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Synthesis and properties of vinyl carbamate epoxide, a possible ultimate electrophilic and carcinogenic metabolite of vinyl carbamate and ethyl carbamate
Cited 61 time in
Web of Science
Cited 57 time in Scopus
- Authors
- Issue Date
- 1990-06
- Publisher
- Academic Press
- Citation
- Biochemical and Biophysical Research Communications, Vol.169 No.3, pp.1094-1098
- 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. © 1990.
- ISSN
- 0006-291X
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