Formation, deoxygenation and mutagenicity of alpha-hydroperoxydialkylnitrosamines.
N-Nitroso-N-alkyl-alpha-hydroperoxyalkylamines were prepared either by treatment of N-nitroso-N-alkyl-alpha-acetoxyalkylamines with hydrogen peroxide in acetic acid or by oxygenation of lithiated N-nitrosodialkylamines with oxygen. They were strongly mutagenic towards S. typhimurium TA1535 and E. coli WP2 strains without metabolic activation. Treatment of the alpha-hydroperoxy compounds with deoxygenating agents, such as sodium bisulfite, gave the alpha-hydroxynitrosamine, which could be isolated in aprotic solvents and characterized. The alpha-hydroperoxy compounds can possibly be formed from N-nitrosodialkylamines by biochemical and environmental routes and can serve as precursors for the alpha-hydroxynitrosamines.
D055598:Chemical Phenomena; D002621:Chemistry; D004926:Escherichia coli / Q000187:drug effects; D009152:Mutagenicity Tests; D009153:Mutagens; D009602:Nitrosamines / Q000138:chemical synthesis / Q000494:pharmacology; D010084:Oxidation-Reduction; D010545:Peroxides / Q000138:chemical synthesis / Q000494:pharmacology; D012486:Salmonella typhimurium / Q000187:drug effects; D013329:Structure-Activity Relationship
D009153:Mutagens; D009602:Nitrosamines; D010545:Peroxides