The Metabolic Formation of Mercapturic Acids from Allyl Halides

Abstract

1. Male rats have been dosed subcutaneously with allyl chloride, bromide and iodide, and with S-allylglutathione and S-allyl-L-cysteine. 2. Allylmercapturic acid has been isolated from the urine of rats dosed with allyl chloride and S-allyl-L-cysteine and has been shown to be a metabolite of the other allyl compounds. The sulphoxide of allylmercapturic acid has been detected in the urine of all the animals which excreted allylmercapturic acid. 3. 3-Hydroxypropylmercapturic acid has been identified by gas-liquid chromatography as a metabolite of allyl chloride and evidence has been obtained for its presence in the urine of rats dosed with allyl bromide and iodide. S-Allylglutathione and S-allyl-L-cysteine have been detected in the bile of a rat dosed with allyl chloride. 4. The mechanism of the biosynthesis of mercapturic acids from allyl halides is discussed.