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  • Title: Structural elucidation of a mutagenic metabolite of 3-amino-1-methyl-5H-pyrido[4,3-b]indole.
    Author: Yamazoe Y, Ishii K, Kamataki T, Kato R.
    Journal: Drug Metab Dispos; 1981; 9(3):292-6. PubMed ID: 6113943.
    Abstract:
    Metabolic activation of a tryptophan pyrolysate, 3-amino-1-methyl-5H-pyrido[4,3-b]indole (Trp-P-2) by liver microsomes was studied. Trp-P-2 was converted to at least four metabolites (M-1 to M-4), which were separable by HPLC or TLC. Among them, the major metabolite (M-3) was extremely mutagenic to Salmonella typhimurium TA 98 in the absence of activating enzymes and the activity accounted for almost all mutagenic effects of Trp-P-2. Metabolite M-3 was identified as 3-hydroxyamino-1-methyl-5H-pyrido[4,3-b]indole by mass spectrometry and by conversion to the 4-chloro derivative of Trp-P-2 by treatment with hydrochloric acid. The latter compound was identified by NMR and mass spectrometry.
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