Isolation and characterization of N-methyl-N'-oxonicotinium ion, a new urinary metabolite of R-(+)-nicotine in the guinea pig.
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.
D000818:Animals; D001711:Biotransformation; D002851:Chromatography, High Pressure Liquid; D006168:Guinea Pigs; D009682:Magnetic Resonance Spectroscopy; D008297:Male; D013058:Mass Spectrometry; D009538:Nicotine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000302:isolation & purification / Q000378:metabolism* / Q000652:urine; D011726:Pyridinium Compounds; D013056:Spectrophotometry, Ultraviolet; D013237:Stereoisomerism
D011726:Pyridinium Compounds; C050752:N-methyl-N'-oxonicotinium; C047661:N-methylnicotinium; D009538:Nicotine