AbstractN‐nitro [14C]methylamine was synthesized by the alkaline cleavage of N‐nitro[methyl‐14C] methylurethane obtained by nitration of [N ‐ methyl‐14C] methylurethane. N‐nitro[N‐methyl‐14C]dimethylamine could be obtained by methylation of monomethylnitramine with [14C] diazomethane.

The metabolic conversion of N-nitrodimethylamine and of N-nitrosodimethylamine was compared in vitro. The biochemical properties of the two compounds were nearly identical; however, the biological activities (carcinogenicity, mutagenicity and toxicity) of the nitramine are many times less potent. N-Nitrodimethylamine was found to be mutagenic to Salmonella typhimurium TA100 when applied at above 200 mumol/plate with metabolic activation. Its suggested metabolite, N-nitromethylamine, was not mutagenic, N-Nitromethylhydroxymethylamine, N-nitromethylacetoxymethylamine and formaldehyde were mutagenic only to S. typhimurium TA100 at low concentrations and toxic above 2 mumol/ plate. The evidence suggests that formaldehyde is the intermediate responsible for the mutagenicity of the nitramine derivatives and of the parent compound, N-nitrodimethylamine.