RT Journal Article
SR Electronic
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
FD American Society for Pharmacology and Experimental Therapeutics
SP 574
OP 579
VO 14
IS 5
A1 W F Pool
A1 A A Houdi
A1 L A Damani
A1 W J Layton
A1 P A Crooks
YR 1986
UL http://dmd.aspetjournals.org/content/14/5/574.abstract
AB 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.