TY - JOUR T1 - Isolation and characterization of N-methyl-N'-oxonicotinium ion, a new urinary metabolite of R-(+)-nicotine in the guinea pig. JF - Drug Metabolism and Disposition JO - Drug Metab Dispos SP - 574 LP - 579 VL - 14 IS - 5 AU - W F Pool AU - A A Houdi AU - L A Damani AU - W J Layton AU - P A Crooks Y1 - 1986/09/01 UR - http://dmd.aspetjournals.org/content/14/5/574.abstract N2 - Biotransformation of both R-(+)-nicotine and R-(+)-N-methyl-nicotinium acetate in male Hartley guinea pigs affords a new quaternary amine metabolite, which was isolated and purified from urine by preparative HPLC. The structural analysis of the metabolite was carried out using UV spectrophotometry, direct thermospray mass spectrometry, and Fourier transform 1H-NMR spectroscopy. The structure of the metabolite was confirmed by synthesis and shown to be a mixture of the cis-1'S,2'R-, and trans-1'R,2'R-diastereomers of N-methyl-N'-oxonicotinium ion, formed in the ratio 1.6:1.0, respectively. S-(-)-Nicotine under similar conditions does not undergo this biotransformation. ER -