Enantiomeric composition of nicotine in smokeless tobacco, medicinal products, and commercial reagents

Chirality

Volumn 10, Issue 7, 1998, Pages 587-591

  Armstrong, Daniel W ^a   Wang, Xiande ^a   Ercal, Nuran ^a  

^a MISSOURI UNIVERSITY OF SCIENCE AND TECHNOLOGY   (United States)

Author keywords

Burley tobacco; Chewing tobacco; Gum; Nasal spray; Snuff; Transdermal patches; Turkish tobacco; Virginia tobacco

Indexed keywords

NICOTINE; NICOTINE GUM; UNCLASSIFIED DRUG;

AEROSOL; CONFERENCE PAPER; DRUG DETERMINATION; DRUG FORMULATION; DRUG PURITY; ENANTIOMER; PRIORITY JOURNAL; SMOKELESS TOBACCO; TOBACCO; TRANSDERMAL PATCH;

EID: 0031687411     PISSN: 08990042     EISSN: None     Source Type: Journal    
DOI: 10.1002/(sici)1520-636x(1998)10:7<587::aid-chir6>3.0.co;2-%23     Document Type: Conference Paper

References (27)

1. Merck Index, 11th ed. Rahway, NJ: Merck & Co., 1989:1030.
2. McIndoo, N.E., Roark, R.C., Busbey, R.L. The insecticide uses of nicotine and tobacco (Publication E-393), Vol. 2, Section 2. In A Bibliography of Nicotine II. Washington, D.C.: U.S. Department of Agriculture, Bureau of Entomology, 1936.
3. Baron, J.A. Cigarette smoking and Parkinson's disease. Neurology 36:1490-1496, 1986.
4. Jones, G.M.M., Sahakian, B.J., Levy, R., Warburton, D.M., Gray, J.A. Effects of acute subcutaneous nicotine on attention, information processing and short-term memory in Alzheimer's disease. Psychopharmacology 108:485-494, 1992.
5. 13C-NMR in the presence of a chiral lanthanide shift reagent. J. Pharmacol. Biomed. Anal. 12:295-299, 1994.
6. Holmstedt, B. In Rand, M.J., Thuran, K. (eds.): The Pharmacology of Nicotine. Washington, D.C.: IRL Press, 1988:61-88.
7. Bownam, E.R., McKennis, Jr., H., Martin, B. A convenient method for the preparation of racemic nicotine. Synth. Commun. 12:871-879, 1982.
8. Gorrod, J.W., Jenner, P. The metabolism of tobacco alkaloids. Essays in Toxicol. 6:35-78, 1975.
9. Barlow, R.B., Hamilton, J.T. The stereospecificity of nicotine. Brit. J. Pharmacol. 25:206-212, 1965.
10. Aceto, M.D., Martin, B.R., Uwaydah, I.M., May, E.L., Harris, L.S., Izazola-Conde, C., Dewey, W.L., Bradshaw, T.J., Vincek, W.C. Optically pure (+)-nicotine and (+)-nicotine and biological comparisons with (-)-nicotine. J. Med. Chem. 22:174-177, 1979.
11. Ikushima, S., Muramatsu, I., Sakakibara, Y., Yokatani, K., Fujiwara, M. The effects of d-nicotine and l-isomer on nicotinic receptors. J. Pharmacol. Exp. Ther. 222:463-470, 1982.
12. Aceto, M.D., Martin, B.R., May, E.L. Nicotine enantiomers: Pharmacological and biochemical effects. In CRC Handbook of Stereoisomers: Drugs in Psychopharmacology. Boca Raton, Florida: CRC Press, Inc., 67-78, 1984.
13. Meltzer, L.T., Rosecrans, J.A., Aceto, M.D., Harris, L.S. Discriminative stimulus properties of the optical isomers of nicotine. Psychopharmacology 68:283-286, 1980.
14. Risner, M.E., Cone, E.J., Benowitz, N.L., Jacob, P. III. Effects of the stereoisomers of nicotine and nornicotine on schedule-controlled responding and physiological parameters of dogs. J. Pharmacol. Exp. Ther. 244:807-813, 1988.
15. Martin, B.R. Stereoselectivity of nicotine's central effects and its relationship to pain and cardiovascular function. In Advances in Mental Science. New York: Plenum Press, 4:301-316, 1987.
16. Nwosu, C.G., Crooks, P.A. Species variation and stereoselectivity in the metabolism of nicotine enantiomer. Xenobiotica 18:1361-1372, 1988.
17. Jacob, P. III, Benowitz, N.L., Copeland, J.R., Risner, M.E., Cone, E.J. Disposition kinetics of nicotine and continine enantiomers in rabbits and beagle dogs. J. Pharm. Sci. 77:396-400, 1988.
18. Copeland, J.R., Adem, A., Jacob, P. III, Nordberg, A. A comparison of the binding of nicotine and nornicotine stereoisomers to nicotinic binding sites in rat brain cortex. Naunyn-Schmiedeberg's Arch. Pharmacol. 343:123-127, 1991.
19. Yildiz, D., Ercal, N., Armstrong, D.W. Effects of nicotine enantiomers on Chinese hamster ovary (CHO) cells. Free Radical Biological and Medicine, 1998, in press.
20. Crooks, P.A., Godin, C.S., Pool, W.F. Enantiomeric purity of nicotine in tobacco smoke condensate. Med. Sci. Res. 20:879-880, 1992.
21. Perfetti, T.A., Swadesh, J.K. On-line determination of the optical purity of nicotine. J. Chromatogr. 543:129-135, 1991.
22. Klus, H., Kuhn, H. Untersuchungen uber die optische aktivitat des rauchnikotins. Fachliche Mitt. Oesterr. Tabakregie 17:331-336, 1977.
23. Zukowski, J., Tang, Y., Berthod, A., Armstrong, D.W. Investigation of a circular dichroism spectrophotometer as a liquid chromatography detector for enantiomers: sensitivity, advantages and limitations. Anal. Chim. Acta 258:83-92, 1992.
24. Armstrong, D.W., Spino, L.A., Han, S.M., Seeman, J.I., Secor, H.V. Enantiomeric resolution of racemic nicotine and nicotine analogues by microcolumn liquid chromatography with β-cyclodextrin inclusion complexes. J. Chromatogr. 411:490-493, 1987.
25. Demetriou, D., Rustemeier, K., Voncken, P., Schepers, G. HPLC separation of the enantiomers of nicotine and nicotine-like compounds. Chirality 5:300-302, 1993.
26. Tang, Y., Zielinski, W.L., Bigott, H.M. Separation of nicotine and nornicotine enantiomers via normal phase HPLC on derivatized cellulose chiral stationary phases. Chirality 10:364-369, 1998.
27. Saitoh, F., Noma, M., Kawashima, N. The alkaloid contents of 60 Nicotiana species. Phytochem. 24:477-480, 1985.