Metabolism of polycyclic compounds. 12. An acid-labile precursor of 1-naphthylmercapturic acid and naphthol: an N-acetyl-S- (1:2-dihydrohydroxynaphthyl)-l-cysteine

Publisher Website
Google Scholar
Abstract
A substance was detected in and isolated from the urine of rabbits dosed with naphthalene which on acidification with mineral acid gives rise to 1-naphthylmercapturic acid and 1- and 2-naphthol. From a consideration of the acid decomposition products and the fact that it gives 1-naphthylmercapturic acid and 2-naphthol on treatment with alkali it is suggested that the compound is N-acetyl-S-(l:2-dihydro-2-hydroxynaphthyl)-L-cysteine. A number of physical properties of the compound are recorded. The compound was not produced when rabbits were injected with 1-and 2-naphthol, dl-trans-l:2-dihydro-l:2-dihydroxynaphthalene or S-1-naphthyl-L-cysteine. Traces were produced with l:2-dihydro-naphthalene. Rats, mice, hamsters, guinea pigs and man all excreted the precursor after treatment with naphthalene. Possible modes of formation of the precursor in the body are discussed.