Identification by proton NMR of N-(hydroxymethyl)-N-methylformamide as the major urinary metabolite of N,N-dimethylformamide in mice

Life Sci. 1986 Feb 24;38(8):719-24. doi: 10.1016/0024-3205(86)90586-2.

Abstract

Urine samples from mice which had received N,N-dimethylformamide were investigated by high field 1H-NMR spectroscopy. The most prominent signals in the N-CH3 region had chemical shifts identical with those of N,N-dimethylformamide (delta 2.85, 3.01) and N-(hydroxymethyl)-N-methylformamide (delta 2.91, 3.05). Resonances downfield of delta 7.5 (from formyl protons) also coincided with those of the reference formamides. When [14C]methyl-labelled N,N-dimethylformamide was injected and urine samples investigated by radio thin layer chromatography, the major area of radioactivity corresponded to the Rf of N-(hydroxymethyl)-N-methylformamide. Dimethylamine and methylamine were found to be minor metabolites of N,N-dimethylformamide.

MeSH terms

  • Animals
  • Chromatography, Gas
  • Chromatography, Thin Layer
  • Dimethylamines / urine
  • Dimethylformamide / analogs & derivatives*
  • Dimethylformamide / urine*
  • Magnetic Resonance Spectroscopy
  • Methylamines / urine
  • Mice
  • Mice, Inbred CBA

Substances

  • Dimethylamines
  • Methylamines
  • N-hydroxymethyl-N-methylformamide
  • Dimethylformamide
  • dimethylamine
  • methylamine