Detail of "581-97-5"

Reference

The metabolic activation of 2-naphthylamine to mutagens in the Ames test

The metabolic activation of 2-naphthylamine to mutagens in the Ames test. Tong, S.; Smith, J.; Manson, D.; Gorrod, J. W.; Ioannides, C. (Biochem. Dep., Univ. Surrey, Guildford/Surrey GU2 5XH, UK). Anticancer Res., 6(5), 1107-12 (English) 1986. CODEN: ANTRD4. ISSN: 0250-7005. DOCUMENT TYPE: Journal CA Section: 4 (Toxicology) The mutagenicity of 2-naphthylamine [91-59-8] and its major metabolites in the Ames test was detd. in the absence and presence of activation systems derived from rats and hamsters. In the absence of an activation system only N-hydroxy-2-naphthylamine (I) [613-47-8] and 2-nitrosonaphthalene [6610-08-8] were mutagenic. In the presence of activation systems derived from control and 3-methylcholanthrene-treated hamsters and Arochlor 1254-treated rats only 2-naphthylamine exhibited a mutagenic response whereas its hydroxy derivs. and 2-acetamidonaphthalene [581-97-5] were devoid of mutagenicity. Pretreatment of rats with 3-methylcholanthrene or Arochlor 1254 enhanced the mutagenicity of 2-naphthylamine while treatments with phenobarbitone, safrole, and clofibrate had no significant effect. In the hamster treatment with only 3-methylcholanthrene increased the mutagenicity of 2-naphthylamine. Thus, the metabolic activation of 2-naphthylamine proceeds via N-hydroxylation which is preferentially catalyzed by the 3-methylcholanthrene inducible forms of cytochrome P 450, whereas ring hydroxylation appears to be a deactivation pathway.

Metabolism of 2-napthylamine and benzidine by rat and human bladder organ cultures

Metabolism of 2-napthylamine and benzidine by rat and human bladder organ cultures. Moore, Brian P.; Potter, Philip M.; Hicks, R. Marian (Med. Sch., Middlesex Hosp., London W1P 7LD, UK). Carcinogenesis (London), 5(7), 949-54 (English) 1984. CODEN: CRNGDP. ISSN: 0143-3334. DOCUMENT TYPE: Journal CA Section: 4 (Toxicology) The metab. of benzidine [92-87-5] and 2-naphthylamine (I) [91-59-8], which are carcinogenic for the human, was investigated in human and rat bladder organ cultures. There was little oxidative metab. of either carcinogen in either species. In particular, N-hydroxy-2-naphthylamine, a proximate carcinogen of I, could not be detected. In contrast, large amts. of the acetylated metabolites, N-acetylbenzidine [3366-61-8], N,N-diacetylbenzidine [85985-50-8], and N-acetyl-2-naphthylamine [581-97-5] were formed in the rat and human bladder cultures. Thus, metab. of these carcinogens in situ in the bladder is unlikely to contribute to their carcinogenic effect but instead may have a pos. protective role.