Arsines Lewisite

Chemical Agent L (Lewisite) Agent L is a blister agent, Dichloro 2-chlorovinyldichloro-arsine, (CAS 541-25-3) with a chemical formula of C2H2AsC13. 

DETAILS - Arsine is a common by-product of many chemical industries. The Lewisite gas used in WW1 was a form of arsine. The weapons section has a gas grenade which generates arsine. Arsine is at it-s best when used in enclosed areas in heavy concentration. Death from this type of exposure is remarkably quick as the gas shuts down the central nervous system in a matter of seconds. 

Other organoarsenicals, most notably lewisite (dichloro[2-chlorovinyl]arsine), were developed in the early twentieth century as chemical warfare agents. Arsenic trioxide was reintroduced into the United States Pharmacopeia in 2000 as an orphan drug for the treatment of relapsed acute promyelocytic leukemia and is finding expanded use in experimental cancer treatment protocols (see Chapter 54). Melarsoprol, another trivalent arsenical, is used in the treatment of advanced African trypanosomiasis (see Chapter 52). 

Arsine Derivotives,Organic Many arsine derivs were proposed as CWA s. More than 60 of such derivs are listed by Wachtel (Ref, pp 189-92). The most known of these compds is Lewisite or Ml, which is fi-chlara-vinyldichlorodrsine, C1 CH CH AsCla, first... 

Arsine derivs used by the Germans were not as effective as Lewisite. They included a) Dic ,US designation EDt ethyldicbloroarsine... 

Arsine and derivs 1 A491 Adamsite 1 A491 arsine derivs, organic 1 A491 Clark I and I11 A491 Dick 1 A491 Lewisite 1 A491... 

Arsine Derivatives,Organic. Many arsine derivs were proposed as CWA s. More than 60 of such derivs are listed by Wachtel (Ref, pp 189-92). The most known of these compds is Lewisite or MI, which is f -cbloro-vinyldichloroarsine, C1-CH CH- AsC12, first isolated in 1917 by Dr W. Lee Lewis and developed as a war gas by the US Chemical Warfare Service (Ref, pp 202-6). Another important arsine CWA is Adamsite (Brit) (designated in the US as DM) or diphenylamine-chloroarsine ... 

Arsine derivs used by the Germans were not as effective as Lewisite. They included a) Dick,US designation ED, ethyldichloroOrsine C,H, -AsCl, (Ref, p 194) b)C/ar / (US designation DA) biphenylchloroarsine,... 

Lewisite [dichloro(2-chlorovinyl)arsine] is an organic arsenical known for its vesicant properties (Rosenblatt et al., 1975). It has a molecular weight of 207.32, vapor pressure of 0.58 mm HG at 25°C, a liquid density of 1,89 g/cm at 25°C, freezing point of -18°C, boiling point of 190°C, and is negligibly soluble in water (DA, 1974). The chemical structure of lewisite is shown below. Lewisite may occur as a trans-isomer and as a cis-isomer. In aqueous solutions, the cis-isomer undergoes photoconversion to the trans-isomer (Clark, 1989). hi the presence of moisture, lewisite is rapidly converted to the more stable but highly toxic lewisite oxide (2-chlorovinylarsenous acid) (Cameron et al., 1946). 

Lewisite, dichloro(2-dichlorovinyl)arsine is a chemical that contains arsenic, which though a liquid is sufficiently volatile to be dispersed among enemy troops. The arsenic atom in the lewisite reacts with proteins and causes terrible blisters on the skin and damage to the eyes and lungs if inhaled. Fortunately, an antidote was devised as a result of the work of the British biochemist Rudolf Peters. The antidote was appropriately named British anti-lewisite (dimercaprol), and abbreviated to BAL. 

Lewisite [L or L-1 dichloro(2-chlorovinyl) arsine] is an arsenical vesicant developed early in the 20th century. Lewisite occurs as cis- and tranx-isomers the typical ratio being 10 90. Several impiuities including 6w(2-chlorovinyl) chloroarsine (L-2) and tnY(2-chlorovinyl)arsine (L-3) are typically present. The chemical and physical properties of the cis- and tranj-isomers are similar. 

Lewisite (L) Synonyms 2-chlorovinyldichloroarsine (2-chlorovinyl)arsenous dichloride beta-chlorovinyldichloroarsine dichloro(2-chlorovinyl) arsine chlorovinylarsine dichloride EA 1034... 

Lewisite in soil may rapidly volatilize or may be converted to lewisite oxide due to moisture in the soil (Rosenblatt et al, 1975). The low water solubility suggests intermediate persistence in moist soil (Watson and Griffin, 1992). Both lewisite and lewisite oxide may be slowly oxidized to 2-chlorovinylarsonic acid (Rosenblatt et al, 1975). Possible pathways of microbial degradation in soil include epoxidation of the C=C bond and reductive deha-logenation and dehydrohalogenation (Morrill et al, 1985). Due to the epoxy bond and arsine group, toxic metabolites may result. Additionally, residual hydrolysis may result in arsenic compounds. Lewisite is not likely to bioaccumulate. However, the arsenic degradation products may bioaccumulate (Rosenblatt et al, 1975). 

SYNS (2-CHLOROETHENYL) ARSONOUS DICHLORIDE P-CHLOROVINYLBICHLOROARSINE 2-CHLOROVINYLDICHLOROARSINE (2-CHLOROVINYL)DICHLOROARSINE DICHLORO(2-CHLOROVINYL)ARSINE n LE STSITE n LEWISITE (ARSENIC COMPOUND)... 

All the war gases have not been included in Table XII, but only the most important. Those not included may be easily classified into their proper groups. Acrolein, for instance, in the aldehyde group, lewisite and diphenyl cyanoarsine in that of the arsines, methyl cyanoformate and ttiethyl chloroformate in that of the esters. 

In acute exposure prompt medical attention is critical. The victim should be immediately removed to fresh air and away from the source of exposure. Oxygen should be provided if there is a respiratory distress. Initial therapy should be directed at stopping the ongoing hemolysis by performing exchange transfusion. Currently there is no other treatment to decrease arsine hemolysis however, studies in vitro have shown that some dithiol chelators (meso-2,3-dimercaptosuccinic acid, DMSA 2,3-dimercapto-l-propanesulfonic acid, DMPS and 2,3-butanedithiol) are effective (see Further Reading). This should be followed by aims to restore renal function or compensate for lost renal function (hemodialysis). This process does not remove any formed arsenic from the exposed body. Administration of dimercaprol (British Anti-Lewisite, BAL) has no effect on arsine hemolysis, but it lowers blood arsenic levels resulting from arsine exposure. The use of chelators must be... 

Chemical Abstracts Service Registry Numbers CAS 541-25-3 (Lewisite 1 2-chlorovinyldichlo-roarsine) CAS 40334-69-8 (Lewisite 2 (2-chlorovinyl)chloroarsine) CAS 40334-70-1 (Lewisite 3 Tris(2-chlorovinyl)arsine)... 

P-chlorovinyldichloroarsine. (l-chloro-2-di-chloroarsinoethane dichloro[2-chlorovinyl] arsine chlorovinylarsinedichloride Lewisite). Two isomers, probably cis and trans, are known. CICIfCIIAsCL... 

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