The biochemistry of aromatic amines. 2-Formamido-1-naphthyl hydrogen sulphate, a metabolite of 2-naphthylamine |
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Authors: | E Boyland and D Manson |
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Institution: | Chester Beatty Research Institute (Institute of Cancer Research: Royal Cancer Hospital), Fulham Road, London, S.W. 3 |
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Abstract: | 1. 2-Formamido-1-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. 2-Formamido-1-naphthol, naphtho2,1-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-1-naphthyl hydrogen sulphate and its N-methyl and N-formyl derivatives and (2-amino-1-naphthyl glucosid)uronic acid. 3. 2-Methylamino-1-naphthyl hydrogen sulphate is converted into 2-formamido-1-naphthyl hydrogen sulphate and 2-amino-1-naphthyl hydrogen sulphate on charcoal. 2-Amino-1-naphthyl hydrogen sulphate and formaldehyde react on charcoal to yield 2-methylamino- and 2-formamido-1-naphthyl hydrogen sulphate. 4. 2-Formamido-1-naphthol, 2-formamido-1-naphthyl hydrogen sulphate, N-formyl-2-naphthylhydroxylamine and N-formyl-2-naphthylhydroxylamine-O-sulphonic acid were synthesized. |
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