title: N-Methylnornicotinium ion, a new in vivo metabolite of R-(+)-nicotine.
abstract: 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.
authors.forename: M
authors.initials: M
authors.lastname: Sato
authors.forename: P A
authors.initials: PA
authors.lastname: Crooks
mesh_terms: D000818:Animals; D001711:Biotransformation; D006168:Guinea Pigs; D008297:Male; D008745:Methylation; D009538:Nicotine / Q000031:analogs & derivatives* / Q000378:metabolism*; D013237:Stereoisomerism
chemical_list: D009538:Nicotine; C045981:N-methylnornicotinium