TY - JOUR T1 - N-Methylnornicotinium ion, a new in vivo metabolite of R-(+)-nicotine. JF - Drug Metabolism and Disposition JO - Drug Metab Dispos SP - 348 LP - 353 VL - 13 IS - 3 AU - M Sato AU - P A Crooks Y1 - 1985/05/01 UR - http://dmd.aspetjournals.org/content/13/3/348.abstract N2 - 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. ER -