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.