. It is insoluble in water, but is degraded in dkaline solutions.
because

Agent L, in low vapor or liquid concentrations, is capable of producing incapacitating lacrimation

of the eyes, but the hydrolysis of the agent by tears is believed to effectively diminish the chance of
additional eys injury, ilcept at concentrations of agent above that anainable in the field.

As stated in a previous section, the HT was officially designated the chemical agent fill for the
4.2-inch ctremical mortar round, replacing L Eef. 34). This should indieate recognition of the general
unsuitability of L as a CIV agent. Howwer, the ease of L production and its suitability for use in a dry
climate agairut poorly rained and equrpped troops, may justiS concern for possible employment of it
by some nilitary forces.

4.7.2

Employment of HL

L mixed with tI arose primarily from a need to reduce the freezing point of agent H.
The mixture of L with H as Levinstein mustard yielded a material highly corrosive to steel and other
metal containers. The mirfire of L and agent HD yielded a product reasonably stable in storage. The
freezing (or melting) point of the L and HD mixhre, which will be assumed to be HL, is -25"C for the
e.utctic mixilre. A frcczing point of 42"C is reported for a producion plant product. The very low
freezing poiat of ttre plant product results from the presence of impuritix.. The H portion of the product
with this low freezing point is Lcvirstein mustard rather than HD (Ref. 43). Agent HL will serue as a
moderately effective blister agent for use at atmosphuic temperatures below ooC. At temperatures above
0oC, agent IIT may be more appropriately used. At temperahrres above l5oC, agent HD may be more
effective than HT, and is easily more effective than HL.
Tho use of

40

DOCUMENT U'VCLASSIFIED UPON REPRODUCTION JCP-|, DPG

SECflON 5. DEI'ENSE AGAINST CIIEIVTICAL AGENTS

5.1

DETECTION

A recent survey of the equipment available and the capabilities of detecting chemical agents in the
field is presentod in the Joint CB Technical Data Source Book, Volume XIII (Ref. aa). A number of
fielded chemical agent detectors, dating back several years, are discussed in that document. A brief
summary of so.me of those detectors is presented here.

a.

PaDer. Chemical ASent Daector. ABC-M8. This d*ector paper is a Canadian development,
the outcome of a joint ripartite endeavor. It was qrpe classifred in 1964. The paper d*ecs liquid agent
deposited on surfaces ard differentiat$ among H, G and V agcnts. The paper gives a color reaction after
it is used to blot a liErid rgent dropla on a contaminatod surfece. The M9 paper, dweloped rnore
recently than the MB paper, is in many respects inferior to the M8. It responds to liquid agent impacting
on the p8p9r, but does not detect mustard, nor does it identify agents it has detected. There is no

indication thu the M8 paper could be used to daect any of the agents discussed in this book.

b. Detector Kit. Chemical Agent. M256l256A1. The M256 kit war qpe classified in 1977. lt
d*ects and identifies liquid and vapor agent, but requires 20 minutes for detection. For vapor detection,
the kit contains a plaquette with the reegents needod to indicate the presence of all detectable agents. It
contains eight sampler/detectors for vapor and a bookle of 25 M8 papers for liquid daection. Thc kit
respottds to several qpical interfering battlefield vapors. This kit will detect L and HL and should be
able to detect T and possibly Q. tt is not identified as a daector for HN.
c.

Water Testing Kit- Chemical Agent- M272- This kit contains reaction tubes to test for blood
and blister agents and enzyme tickets o identify nerve agents. The kit weighs 2.5 pounds and contains
reagent for 25 tests for each agent group. This kit is assumed capable ofdetecting all agens discussed
in this book.

d. Chemical Agent Automatic Portable Alarm- Mt. The ME alarm has l0 variations, all based
on two basic components, the M43 detector and the M42 alarm. The origind M43 (and the follow-on
M43Al) does not detect blister agents. A current modification that was developed in response to interest
by the U.S. Marine Corps (Ref. 45), has, as an add-on to th M43Al., the capability to detect blister
agents as well as newe agents (Ref. a6).
e. Individual Chemicd Aqent Detector fiCAD). The ICAD is a small detector for individual use.
It detects nearly all known ehemical agents; howener it does not detect VX. In addition to individual usc,
it may bc used u a point, remote, or drop+ffsampler. It can transmit detection up to l0 km. It utilizes
olectrochemical sensors and distinguishes botween blister agents md all the other detectable agen6 as a
group. The electronic module has a S-year life span and ttre sensor a 4-rnonth span of continuous
It is uncertain if this detector would derect T and Q. Presumably it will detect HN and L.

f.

use.

Chemical Agent Monitor (CAM). The CAM is a hand-held monitor used to detect urd
distinguish contamination of blister or nerve agnts on surfaces. The CAM detects vapor emanating from
a surface when atmospheric temperature is in the range of 45 to -30'C. Its performance can suffer
4L

DOCUMENT UNCLASSIFIED UPON

JCP-|, DPG,
...@-....- REPRODUCTION

interference from high concentrations of sone comtilrn battlefield contaminants. The time to respond
to 0.1 mg/rr3 of musurd was 6 scconds. An upgrdc of the CAM is in pmgress. The CAM will
probably not detect T aod Q, but mary detect L snd HN.

g.

Standofr Remote Seming Chemicsl Agent Alann. XM2l. This man-portable unit remotely
detects chernical agent clouds at up to 5 km by maetrr of an infrarod spestroradiometer. Response time
is less than one minute. The unit cost of 6e X[Ol is projerted at $60 to $75 thousand, a cost that will

limit use of &e device.

eriiomitic Ctremicd l,tent p*ector ^Atanrr" XU22 (eCaOA). Tlre XN122 is an advanced
point sampling darm that identifies dl agenE at nerr minirnum detectablc levels in the presence of
interfering conteminans. Thk dae$or will probebly not detect T and Q because of the lack of
vaporization of these agents. Tte d*ection of HN is specifically indicated.

h.

5.2

PHYSICAL PROTECTION

5.2.1

Collective Protection

Standard physical protection agairut chemical warhre agents for U.S. military personnel is
available as collective protection and individual protection. Collective protection is provided in any
enclosed stnrcture that protects personnel ftom chemicd agent (liquid or vapor) and allows them to work
unencumbered by persond protective equipment. The key element of the collective shelter is the filtered
air circulating system. Collective protection systern supply the shelter with air that has passed through
activated charcoel and particulate filters. The charcoal filter adequately removes agent wpor. Most
pennanent stmcnrres can be converted to collective protectiotr if the air entering the system can be filtered
urd positive pressure within Ore structure mainuined. Some collective shelters in the U.S. military
invenory that would provide protedion from HN, L, T and Q are:

e.

Survivable Collective Protection System (SCPS). The SCPS is a modular, semi-hardened

construction da,eloped for tbe U.S. Air Force. It provides working space for t4 persons within a single

unit.

b.

Translortable Collective Protection System (fCPS). The TCPS is an inflatable strucnrre for
emergency use in the field. It provides a rest area or light work area protected from an external toxic
environment.

c. XM28 Simglified Collective Protection System. This system is composed of en inflatable,

airtight enclosure that is inflated inside the Tent, Extended Modular Personnel CIEMPER). The XM2E
system interfaces with othe,r systems, including the TCPS.

d.

M20 SimDlified Collective Proteetion Room Liner System. The M20 is an inflatable room
liner and is equipped with a protected entry and a filterod air circulation system.
Collective protection systems have been developed for use on ships and for various vehicles, such
as the Ml tank.
42

DOCUMENT U'VCLASSIFIED IJPON REPRODUCTDN JCP-\, DPG

5.2.2

Protective Clothing

With the introduction of chemical warfare agents in World War I, the need for a chemical
protective covering for the entire body was recognized, and impregnated clothing was developed. The
clothing of World War I through World War [I was impregnated with chloramides as protection against
mustard vaEir and, to some extent, against liquid mustard (Ref. a). The chloramides oxidized and thus
inactivated mustard and Lewisite, but are not effective against the nitrogen mustards. Charcoal-impregnated clothing material was investigated in the \Vorld \Yu II era. The charcoal in ttre clothing adsorbs
the agent valnrs, but does not cause decomposition of the agents. Special purpose protective systems

may be of iniiermeable material that completely encapsulates the wearer.- Current U.S. protective
clothing is composed of charcoal-impregnated material.
Battle Dress Overgarment (BDO). The BDO consists of gloves, boots, hood, helmet cover,
and a twoaiece suit consisting of a jacket that has a zippered front and pants that have a fly front and
zippered legs. The suit material is an outer layer of nyldn-cotton and an inner layer of charcoalimpregnated polyureftrane foam. The outer layer is water repellant. The gloves have a black butyl
rubber outer material and an inner glove of thin white cotton. The boos are butyl rubber and made to
be worn as an overboot. The helmet cover and hood are of butyl-coated nylon cloth. The hood is fitted
to an Ml7 series mask (Ref. a7).

a.

b.

Chemical Protective Outfit (CPO). The CPO is the current standard U.S. military protective
uniform. The CPO is a two-piece overgarment, jacket and trousers, and also includes overboots, gloves,
and hood. The overgarment is two layers; the inner layer is cotton cloth and is impregnated with
activated charcoal, and the outer layer is nylon/cotton twill in stardard camouflage pattems or solid olive
green. The hood, gloves, and boots are rnade of butyl rubber. The entire outfrt weighs 1.7 kg.

c.

Saratoea System Protective Clothing. The adsorptive component of this system is composed
spheres adhered between fabric layers. Configurations consist of the army ground crew
ensemble, the aircrew coverall, the light combat coverall, urd the under-coverall for ground crew. These

of charcoal

materials provide protection

to personnel in a mustard vapor environment and

against most liquid

contamination.

5.2.3

Chemical-Biological Protective Masks

A number of masks are available. Many of them are special purpose masks designed for use in
operating specialized equipment, such as aircraft. Two multipurpose masks are:

a.

Mask- Chemicd-Biologicd: Field ABC-Ml7- Ml7A1. Ml7A2. The

since the 1960s, wi0r interim modifications resulting in the tno successors.

Ml7

has been in use

b. Mask. Chemical-Biological: Mrt0- M42. The M40 multipurpose mask is used by army
infantry, while the M42 is designed for use in combat vetricles and differs some in construction.

+3

DOCUMENT U'VCIASS I FIED UPON REPRODUCTION JCP-|, DPG

5.3

DECOI\TTAMINATION

5.3.1

Intrcduction

Decontaurination of the agents discussed in this book may be accomplished by physical removal
of the agmt, by ne$ralization of the sgent by ehemical reaction, or by naturd decontrmination or
weathering, Physical removal can be by scraping away droplas or blotting with a blotting msterial. It
may be accomplished by washing and scnrbbing or with solvents. The chomicd decontaminanb are
dmost exclus_ively chlorine compounds that oxidize the agent. The decontemhetrts af,e applied using
standard deconiemination equipment

5.3.2

Standard U.S. Decontamination Equipment

a. M29l

Skin Decontamination Kit (SDK). This

tit

is carried by the individud and is inteoded

for decontamination of skin, but can be used to decontaminate individual items of equipment, such as a
small weapon, helmet, gloves, and mask. The kit consists of a pouch with packas of pads of
decontamination powder. The basic ingredient of the powder is a resin, Ambergard9 XE-555, whictr
absorbs and neurdizes ehemisd agents. The material is nontoxic and can be used around wounds and
the eyes urd mouth. The SDK is a replacernent for the lv{258A1 kit.

@.

This kit is used once only and discarded. The kit is a plastic
b.
care conuining foil envelopes. Three packets are marked DECON I WIPE and each contains a gauze
pad containing decontamination solution. Instructions are on the pack* and the container; Three pack*s
are marked DECON 2 WIPE and each conuins a glass ampoule of decontamination solution. This
ampoule is
be broken onto a ganze pad, also provided in the packet. This kit is intendod for
decontanination of non- facial skin, clothing, and other persond equipment. The solutions are poisonous
and carstic.

c. Dgcontaminating and Reimpregnatin&Kit. Individual. ABC-MI3. This kit contains a pad filled
with skin decontaminating powder (fuller's earth), two bags of decontaminating and reimpregnating
powder (chloramine), a capsule of dye, and a cutter to cut away heavily contaminated clothing. The
reimpregnating powder would not be effective against HN.

d.

Decontaminating ApDaranrs- Portable. DS2- 1 l/2-Ouart- "ABC-ll. tris apparatus is

of a pressurized nitrogen cartridge ud chamber o be filled with the decontaminant solution
No. 2 (DS2). It will deliver a spray of deconaminant to a distance of 2 meters. It is mounted on a rack
composed

on rmst vehicles and is intended for use in decontaminating military vetricles and crew-serviced weapons.
The ABC-Mll is being replaced by the M13 portable decontamination apparatus.

Portable Decontamination ADparatus (DAP). The Ml3 is a manudly operated device

ttrat conuins 141 of DS2 for decontamination of vetricles and crewoperated weapout. It is mounted on
vehicles, replacing the ABC-Mll, and is one-person portable. It has a manually operatod pump utd a

e. Ml3

spray hose and wand.

f.

Dpcontaminating ADparatus- Power-Driven. Skid-Mounted MultiDurpose. Nonintegrd.

S00-gallon. ABC-MI2AI. The ABC-M[2A1 is composed of a water heater, tank, pump, and personnel

DOCUMENT UNCIJcSSIFIED UqON REqRODUCTION,!CP-t, OPG

unit. It is a multi-purpose apparatus to include chemical decontamination. The decontaminant

in
used
the apparatus is usudly super tropical bleach (STB).
shower

g. Ml7 Lighhpeiqht Decontamination System- Sanator. The Sanator consiss of an air-cooled

engine, a water pump, and water heater. It has supplementary hoses, spray nozzles, a decontaminant
injector, and a shower apparatus. It dso may be provided with a 6000',liter collapsible water storege
tant.

5.3.3

Decontaminants

a.

Decontamination Solution 2 (DS2). Decontaminant DS2 is composed of 70 percent

diethylenetriamine, 28 percent dtrylene glycol monoahyl ether, and 2 percent sodium hydroxide. It is
e stendard decontaminant for decontaminating chemicd egents.

b.

FWer Tropical Bleach (STB). When freshly made, STB conains 30 pacent available
chlorine, but loses some chlorine content durrng storage. It is composed of chlorinated lime and calcium
oxide. The STB is stored dry and may be used dry or mixed with water to decontaminate surfaces
contaminated with mustard. This decontaminant is less effective than HTH (high+est hypochlorite)
against HN. It is a standard U.S. military item.

c.

High-Test Hypochlorite (IITII). Also calld high-tst bleach (IITB), HTH is cdcium
hypochlorite and is available as a dry solid. It is water soluble. A decontaminating solution should
contain 70 percent HTII. The available chlorine is greater 0ran in STts, and it is more corrosive.

d. West German Material/Terrain Decontaminant (WGD) C8 Emulsion. This dccontaminant has

been tested extensively in 0re United States and is includod in the North Atlantic Treaty Organization
(NATO) inventory. It contains 15 porcent perchloroethylene, 8 percent calcium hypochlorite, I percent
emulsifier, and 76 percent water. It is mixed at the time of use. It is specifically identified as
decontaminant for agent GD, but is also effective in decontaminating mustard.

(ASH). ASH is a water-based solution of 0.2 percent cdcium

hypoctrlorite and 1.5 percent detergent in water, buffered o a pH of 7.53 with sodium dihydrogen
orthophosphate ard codium monohydrogen orthophosphate (Ref. 48).

e. Activatd

f.

Sodium Hloochlorite

Selr r imiting Activated Solution or Hylnchlorite (SLASHI. Slash is a water{ased

decontaurinant composed of trro solutions that are mixed at the time of use. One solution is composed
of 0.1 percnt cdcium hypochlorite, 1.0 percent detergent, and 98.9 peroent water. The oths solution
is 2.0 percent sodium citratc dihydratc, 0.4 percent citric acid monohydrate, aud 97.6 perccnt water. Tte
final solution should have a pH of 7.4. The mixed solutions should have a decontamination effectiveness
half-life of 2 to 3 minutes. SLASH was developed to limit the corrosive action of the oxidizing agent
by using a low concentration of chlorine, increasing the effectiveness by controlling the pH, and limiting
the effective life of the decontaminating ingredients.

g.

MEA. MEA is ordinarily made up as an aquoous

I percent (w/v) nonionic surfacant.

monoethanolamine and

45

solution containing 10 percent (v/v)

DOCUMENT U/VCLASSIFIED UPON REPRODUCTION JCP-|, DPG

5.3.4

Decontamination Effectiveness

Specific data applicable to the effectiveness of the standard decontaminants in decontaminating the
agens addressed in this book have not been found. Spme difFrarlty may arise with these agents. The
insolubility and nonvolatility of T and Q will contribute to prolonged persistence of these two agents.
Since Q is a-solid at atrnospheric temperatures, its removal from surfaces by physical means should be

facilitatsd. Agent

T is less reactive with several chemicals

than is

H, urd may be less readily

decontaminated than H.

The niirogen mustards'do not oxidize readily, but are decomposed-by some chloramides, by
calcium hypochlorite, and in dilute solutions of sodium hydroxide.
The nitrogen mustards hydrolyse in water, yielding toxic products at neutral pH and nontoxic
products in alkdine solutions. Decontamination of HN-l by MEA is preferred.
Agent HN-l in seawater at 25oC with a pH of 7.88 is reported to have a hdf-life of 1.5 minutes.
Hydrolysis of the toxic products derived from HN-l is estimated to have a half-life in seawater at 5'C
of 12.5 days (Ref. 49). Lewisite is decomposed to yield sodium arsenite and acetylene by aqueous
sodium hydroxide. The reaction with bleach has not been fully characterized. The hydrolysis of Lewisite
in seawater is very rapid, apparently yielding a pentavalent oxide of low toxicity. A problem with
decontamination and decomposition of Lewisite is the toxicity of residual arsenic. The question with
regard to use of L as a CIY agent and the resultant impact of the residual arsenic in the environment may
relate to fte degree of increase over the ubiquitous occurrence of arsenic in nature (Ref. 36).

5.3.5

Decontamination of Water

Lewisite hydrolpes readily to form Lewisite oxide, which is vesicant, insoluble in water, and
persistent. It is of concern in the contamination of water. The nitrogen mustards are also of concern as
toxic contaminurts of w&ter. The U.S. Army water purification unit, designated the Erdlator, was tested
in 1956 as to the effectiveness of removal of Lewisite (Lewisite oxide) and HN-3 from water. By the
use of large quentities of activated charcoal in the system, both of these agents were effectively removed
(Ref. 50).
The capability for removal of Lewisite or nitrogen mustards and their toxic derivative by reverse
osmosis has not been reported.

46

DOCUMENT UTVCLASSIFIED UPON REPRODUCTION JCP.I, DPG

SECTION

6.1

6. pEMTLTTARIZATTON OF CHEIVTTCAL

AGENTS AND MLJNITIONS

INTRODUCTION

The chemical agents presently in U.S. military inventory are under the jurisdiction of the U.S.
Army and are presently stored at seven locations within the continental U.S. and at Iohnston Island. Of
the agens discussed in detail in this document, only the agent mixture HT is in the U.S. chemical
weapons inve_ntory as fill for 6.2-in mortar and 105-mm artillery rounds. Agens L and HL were
produced during World War II and were stockpiled, but were disposed of by dumping at sea. There is
no record of the nitrogen mustards or Q having been stockpiled by the United States. The Russians
reportedly have a stockpile of L and HL that is slated for destruction.

In

1985, the U.S. Army was directed by law !o dispose of all unitary chemical munitions and
agent in bulk containers. Various disposal procedures have been studied for thepast several years. The
question of sites for disposal has also been under consideration. The cunent policy is that, due to the
hazards and restrictions associated with transportation of agent outside storage sites, disposal will be
carried out at each storage site. This decision dictates that a disposal facility be constructed at each site
fi.ef. 35).

6,2

CONSIDERATION OF DISPOSAL PROCEDURES

6.2.1

Disposal at Ocean Depths

This disposal method was employed prior to 1970 and was a simple disposal procedure because
the agent could be sunk intact, encased in a strong protective envelope. The procedure was complicated
by the need for long{istance transport and by the lack of information regarding the ultimate fate of the
agents and their impact on the ocean environment. The surfacing of mustard munitions dumped in the
Baltic Sea @ef. 23) presents a basis for concern regarding the hazard of such disposal. Disposal at sea
is now prohibited by the Marine Protection, Research, and Sanctuaries Act of 1972.

6.2.2

Chemical Decomposition

Investigation of methods of disposal of chemical agene.contained in chemical agent identification

kits included evaluation of chemical neutralization. Because of the low solubility of these agents in water
and water-based reactants, and because of production of products of decomposition that are potentially
toxic, chemical decomposition is not a favored disposal procedure.

In 1987, chemical treaty teams from various nations were invited by the Russians to visit and view
the chemical munition disposal facility developed by the Russians at Shikhany (Ref. 51). The system was
described as a thermochemical process. In the procedure, agetrt was drained ftom the munitions into the
neutralizer. Following neutralization of the agent, the products of neuualization were placed in the
combustion burner and exposed to a temperature of 1200oC. This procedure does not appear to offer
any advantage over direct incineration. The Shikhany disposd facility has since been inactivated because
of environmental concems.

47

DOCUMENT U'VCLASSIFIED IJPON REPRODUCTION JCP-L DPG

6.2.3

lncineration by Nuclear Detonation

Proposals have been made to place large quantities of chemical agent in a subterranean cavity
where a nuclear device could be detonated o produce temperarures that would dCIuoy the agent, the
containers, and the explosives in one operation. The unknowns and the known problems, such as the
nepd to transport agent to the site and the certainty of public opposition to the procedure, negate its
adoption.

6.2.4

Pyrolysis

Pyrolysis, accomplished by heating the agent to a high tempera$re in the absence of oxygen so
that the molecular strusture of the agent is altered to yield a nontoxic product, has been considered.
Uncertainty regarding the end products of pyrolysis lead to rejection of the procedure. The thermal
decomposition of mustard has been investigated. Complete decomposition of mustard in an atmosphere
of nitrogen was reported to be complete at 450oC, and the main products of decomposition were
hydrogen chloride, ethylene, ethylene dichloride, dithian, and 2:2'dichlorodiethyl disulfide; and at higher
temperatures, hydrogen sutfide and vinyl chloride (Ref. 37). These would be bxpected to occur with
pyrolysis of HT.

6.2.5

Combustion by Incineration

Past experience with incineration of mustard and GB has demonstrated the completeness of this
method of disposal. The oxidative combustion of mustard (BCES) is:

z(Clcfl); + 13 02+

8 COz + 2 SO,

+ 4 HCI +

6 H2O

The production of sulfur dioxide and hydrogen chloride necessitates their removal from the
discharge of combustion. Removal is accomplishable through the use of absorptive filters and scnrbbers
in the incinerator discharge train. There are incinerators at Tooele Army Depot [the Chemical Agent
Munitions Disposal System (eAMDS)l and at Johnston Atoll pohnston Atoll Chemical Agent Disposal
System (IACADS)]. The combustion of T in the HT mixture should yield end products similar to those
of agent H. Studies on incineration of agens in identification kits demonstrated effective incineration of
the nitrogen mustards, but problems noted with L included the ultimate disposal of the arsenic moiety
(Ref. 52, 53, 54).

6.2.6

Incinerator Design

The incinerator designed for disposal of ehemical agents is composed of four units:

a. Liquid

Incinerator

The liquid agent is drained from the munition or bulk container and is burned, along with any
liquid waste, in the liquid incinerator at 2700oF.

48

DOCUMENT UTVCLASSIFIED UPON REPRODUCTION JCP-\, DPG

b.

Metal Parts Furnace

The metd parts furnace decontaminates the munition casings and internal metal, whictr are heated
to a temperaure sufFrcient to destroy residual agent in or on the meal.

c.

Dqptivation Furnace

The deactivation furnace incinerates the explosive charges thathave been removed from chemical

munitions. The explosive materials are handled in a manner that accomplishes incineration without
explosive detonation. This treatment decomposes any residual chemical agent associated with ttre
explosive device.

d.

DunnaSq.Incinerator

The dunnage incinerator disposes of all solid, combustible waste.

Final approval for operation of disposal facilities in the continental U.S. has not been acquired
and is contingent on completion of testing and acceptancB of the Johruon Island facility.

49

DOCUMENT UAICTASSIFIED UPON REPROOUCTION JCP-\, DPG

APPENDIX

1.

Parker, Don

2.

Ward, Kyle,

A. REFERENCES

T. and Andrew C. Parker. Joint CB Technical Data Source Book, Volume V,

Blister, Blood, and Choking Agents; Part One: Agent H, Second Edition, March, 1993.

Jr.

The Ctlorinated Eftylanines - A New Tlpe of Vesicant. Iournal of the

American Chemical Society 57191*9L6, 1935.

3.

U.S. Arnii Field Manual 3-9. Potential Military Chemical/Biological e-gents and Compounds,
December 1990.

4.

Renshaw, Birdsey (Editor). Chemical Warfare Agents and Related Chemicd Problerns, Parts
II, and Parts IU-VI. National Deferue Research Committee, lVashington D.C, 1946, AD

I-

234270.

5.

U.S. Army Chemical Research, Dwelopment and Engineering Center. Aberdeen Proving
Ground, Maryland. Chemical Agent Data Sheets, Volume l. EA-SR-74001, AD8V28222,
December 1974.

6.

Field, John B, et d, Reversal of Nirogen Mustard Intoxication by Anti-Histamines. Proceedings of the Society of Experimentd Biology and Medicine. 115:106tr1ffi2,1964.

7.

Franke, Siegfried. Manual of Military Chemistry, Volume I - Chemistry of Chemical Warfare

Agens. East Berlin - 1976, Translation of the National Technicd Information Senrice,
AD849866.

E.

Gilman, Alfred, and Frederick S. Philips. The Biological Action and Therapartic Application
the F Chloroethyl Amimes urd Sulfides. Science 103:409415, 1946.

9.

Papirmeister, Bruno, et

al.

of

Molecular Basis for Mustard Induced Vesication. Fundamental and

Applied Toxicology, 5:S 13,1-5149, 1985.

10. Papirmeister, Bruno, Alan J. Feister, Sabrina I. Robinsorq and Robert D. Ford. Medical
Defense Against Mustard Gas: Toxic Mechanisms and Pharmacological Implications. CRC
Press, Boea Raton, Ann Arbor, Boston, 1991.

al. The Mechanism of Action of Nitrogen and Sulfur Mustard. Quarterly

Progress Report No. 1 to Chemicd Corps Procuremont Agency, Contract DA18-108ML3430, Iune 1952.

11. Wheeler, Glym P. et

12. Dorsey, J. Kwin, et

al.

Sensitization of Deoxyribonueleic Acid to Endonuclease in Adenine

Alkylation. Edgewood Arsend Technical Repot EATR 4650, Iune 1972, AD743M.
13. Greenwald, Blward S. Cancer Chemotherapy. Medical Examination hblishing Company,
Flushing, New York 1973.

A-l

DOCUMENT UNCTASS IFIED IJPON REPRODUCTION JCP.I, DPG

14. Anilkumar, T.V., et d. The Nature of Cytotoxic Drug-Induced Cell Death in Murine Intestinal
Crypts. British Iournal of Cancer 65:552-55E 1992.
15. Rhoads, C.P. Nitrogen Musards in the Treatsrent of Neoplastic Disease. Iournal of 0re
American Medical Association 13 I :656{5E, L946..

A., Iohn P. Bingham, and Robert L. Souhami. DNA Sequence Selectivity of

Quinine-M Alkyluionby Nirogen Mustard is Preserved in Intact Cells. Nucleic Acid
Research 20: 317 5-3l7t,

16. Hartley, Johtr

.1992.

17. Pechura, Constance M., and David P. Rall (Editors). Veterans at Risk; The Health Effects of
Mustard Gas and Lewisite. Nationd Academy Press, Washington,

D.C.

lE. U.S. Army Field Manual E-2E5. Treatment of Chemicd Agent Casualties
Military Chemicd Injuriec. FeDruary 1990.
19. Requena,

L.,

et

1993.
and Conventional

d. Chemical Warhre - Cutaneous Lesions from Mustard Gas. The Journd of

American Academy of Dermatology 19:529-536, 1988.

20. Drasch, Gustav, A al. Concenration of Mustard Gas [Bis(2{hloroahyl Sulfide] in ne Tissues
of a Victim of a Vesicant Exposure. Journal of Forensic Ssience 32(Q:1788-1793, 1987.
21. Freitag, Lutz, NosratFirusian, George Stamatis, and Dieer Greschuchna. The Role of Broncttoscopy in Pulmonary Complications Due to Mustard Gas Inhalation. Chest 100(fl:1a36
1441, tggl.

NiZ., Shahla Enshaeih, Montaza Meghdadi, and Mdihel Amindjavaheri. Skin

Manifestations of Mustard Gas. A Clinicd Study of 535 Patients Exposed to Mustard Gas.
Archives of Dermatology 128(6) :77 5-7 80, 1992.

22. Momeni,

23. Aasted, Annet, et al. Mustard Gas: Clinical, Toxicological, ud Mutagenic Aspects Based on
Modern Experienee. Annds of Plastic Surgery 19:330-335, 1987.
24. Fasth, Auli, and Bo Sorbo. Protective Effects of Thiosulfate and Metabolic Thiosulfate Precursors Against Toxicity of Niuogen Mustard (IINJ. Biochemicd Pharmacology 22: 1337-1351,
t913.
25. Field, J.8., A. Mireles, an<l E.C. Dolendo. Reversal of Nitrogen Mustard Intoxication by a
Serotonin Antagonist. Proceedings of the Society for Experimental Biology and Medicine

Itl:l-3,1962.
26. Bennen, George MacDonald, and Btith Muriel lVincop. Some Derivatives of Monothioahylene
Glycol. Journal of the Chemical Soci*y ll9:lt6G'lt&,1921.

A-2

DOCUMENT U'VCIASS I FIED UPON REPRO DUCTIO N JCP-|, DPG

27. Davies, J.S.H., and A.E. Oxford. Formation of Sulphonium Chlorides and Unsanrrated
Subsuncos by the Action of }Vater rnd Aquous Alcoholic Potash on p, p-Dichlorodiethyl
Sulphide. Journal of the C:hcrnical Sociay t2+216,1931.

28. Glasson, E.f., et al. New Organic Sulfur Veslcams, Part IV. l:2-Di-(2-chloroethylthio) Ether
and It Andogues. Journal of the Chemical Society (tondon) pp 4446.
Jan-June, 19E4.

29. Samuel, John B., Elwin C. Penski and lohn J. Callahan. Physicd Properties of Standard Agents
(U). AfrcSL-SP-83015, iune 1983. CONFIDENTTAL.
30. Koblin, Abraham. Field Sampling and Analysis of Agent Q. Interim Report{RLR 513, Army
Chemical Center, Maryland, Decernber, 1955, ADOM169.
31. \[oodward F.N. New Organic Sulphur Vesicants. Part I. 2:2-DF@+hloroethyltrio) die&yl
Ether. Journal of the Chemical Society (Iondon) Pages 35-38, January-June, 1984.
32. Lichterutadter, Manfred, and James D. Moneymalrer. Preparation and Proposed Semicontinuous
Process of Production of Agent Q. Formal Report CRLR 552, Army Chemical Center,
Maryland, April, 1955, ADO93393.
33. Reeves, A.M., et al. Process Development for Agent Q. Interim Report CRLR 490, Army
Chemical Center, Maryland, June 1955, AD 066179.
34. U.S. Army Service Forces Ofiice. Standudization of Persistent Agent, HT. Chief of the
Chemical Warfare Sewices, Item 1342. DPG Accession #526608.

35. U.S. National Research Council. Disposal of Chernical Munitions and Agents. National
Academy Press, Washington D.C, 1984.

s d. Problem Definition Shrdies of Potential Environmental Pollutants.

Physical, Chemical, Toxicological and Biological Properties of 16 Substances. U.S. Army
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Technical Report 7509 Decembet, 1975, ADA03U28. .

36. Rosenblatt, David H.,

II.

37. Tomlinson, Gretchen I., and Aryeh H. Samuel. Literanrre Survey of Physical and Chemical
Prcperties of Agents VX, GD, HD and HL. ARCSL-CR-t0051, fuly, 1980, AD8050375.

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Proving Ground. HD-L Eutectic Mixture Test. DPGR 128. February,

1953, AD0@523.

39. Peters, R.A., H.M. Sinclair, ud R.H.S. Thompson. An Andysis of the Inhibition of Pyruvate
Oxidation by Anenicals in Relation to the Enzyme Thmry of Vesication. Biochernical Journal
40:513-524, 1946.

A-3

DOCUMENT U/VCIASS IFIED UPON REPRODUCTION JCP-L DPG

\V. British Anti-Lewisite (BAL), The Classic Heavy Metal Antidote. Clinical
:215-222,
197 2.
5

40. Ochme, Frederick

Toxicology

41. Chinn, Kenneth

S.K.

Joint CB Technical Data Source Book (U), Volume XYI. Thickened

U.S. Army Dugway Proving Ground,

Chenical Warfare Agens (U). DPG-TR-81{03,

Dugwiy, Utah, ADC028236, Much 1982.

42. Boyle, Douglas G. A Selected Review of Thickonod Agent Programs, 1939 to 1976 (U).
DPGR-T-I3OA, U.S. Army Dugway Proving Ground, Dugway, Uteh, ADC0L4O52, October

1977. S1ECRET

M., and Marjorie F. Buckles. Mixtures of CV/ Agents for Use In Cold
Weather. CRLR 178 Army Chemical Center, Maryland, July, 1953, AD014882.

43. Zeffwt, Bernard

d.

44. Mengel, R. William, et

CB Technical Data Source Book, Volume
cation, and Warning. DPG/JOD-911V20, AD8158502, July 1991.
45. Goodman, Alan, and Kivah
June, 19t9,4D8134988.

4.

Detection, Identifi-

Y. Ong. M43Al Mustard Upgrade Evaluation. CRDEC-TN{06,

J. (Editor). Iane's NBC Protection Equipment,

Group, Inc. Alexandria, Virginia, 1991.

Gander, Terry

47. U.S. Army Field Manud

X[I,

34.

l99l-92.

Jane's Information

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Teams (DECAP CHUTE) Volume
Find Report DPG-FR-CI40A, June, 1977, ADC010850.

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49. Yurow, Harvey W., and George T. Davis. Decontamination and Disposal Methods for Chemical
Agents - A Literature Survey. ARCL-TR-81080. U.S. Army Armament Research and
Development Command, Aberdeen Proving Ground, MD, November 1982, AD 8069586.

Lowe, Harry N., and Don C. Lindsten. Removd of CBR Contaminants from Water. Military
Medicine l2l :330-335, 1975.
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Utatr. Visit to Shiktany, 1987. DPG/TA-

8E/025, August 1988, ADA199973.

52. Brooks, Marquerite E. Demilitarization of Identification Kits by Incineration. ARCSL-TR77921, U.S. Army Armament Research and Development Command, Aberdeen Proving
Ground, MD, June, 1977, AD B019-644L.

L.

Pilot-scale Incineration and Daection Interference Studies for the Disposal of

53. Duggan, Micael
Toxic Gas and War Gas Identification Sets. U.S. Army Armament Research and Development
Command, ARCSL-TT.-78048, May, 1979, ADB039046.

A4

DO C U M E NT U/VCLASS I F I ED IJ PO

N REP RO D U CT I O N J CP. I, DPG

54. Brooks, Marquerite 8., and Gmrge A. Parker. Incineration and $rolysis of Severd Agents and
Related Chemical Materials Contained in Identification SAs. ARCSL-TR-79040, U.S. Army
Armament Research and Development Cornmand, Aberdeen Proving Ground, MD, October,
1979 ADB042888L.

A-5

DOCUMENT UNCLASSIFIED UPON REPRODUCTION JCP-\, OPG

APPENDIX

DO49 DISTRIBUTION LIST

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