Synthesis and properties of vinyl carbamate epoxide, a possible ultimate electrophilic and carcinogenic metabolite of vinyl carbamate and ethyl carbamate

Biochem Biophys Res Commun. 1990 Jun 29;169(3):1094-8. doi: 10.1016/0006-291x(90)92007-m.

Abstract

Vinyl carbamate reacted with dimethyldioxirane in dry acetone to give a high yield of pure crystalline vinyl carbamate epoxide. This epoxide was characterized by its NMR and MS spectra and elementary analysis. It is unstable at room temperature and has a half-life in water solution of approximately 32 minutes. It reacts with adenosine to form 1,N6-ethenoadenosine and more of this etheno nucleoside was found in hydrolysates of hepatic RNA of male mice injected i.p. with the epoxide than with vinyl carbamate. Tests with Salmonella typhimurium TA1535 showed that this epoxide is a strong direct mutagen. It is also more toxic in the mouse than vinyl carbamate. Studies on the carcinogenicity of this epoxide are in progress.

Publication types

  • Research Support, U.S. Gov't, P.H.S.

MeSH terms

  • Animals
  • Chemical Phenomena
  • Chemistry
  • Crystallography
  • Epoxy Compounds* / chemical synthesis
  • Epoxy Compounds* / toxicity
  • Ethers, Cyclic* / chemical synthesis
  • Ethers, Cyclic* / toxicity
  • Mice
  • Mutagenicity Tests
  • Mutagens*
  • Salmonella typhimurium / drug effects
  • Urethane* / analogs & derivatives*
  • Urethane* / chemical synthesis
  • Urethane* / toxicity
  • Water

Substances

  • Epoxy Compounds
  • Ethers, Cyclic
  • Mutagens
  • Water
  • Urethane
  • vinyl carbamate
  • vinyl carbamate epoxide