The biochemistry of aromatic amines. 2-Formamido-1-naphthyl hydrogen sulphate, a metabolite of 2-naphthylamine

Abstract

2-Formamido-l-naphthyl hydrogen sulphate is excreted by dogs and rats dosed with 2-naphthylamine or with 2-amino-1-naphthyl hydrogen sulphate and was isolated from dog urine. 2-Formamido-1-naphthol, naphtho[2,l-d]oxazole and N-formyl-2-naphthylhydroxylamine are excreted as (2-formamido-1-naphthyl glucosid) uronic acid. 2-Formamidonaphthalene is converted into conjugates of 2-amino-6-naphthol and 2-amino-8-naphthol, but 2-methylaminonaphthalene is excreted as 2-amino-l-naphthyl hydrogen sulphate and its N-methyl and N-formyl derivatives and (2-amino-l-naphthyl glucoside) uronic acid. 2-Methylamino-1- naphthyl hydrogen sulphate is converted into 2-formamido-1-naphthyl hydrogen sulphate and 2-amino-l-naphthyl hydrogen sulphate on charcoal. 2-Amino-1-napthyl hydrogen sulphate and formaldehyde react on charcoal to yield 2-methylamino- and 2-formamido-1-naphthyl hydrogen sulphate. 2-Formamido-l-naphthol, 2-formamido-1-naphthyl hydrogen sulphate, N-formyl-2-naphthylhydroxylamine and N-formyl-2-naphthylhydroxyl-amine-O-sulphonic acid were synthesized.