Formation of mercapturic acids. 5. Metabolism of some halogenoparaffins and nitroparaffins

Abstract

The metabolic formation of a purely aliphatic mercapturic acid was first recorded by Thomson, Maw & Young (1958) reported the excretion of ethylmercapturic acid by rats dosed with bromoethane, and Grenby & Young (1959, 1960) showed that n-propyl- mercapturic acid was excreted by rats, rabbits, guinea pigs and mice to which 1-bromo-or 1-iodo- propane had been administered. Bray & James (1958) obtained evidence suggesting that 1-bromobutane, -pentane, -hexane, -heptane and -octane, and 1-nitro-ethane and -propane, formed mer- capturic acids in the rabbit, and Barnes, James & Wood (1959) showed that a similar reaction occurred with 1-nitrobutane in the rabbit and rat. The evidence was the increased concentration of thiol compounds (as measured by the intensity of the colour given with sodium nitroprusside) ob- served in the alkali-hydrolysed urines from animals dosed with the bromoalkanes and the chromatographic detection of the mercapturic acids. It was recognized that the nitroprusside reaction was not specific for mercapturic acids and fractionation of the 'apparent mercapturic acid' into ether-soluble (mercapturic acid) and ether- insoluble (sulphur-containing material that was not mercapturic acid) was reported by Bray & James (1960). In the present paper a specific method for the estimation of the aliphatic mer- capturic acids is described, and the isolation of some aliphatic mercapturic acids is reported. A preliminary account has been given MATERIALS