PT - JOURNAL ARTICLE AU - M Sato AU - P A Crooks TI - N-Methylnornicotinium ion, a new in vivo metabolite of R-(+)-nicotine. DP - 1985 May 01 TA - Drug Metabolism and Disposition PG - 348--353 VI - 13 IP - 3 4099 - http://dmd.aspetjournals.org/content/13/3/348.short 4100 - http://dmd.aspetjournals.org/content/13/3/348.full SO - Drug Metab Dispos1985 May 01; 13 AB - N-Methylnornicotinium ion has been identified as a metabolite in the urine of male Hartley guinea pigs that had been chronically dosed ip with R-(+)-nicotine. Under similar conditions, S-(-)-nicotine is not biotransformed into this metabolite. The metabolite was isolated and purified by preparative high performance cation-exchange liquid chromatography. The structural identity of the metabolite was determined by UV spectrophotometric analysis and sodium borohydride reduction followed by GLC-mass spectrometric analysis, and Fourier transform 1H NMR spectrometric analysis. The formation of this metabolic product from nicotine represents a unique example of N-demethylation and N-methylation reactions both occurring within the same molecule.