Species Variation in the Metabolism of R-(+)- and S-(-)-Nicotine by α-C- andN-Oxidationin vitro
- 1 January 1973
- journal article
- research article
- Published by Taylor & Francis in Xenobiotica
- Vol. 3 (9) , 573-580
- https://doi.org/10.3109/00498257309151545
Abstract
1. Marked species, but not sex differences, were observed in the metabolism of R-(+)- and S-(-)-nicotine to cotinine and the diastereoisomeric nicotine-1′-N-oxides by liver 10 000 × g supernatant preparations from rats, rabbits, mice, guinea-pigs and hamsters. 2. S-(-)-nicotine formed predominantly R,S-cis-nicotine-1′-N-oxide, whereas R-(+)-nicotine gave predominantly S,R-trans-nicotine-1′-N-oxide; stereoselective metabolism to cotinine also occurred. A stereo-selective site for the N-oxidation of nicotine is proposed to explain these results.Keywords
This publication has 13 references indexed in Scilit:
- Characterization of the Diastereoisomers of Nicotine-1′-N-Oxide, a Metabolite of Nicotine, and Other Possible Oxidation Products by Nuclear Magnetic Resonance SpectroscopyXenobiotica, 1973
- Factors Affecting thein vitroMetabolism of R-(+)-and S-(-)-Nicotine by Guinea-pig Liver PreparationsXenobiotica, 1973
- A possible relation between pKa1 and lipid solubility and the amounts excreted in urine of some tobacco alkaloids given to manJournal of Pharmacy and Pharmacology, 1972
- The analysis of nicotine-1‘-N-oxide in urine, in the presence of nicotine and cotinine, and its application to the study of in vivo nicotine metabolism in manJournal of Pharmacy and Pharmacology, 1971
- Selective inhibition of alternative oxidative pathways of nicotine metabolism in vitroChemico-Biological Interactions, 1971
- Enzymic oxidation of (—)-nicotine by guinea-pig tissues in vitroBiochemical Pharmacology, 1971
- The metabolism of nicotine into two optically-active stereoisomers of nicotine-1′-oxide by animal tissues in vitro and by cigarette smokersBiochemical Pharmacology, 1970
- Demonstration of n-epimers in the salt of a piperidine derivative in solutionTetrahedron Letters, 1965
- Tertiary Amine Oxide Rearrangements. III. The Mechanism of the Demethylation of NicotineJournal of the American Chemical Society, 1964
- The colorimetric estimation of formaldehyde by means of the Hantzsch reactionBiochemical Journal, 1953