Identification by proton NMR of N-(hydroxymethyl)-N-methylformamide as the major urinary metabolite of N,N-dimethylformamide in mice.
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.
D000818:Animals; D002849:Chromatography, Gas; D002855:Chromatography, Thin Layer; D004123:Dimethylamines / Q000652:urine; D004126:Dimethylformamide / Q000031:analogs & derivatives* / Q000652:urine*; D009682:Magnetic Resonance Spectroscopy; D008744:Methylamines / Q000652:urine; D051379:Mice; D008808:Mice, Inbred CBA
D004123:Dimethylamines; D008744:Methylamines; C042331:N-hydroxymethyl-N-methylformamide; D004126:Dimethylformamide; C034516:dimethylamine; C027451:methylamine