Stereospecific in vivo N-methylation of nicotine in the guinea pig.
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.
Cundy
K C
KC
Sato
M
M
Crooks
P A
PA
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
D009538:Nicotine