Mutagenicity of alpha-acetoxy derivatives of N-methyl-N-benzylnitrosamine and N,N-dibenzylnitrosamine in V79 cells: a comparison between methylating and benzylating mutagens.

The mutagenicity and cytotoxicity of N-methyl-N-(alpha-acetoxybenzyl) nitrosamine, N-benzyl-N-(acetoxymethyl) nitrosamine, N-benzyl-N-(alpha-acetoxybenzyl)-nitrosamine and related compounds were examined in V79 Chinese hamster cells. These three alpha-acetoxy nitrosamines were all mutagenic, the first one (a compound ultimately yielding a methylating species) being far more strongly mutagenic than the other two (compounds ultimately giving benzylating species). The alkylating or aralkylating activity of these compounds was determined by assessing their reactivity toward 4-(rho-nitrobenzyl) pyridine. The chemical reactivity-mutagenicity correlation among these alpha-acetoxy nitrosamines and related compounds is discussed in relation to the carcinogenicity of their mother compounds.