The biochemistry of aromatic amines. 5. 2-Acetamido-6-hydroxy-5-naphthyl hydrogen sulphate and other metabolites of 2-naphthylamine and 2-acetamidonaphthalene

Abstract

The isolation of 2-acetamido-6-hydroxy-5-naphthyl-hydrogen sulfate from the urine of rabbits injected with 2-acetamidonaphthalene is described. The compound was detected in the urine of rabbits and rats injected with 2-naphthylamine. The compound was synthesized by the persulfate oxidation of 2-nitro-6-naphthol followed by reduction and acetylation with thioacetic acid. The urine of rats and rabbits injected with 2-naphthylamine was examined by paper chromatography. 2-Naphthylamine, 2-acetamidonaphthalene, 2-acetamido-6-naphthol, 2-amino-l-naphthyl hydrogen sulfate and a compound which is probably 2-acetamido-5,6-dihydro-5,6-dihydroxynaphthalene were detected. Rat urine sometimes contained 2-amino-6-naphthol and its hydrogen sulfate. The injection of 2-acetamidonaphthalene gave the same products except that 2-naphthylamine was not detected in rabbit urine and 2-amino-6-naphthol and its hydrogen sulfate were not detected in rat urine. 2-Amino-l-naphthol, 2-acetamido-l-naphthol and 2-acetamido-l-naphthyl hydrogen sulfate were not detected as metabolites of 2-naphthylamine or 2-acetamidonaphthalene in the urine of rats or rabbits. The oxidation of 2-acetamidonaphthalene by an ascorbic acid-ferrous sulfate-oxygen system yields a compound which is probably 2 -acetamido-5,6-dihydroxynaphthalene.