The Carcinogenic and Mutagenic Properties of TV-Hydroxy-aminonaphthalenes1'2

Af-Hydroxy-1-aminonaphthalene (JV-hydroxy-1-AN), N-hydroxy-2-aminonaphthalene (N-hydroxy-2-AN), 1-aminonaphthalene (1-AN), 2-aminonaphthalene (2-AN), and 2-amino1,4-naphthoquinone were repeatedly injected i.p. into rats at a dose of 5 mg/100 gm. Lower doses of 2-amino-l-naphthol (0.15 mg/100 gm), and of #-hydroxy-aniline (1.3 mg/100 gm) were also given i.p. ./V-Hydroxy-1-AN was a more potent carcinogen than Af-hydroxy-2-AN ; the other compounds were not notably carcinogenic. The mutagenicity of W-hydroxy-1AN and N-hydroxy-2-AX was demonstrated in several mu tants of Escherichia coli. The greater carcinogenicity of Nhydroxy-1-AN, a metabolite of 1-AN, as compared with W-hydroxy-2-AN suggests that Af-hydroxylation is by itself an insufficient metabolic step in the formation of a proximate carcinogen.