Add time:08/24/2019         Source:sciencedirect.com

Earlier observations on the reaction of some 2-naphthylamine metabolites with thiols have been extended. 2-Amino-1-naphthyl sulphate, bis-(2-amino-1-naphthyl)-hydrogen phosphate and 2-amino-1-naphthyl glucosiduronic acid arylate N-acetylcysteine and glutathione at pH 7.0 at 37° to give the corresponding S-(2-amino-1-naphthyl) derivatives. These metabolites may therefore not be inert excretion products. N-Formyl, N-acetyl and N-sulpho derivatives do not appear to react. 2-Methylamino-and 2-dimethylamino-1-naphthyl sulphates and 3-methyl-2-amino-1-naphthyl sulphate react with the thiols. Bis-(2-nitro-1-naphthyl)-hydrogen phosphate reacts to give 2-nitro- and 2-amino-1-naphthyl derivatives. No reaction was observed between some other o-aminoaryl sulphates and thiols. The reaction is discussed in relation to the metabolism and carcinogenicity of aromatic amines.

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