title: Stereospecific in vivo N-methylation of nicotine in the guinea pig.
abstract: R-(+)-[3H-N'-CH3]N-methylnicotinium ion has been identified as a urinary metabolite of ip administered R-(+)-[3H-N'-CH3]nicotine in the guinea pig. Under similar conditions, S-(-)-[3H-N'-CH3]nicotine is not converted to the corresponding N-methylated metabolite. R-(+)-N-methylnicotinium salt was isolated from the urine of guinea pigs that had been chronically dosed ip with R-(+)-nicotine. The identification and stereochemical analysis of this metabolite were carried out using analytical and preparative cation exchange high pressure liquid chromatography and chemical reduction followed by GLC-mass spectrometric analysis and 1H NMR spectroscopy. The results show that nicotine is stereospecifically biotransformed into an N-methylated urinary metabolite in the guinea pig.
authors.forename: K C
authors.initials: KC
authors.lastname: Cundy
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; D002851:Chromatography, High Pressure Liquid; D008401:Gas Chromatography-Mass Spectrometry; D006168:Guinea Pigs; D009682:Magnetic Resonance Spectroscopy; D008297:Male; D008745:Methylation; D009538:Nicotine / Q000378:metabolism* / Q000652:urine; D013056:Spectrophotometry, Ultraviolet; D013237:Stereoisomerism; D014018:Tissue Distribution
chemical_list: D009538:Nicotine