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In vivo and in vitro oxidative biotransformation of dimethylformamide in rat

Authors
Journal
Chemico-Biological Interactions
0009-2797
Publisher
Elsevier
Publication Date
Volume
50
Issue
3
Identifiers
DOI: 10.1016/0009-2797(84)90040-1
Keywords
  • Metabolism
  • Rat
  • Dimethylformamide
  • N-Hydroxymethyl
  • N-Methylformamide
  • N-Methylformamide
  • Hydroxyl Radicals

Abstract

Abstract In rats and in humans, dimethylformamide (DMF) is mainly metabolized into N-hydroxymethyl- N-methylformamide (DMF-OH). The in vitro oxidation of DMF by rat liver microsomes is decreased in the presence of catalase and superoxide dismutase. The radical scavengers, dimethylsulfoxide (DMSO), tertiary butyl alcohol ( t-butanol), aminopyrine, hydroquinone and trichloroacetonitrile reduce the oxidation of DMF to DMF-OH in vitro and in vivo. Conversely, DMF inhibits the demethylation of DMSO, t-butanol and aminopyrine. The addition of iron-EDTA to the incubation system induces the production of N-methylformamide (NMF) from DMF. These results support the hypothesis that the metabolic pathway leading from DMF to DMF-OH and NMF involves hydroxyl radicals. Superoxide radical and hydrogen peroxide take part in the metabolic process. DMF is preferentially metabolized into DMF-OH. NMF appears mainly when the production of hydroxyl radicals is stimulated, the methyl group being recovered as formic acid.

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