The biochemistry of aromatic amines. 2. The conversion of arylamines into arylsulphamic acids and arylamine-N-glucosiduronic acids

Abstract

The urine of rabbits dosed with 2-naphthylaminc contains 2 acid-labile derivatives of 2-naphthylamine 2-naphthylsulfamic acid and 2-naphthylamine N-glucosiduronic acid. Sodium 2-naphthylsulfa-mate, which readily yields 2-naphthylamine in cold acid solution, was isolated from the urine of rabbits and detected by paper chromato-graphy in the urine of rats but not of hamsters or guinea pigs dosed with 2-naphthylamine. Phenylsulfamic acid was detected in urine of rabbits but not of rats dosed with aniline. 1-Naphthylsulfamic acid was detected in the urine of rabbits but not of rats dosed with 1-naphthylamine. 4-Diphenylylsulfamic acid did not appear to be formed from 4-aminodiphenyl by either rats or rabbits. Sodium 2-naphthylamine N-glucosiduronate was isolated from urine of rabbits dosed with 2-naphthylamine and detected in urine of rats dosed with the amino. The 2-naphthylamine-N-glucosiduronate was shown by infrared absorption to have a structure similar to 2-naphthylamine N-glucoside. Urine of rats and rabbits dosed with 2-naphthylamine contains an acid-labile derivative of 2-amino-1-naphthylsulfuric acid. This compound is not the sulfuric ester of 1-hydroxy-2-naphthyl-sulfamic acid, which was synthesized, but is 2- amino-1-naphthylsulfuric acid N-glucosidurone acid.