Solvolysis of N-nitroso-N-(1-acetoxyalkyl)alkylamines in phosphate buffer: characterization and mutagenicity of N-nitroso-N-(1-phosphonooxyalkyl)alkylamines.

The kinetics of solvolysis of some α-acetoxy nitrosamines in phosphate buffer solution was investigated and their mutagenic products were identified. N-Nitroso-N-(1-acetoxyalkyl)alkylamines were decomposed in two ways in aqueous phosphate buffer solution : O-acyl fission yielded α-hydroxy nitrosamines which were decomposed into aldehydes and alcohols, while O-alkyl fission gave a resonance hybrid of α-N-nitroso carbonium and iminium ions which, when trapped with phosphate, afforded N-nitroso-N-(1-phosphonooxyalkyl)alkylamines. They were stable in neutral and alkaline aqueous solutions, and were mutagenic in Salmonella typhimurium TA1535 and Escherichia coli WP2 and WP2 hcr-.