Sulfur mustards alkylating effects

Field First Aid Decontaminate At Once for All Exposed Victims Although sulfur mustards cause cellular changes within minutes of contact, the onset of pain and other clinical effects are delayed for one to twenty-four hours. Sulfur mustards are alkylating agents that may cause bone marrow suppression and neurologic and gastrointestinal toxicity. However, the biochemical mechanisms of action are not clearly understood by anyone. The death rate from exposure to sulfur mustard during World War I was 2-3 percent,... 

In the review by Papirmeister et al. (1991), it was noted that sulfur mustard-induced cytotoxicity is dose dependent and that DNA appeared to be more sensitive to mustard-induced alkylation than are other cellular constituents. The low-dose effects of sulfur mustard are characterized by gen-otoxicity and inhibition of mitosis. The loss of cellular reproduction may be due to bifunctional alkylation that ultimately prevents normal DNA replication. It was hypothesized that monofunctional DNA damage might be responsible for low-dose mutagenic and possibly carcinogenic effects. 

Meier, H.L., Johnson, J.B. (1992). The determination and prevention of cytotoxic effects induced in human lymphocytes by the alkylating agent 2,2 -dichlorodiethyl sulfide (sulfur mustard, HD). Toxicol. Appl. Pharmacol. 113 234-9. 

First, sulfur mustard, a vesicant warfare agent, was produced and used in World War I. Mustards alkylate a wide range of biologically important molecules producing c)dostatic, mutagenic, and cytotoxic effects. In 1936, just before the start of World War II, tabun was synthesized and then produced as the first nerve CWA. Nerve agents inhibit acetylcholinesterase (AChE) throughout... 

The numerous straightforward examples of internal displacement reactions leading to isolable cyclic products will not be discussed here, but only, for the most part, those ionization reactions in which a cyclic intermediate or transition state is deduced from the rearranged structure of the product. A well-known example is mustard gas and other alkyl chlorides with sulfur on the /3-carbon atom. Although mustard gas is a primary and saturated alkyl chloride, its behavior is like that of a typical tertiary alkyl chloride. It reacts so fast by a first order ionization that the rate of the usual second order displacement reaction of primary alkyl halides is not measureable. Only the ultimate product, not the rate, is determined by the added reagent.228 Since the effect of the sulfur is too large to be explicable in terms of a carbon sulfur dipole or similar explanation, a cyclic sulfonium ion has been proposed as an... 

Participation of sulfides through three-membered rings was used to gruesome effect in ck the development of mustard gas during the Second World War. Mustard gas itself owes its toxicity to the neighbouring group participation of sulfur, which accelerates its alkylation reactions. 

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