2-Chlorobenzylmercapturic acid, a metabolite of the riot control agent 2-chlorobenzylidene malononitrile (CS) in the rat

Abstract

Adult male Wistar rats administered i.p. with 2-chlorobenzylidene malononitrile (CS) excreted one mercapturic acid in urine. The amount of mercapturic acid determined gaschromatographically was about 4% of the dose (0.07 mmol/kg, n = 12). The structure of the mercapturic acid methylester was identified by t.l.c. and confirmed by synthesis and mass-spectrography. The acid appeared to be 2-chlorobenzylmercapturic acid [N-acetyl-S-(2-chlorobenzyl)-L-cysteine]. CS and some of its metabolites were also tested in the Ames Salmonella/microsome assay. Both mutagenic and toxic effects were measured with strain TA 100 as the indicator organism. No mutagenic effects were found with any of the tested substances. At dosages of CS, higher than 1,000 micrograms/plate a bacteriotoxicity was revealed.

Riot control agents: pharmacology, toxicology, biochemistry and chemistry

“…As reported by von Daniken et al, 285 CS was positive for mutagenicity in the Ames assay; however, subsequent findings by Zeiger et al 286 indicated questionable genotoxicity for S. typhimurium. Findings by Rietveld et al 287 and Wild et al 288 indicated that CS was non-mutagenic for S. typhimurium. Mutagenicity studies by Meshram et al 289 using the Ames assay also demonstrated that CS did not induce a mutagenic response in the presence or absence of S9 mix.…”

The Respiratory Toxicity of Chemical Warfare Agents

“…However, it is believed that in the case of inhalation exposure, the amount of formed thiocyanide may have little if any role in human toxicity (Ballantyne, 2006). administration of CS to rats results in its excretion in the urine as mercapturic acid (Rietveld et al, 1983). CS is an SN 2 -alkylating agent with active halogens, which react with nucleophilic sites.…”

Military Smokes and Obscurants Fate and Effects: A Literature Review Relative to Threatened and Endangered Species

“…There are several inhalation studies available (Ballantine and Callaway 1972, Ballantine et al 1974, Ballantine and Swanston 1978 and one study in laboratory rats (Rietveld et al 1983) using i.p. injection.…”