Characterization and mutagenicity of 1-nitrosotryptophol and 6-nitrotryptophol possible genotoxic substances associated with smoking and alcohol consumption.

ABSTRACT

Tryptophol (Typ) is a minor product of tryptophane metabolism in humans which is increased with alcohol consumption. Typ can react rapidly with nitrite at pH 3.0 to form 1-nitrosotryptophol (NO-Typ) in high yield. This product is also formed in various organic solvents by the reaction of NO/NO2 mixtures with Typ. Under similar conditions, NO2 in the absence of NO will react with Typ to form 6-nitrotryptophol (NO2-Typ). Both products, NO-Typ and NO2-Typ, are mutagenic when tested in the absence of rat liver microsomes with a variety of Salmonella typhimurium tester strains.