Characterization and mutagenicity of 1-nitrosotryptophol and 6-nitrotryptophol possible genotoxic substances associated with smoking and alcohol consumption.
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.
Tanaka
K
K
Meiji College of Pharmacy, Tokyo, Japan.
McConnell
B
B
Niemczura
W P
WP
Mower
H F
HF
D000428:Alcohol Drinking; D007211:Indoles / Q000138:chemical synthesis*; D009682:Magnetic Resonance Spectroscopy; D009152:Mutagenicity Tests; D012486:Salmonella typhimurium / Q000187:drug effects; D012907:Smoking; D013056:Spectrophotometry, Ultraviolet
D007211:Indoles; C058724:6-nitrotryptophol; C058723:1-nitrosotryptophol