RT Journal Article
SR Electronic
T1 Stereospecific in vivo N-methylation of nicotine in the guinea pig.
JF Drug Metabolism and Disposition
JO Drug Metab Dispos
FD American Society for Pharmacology and Experimental Therapeutics
SP 175
OP 185
VO 13
IS 2
A1 K C Cundy
A1 M Sato
A1 P A Crooks
YR 1985
UL http://dmd.aspetjournals.org/content/13/2/175.abstract
AB 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.