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

Exposure to 2-naphthylamine is known to cause cancer of the bladder, but not of any other organ in man. For this and other reasons the carcinogenic effect is thought to be exerted through some meta- bolite excreted in the urine. The metabolism of this and other aromatic amines has therefore been intensively studied, and a list of the known metabolites of 2-naphthylamine is given in Table Acetamido-6-hydroxy-5-naphthyl hydrogen sul- phate (described in the present paper) has been isolated as a metabolite of 2-acetamidonaphthalene and detected as a metabolite of 2-naphthylamine. EXPERIMENTAL Methods Animal&. Animals were kept in metabolism cages and the urine was collected daily. Rabbits (average wt. 2 kg.) were fed on cabbage, bran and water, and rats on rat cake, bread and water. Rabbits were injected intraperitoneally with 0-5 g. of 2-naphthylamine or 0-5 g. of 2-acetamido- * Part 4: Boyland & Manson (1957).