ETHCHLORVYNOL: POTENTIAL OF METABOLITES FOR ADVERSE EFFECTS IN MAN

Identification of low levels of l-chloro-3-ethynylpent-1-en-3,4-diol (VII) a metabolite of the sedative-hypnotic, ethchlorvynol (I), has been achieved by GC/MS/CS analysis of biological specimens derived from victims of fatal and nonfatal poisonings. The assigned structure has been confirmed by synthesis which proceeds to VII via 1-chloro-3,4-epoxy-1-pentene (VI), the presumed metabolic precursor of VII. The activity of VI as both a mutagenic and cytotoxic agent suggests that I can be the origin of adverse reactions in man.