Biochemical and biological properties of prospective N-nitrodialkylamine metabolites and their derivatives

IARC Sci Publ. 1984:(57):491-7.

Abstract

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.

Publication types

  • Comparative Study
  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Biotransformation
  • Dimethylamines / metabolism*
  • Dimethylamines / toxicity
  • Dimethylnitrosamine / metabolism*
  • Dimethylnitrosamine / toxicity
  • In Vitro Techniques
  • Male
  • Microsomes, Liver / metabolism*
  • Mutagenicity Tests
  • Mutagens / metabolism*
  • Rats
  • Rats, Inbred Strains
  • Salmonella typhimurium / drug effects
  • Salmonella typhimurium / genetics

Substances

  • Dimethylamines
  • Mutagens
  • dimethylnitramine
  • Dimethylnitrosamine