EVIDENCE OF STEREOSPECIFICITY IN THE INVIVO METHYLATION OF [C-14] (+/-)-NICOTINE IN THE GUINEA-PIG

  • 1 January 1984
    • journal article
    • research article
    • Vol. 12  (6) , 755-759
Abstract
In vivo metabolism of [14C]nicotine to N-methylnicotinium ion in the guinea pig appears to be a sterespecific biotransformation, involving only the R-(+)-isomer. The detection and quantitation of urinary radiolabeled nicotine metabolites after i.p. injection of either [N-14CH3](.+-.)-nicotine or [2''-14C](.+-.)-nicotine, was carried out on an HPLC [high-performance liquid chromatography] cation-exchange analytical system. Utilizing the recently discovered phenomenon of differential enantiomeric association, the stereochemistry of the methylation pathway was determined. Significant differences in the tissue distribution of 14C label from the [N-14CH3]-vs. [2''-14C]nicotine-treated animals were observed 24 h after nicotine administration. An unidentified metabolite with high affinity on cation-exchange chromatography, was detected as a metabolite of [2''-14C](.+-.)-nicotine, but was not observed as a metabolite of [N-14CH3](.+-.)-nicotine.

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