Open Access

Chiral-Gas Chromatography-Selected Ion Monitoring-Mass Selective Detection Analysis of Tobacco Materials and Tobacco Smoke


Cite

1. Barlow, R. B., and J. T. Hamilton: The stereo-specificity of nicotine; Br. J. Pharmacol. 25 (1965) 206-212.Search in Google Scholar

2. Aceto, M. D., B. R. Martin, I. M. Uwaydah, E. L. May, L. S. Harris, C. Izazola-Conde, W.L. Dewey, T. J. Bradshaw, and W. C. Vincek: Opticallypure (+)-nicotinefrom ± nicotine and biological comparisons with (-)- nicotine; J. Med. Chem. 22 (1979) 174-177.Search in Google Scholar

3. Ikushima, S., I. Muramatsu, Y. Sakakibara, K. Yokatani, and M. J. Fujiwara: The effects of d-nicotine and /-isomer on nicotinic receptors; J. Pharmacol. Exp. Ther. 222 (1982) 463-470.Search in Google Scholar

4. Holmstedt, B.: The Use of Enantiomers in Biological Studies: A Historical Review; in: Chirality and biological activity, edited by Frank, H., Holmstedt, B. and B. Testa, New York, Alan R. Liss, 1990, pp 1-14.Search in Google Scholar

5. Risner, M. E., E. J. Cone, N. L. Benowitz, and P. I. Jacob, III: Effects of the stereoisomers of nicotine and nornicotine on schedule-controlled responding and physiological parameters of dogs; J. Pharmacol. Exp. Ther. 244 (1988) 807-813.Search in Google Scholar

6. Clark, M. S. G., M. J. Rand, and S. Vanow: Comparison of pharmacological activity of nicotine and related alkaloids occurring in cigarette smoke; Arch. Int. Pharmacodyn. 156 (1965) 363-379.Search in Google Scholar

7. Reavill, C, P. Jenner, R. Kumar, and I. P. Stolerman: High affinity binding of [3H]-(-) -nicotine to rat brain membranes and its inhibition by analogs of nicotine; Neuropharmacol. 27 (1988) 235-241.Search in Google Scholar

8. Posselt, W., and L. Reimann: Chemical investi-gation of tobacco and the preparation of the characteristic active principle of this plant; Magazin f. Pharmazie, 24 (1828) 138-61.Search in Google Scholar

9. Manske, R. H. F., and H.L. Holmes: The alkaloids: chemistry and physiology, Vol. 1; Aca-demic Press, New York, 1950.Search in Google Scholar

10. Holmstedt, B., M.J. Rand and K. Thuran: The pharmacology of nicotine; IRL Press, Washington, D. C, 1988, pp 61-88.Search in Google Scholar

11. Mclndoo, N. E., R.C. Roark, and R.L. Busbey: A bibliography of nicotine, Part II: The insecti-cidal uses of nicotine and tobaccoQ (Publication E-392), Vol. 2, Section 1, U. S. Department of Agriculture, Bureau of Entomology, Washington, D. C, 1936.Search in Google Scholar

12. Pictet, A., and A. Rotschy: Synthese des nico-tins; Chem. Ber. 37 (1904), 1225-1235.Search in Google Scholar

13. Gorrod, J. W., and P. Jenner: The metabolism of tobacco alkaloids; Essays in Toxicol. 6 (1975) 35-78.10.1016/B978-0-12-107606-1.50008-2Search in Google Scholar

14. Martin, B. R., and M. D. Aceto: Nicotine binding sites and their localization in the central nervous system; Neurosci. Biobehav. Rev. 5 (1981) 473-478.Search in Google Scholar

15. Meltzer, L. T., J. A. Rosecrans, M. D. Aceto, and L. S. Harris: Discriminativestimulusproperties of the optical isomers of nicotine; Psychopharmacology. 68 (1980) 283-286.Search in Google Scholar

16. Budavari, A., CNeil, M. J., Smith, A., and Heckelman, P. E.: The Merck Index, llth Edition, Merck & Co. Inc., Rahway, NJ, USA, Nos. 655, 661, 6434, 6631, 1989.Search in Google Scholar

17. Baron, J. A.: Cigarette smoking and Parkinson's disease; Neurology 36 (1986) 1490-1496.Search in Google Scholar

18. Sahakian, B., G. Jones, R. Levy, J. Gray, and D. Warburton: The effects of nicotine on attention information processing and short-term memory in patients with dementia of the Alzheimer type; Br. J. Psychiatry 154 (1989) 797.Search in Google Scholar

19. Koenig, P.: Die Entdeckung des reinen Nikotins im Jahre 1828 an der Universitat Heidelberg durch Reimann und Posselt mit Beschreibung ihrer Vorlaufer und mit Abbildungen; Arthur Geist, Bremen, 1940.Search in Google Scholar

20. Wilbert, J.: Tobacco and shamanism in South America; Yale University Press, New Haven, CT, USA, chapter 4, 1987.Search in Google Scholar

21. Macht, D. I.: Pharmacological synergism of stereoisomers; Proc. Natl. Acad., Sci., 15 (1929) 63-70.10.1073/pnas.15.1.6352240716587450Search in Google Scholar

22. Copeland, J. R., A. Adem, P. I. Jacob, III, and A. A. Nordberg: A comparison of the binding of nicotine and nornicotine stereoisomers to nicotinic binding sites in rat brain cortex; Arch. Pharmacol. 343 (1991) 123-127.Search in Google Scholar

23. Spath, E., C. S. Hicks, and E. Zajic: d-Nornicotine, an alkaloid of Duboisia hopwoodii F. v. Muell; Chem. Ber. 68 (1935) 1388-1393.Search in Google Scholar

24. Spath, E., C. S. Hicks, and E. Zajic: d-Nornicotine; Chem. Ber. 69 (1936) 250-251.10.1002/cber.19360690207Search in Google Scholar

25. Spath, E. and E. Zajic: Tobacco bases. III. /-Nornicotine; Chem. Ber. 68 (1935) 1667-1670.Search in Google Scholar

26. Smith, C. R.: Occurrence of /-nornicotine in Nicotiana sylvestris; J. Econ. Entomol. 30 (1937) 724-727.Search in Google Scholar

27. Jeffrey, R. N., and T.C. Tso: Qualitative differ-ences in the alkaloid fraction of cured tobaccos; Ag. Food Chem. 3 (1955) 680-682.Search in Google Scholar

28. Pelegri Galiana, M. R., and J. M. Viguera Lobo: Alkaloids of Nicotiana glauca (alcaloides de la Nicotiana glauca r. grah); Anales de Fisica y Ojuimica. 60 (5B) (1964) 419-422.Search in Google Scholar

29. Kłus, H., and H. Kuhn: Untersuchungen uber die optische Aktivitat des Rauchnikotins; Fachliche Mitt. Oesterr. Tabakregie. 17 (1977) 331-336.Search in Google Scholar

30. Pictet, A. and P. Crepieux: Phenyl- and pyridyl-pyrroles and the constitution of nicotine; Chem. Ber. 28 (1895) 1904-1912.Search in Google Scholar

31. Leete, E., and M. R. Chedekel: The aberrant formation of (-)-N-methylanabasine from n-methyl-deltal-piperideinium chloride in Nicotiana tabacum and N. glauca; Phytochem. 11 (1972) 2751-2756.Search in Google Scholar

32. Kisaki, T. and E. Tamaki: Phytochemical studies of tobacco alkaloids. X. Degradation of the tobacco alkaloids and their optical rotatory changes in tobacco plants; Phytochem. 5 (1966) 293-300.Search in Google Scholar

33. Chavdarian, C. G., E. B. Sanders, and R. L. Bass-field: Synthesis of optically active nicotinoids; J. Org. Chem. 47 (1982) 1069-1073.Search in Google Scholar

34. Mahboodi, S., and W. Wiegrebe: Enantioselective synthesis of some Nicotiana alkaloids; Arch. Pharm. 321 (1988) 175-178.Search in Google Scholar

35. Jacob, III, P.: Resolution of 5-bromonornicotine. Synthesis of (R)- and (S) -nornicotine of high enantiomeric purity; J. Org. Chem. 47 (1982) 4165-4167.Search in Google Scholar

36. Bowman, E. R., H. McKennis, Jr., and B. R. Martin: A convenient method for the preparation of racemic nicotine; Synth. Commun. 12 (1982) 871-879.Search in Google Scholar

37. Seeman, J. L, C. G. Chavdarian, and H. V. Secor: Synthesis of the enantiomers of nornicotine; J. Org. Chem. 50 (1985) 5419-5421.Search in Google Scholar

38. Garvey, D. S., J. T. Wasicak, M. W. Decker, J. D. Brioni, M. J. Buckley, J. P. Sullivan, G. M. Carrera, M. W. Holladay, S. O. Arneric, and M. J. Williams: Novel isoxazoles which interact with brain cholinergic channel receptors have intrinsic cognitive enhancing and anxiolytic activities; J. Med. Chem. 37 (1994) 1055-1059.Search in Google Scholar

39. Perfetti, T. A., and J. K. Swadesh: On-line deter-mination of the optical purity of nicotine; J. Chromatogr. 543 (1991) 129-136.Search in Google Scholar

40. Perfetti, T. A.: Structural study of nicotine salts; Beitr. Tabakforsch. Int. 12 (1983) 43-54.Search in Google Scholar

41. Scherer, G., and H. Kłus: Cigarette smoking and compensation; Recent Adv. Tob. Sci. 23 (1997) 197-245.Search in Google Scholar

42. Baker, R. R.: A review of pyrolysis studies to unravel reaction steps in burning tobacco; J. Anal. Applied Pyrolysis. 11 (1997) 555-573.Search in Google Scholar

43. Lewis, D. A., I. Colbeck, and D. C. Mariner: Dilution of mainstream tobacco smoke and its effects upon the evaporation and diffusion of nicotine; J. Aerosol Sci. 26(5) (1995) 841-846.Search in Google Scholar

44. Lewis, D. A., I. Colbeck, and D. C. Mariner: Diffusion denuder method for sampling vapor-phase nicotine in mainstream tobacco smoke; Anal. Chem. 66 (1994) 3525-3527.Search in Google Scholar

45. Crooks, P. A., C. S. Godin, and W. F. Pool: Enantiomeric purity of nicotine in tobacco smoke condensate; Med. Sci Res. 20 (1992) 879-880.Search in Google Scholar

46. Katsuyama, A., S. Maeda, Y. Mikami, S. Uchida, Y. Obi and T. J. Kisaki: Bulk preparation of r -(+) - nicotine from a racemic mixture by contin-uous culture with an isolated Pseudomonas putida; J. Ferment. Technol. 61 (3) (1983) 269-274.Search in Google Scholar

47. Edwards, W. B. and R. McCuen: Preparation of optically pure (R) - (+) - nicotine studies on the microbial degradation of nicotinoids; J. Org. Chem. 48 (1983) 2484-2487.Search in Google Scholar

48. Yoshida, D. and H. Tomita: Optical rotary power of nicotine in the smoke of cigarette; NipponSembaiKoshaChuo. 117 (1975) 125-127.Search in Google Scholar

49. Cundy, K. C, M. Sato and P. A. Crooks: Stereo-specific in vivo N-methylation of nicotine in the guinea pig; Drug Metabol. Disposit. 13 (1985) 175-185.Search in Google Scholar

50. Ravard, A., and P. A. Crooks: Chiral purity determination of tobacco alkaloids and nicotine-like compounds by proton NMR spectroscopy in the presence of 1,l'-binaphtyl-2,2'-diylphosphoric acid; Chirality 8 (1996) 295-299.Search in Google Scholar

51. Testa, B., and P. Jenner: Circular dichroic determination of the preferred conformation of nicotine and related chiral alkaloids in aqueous solution; Molecular Pharmacol. 9 (1973) 10-16.Search in Google Scholar

52. Tomita, A., E. Ochiai, H. Hirai and S. Makishima: The effect of hydrogen chloride on the optical rotation of nicotine; J. Org. Chem. 31 (1966) 4307-4308.Search in Google Scholar

53. Kobashi, Y., and M. Watanabe: Investigation on separatingconditions of nicotine homologues by gas chromatography; Japan Analyst 13 (1964) 1243-1248.Search in Google Scholar

54. Jacob, III, P., N. L. Benowitz, J. R. Copeland, M. E. Risner, and E. J. Cone: Disposition kinet-ics of nicotine and cotinine enantiomers in rabbits and beagle dogs; J. Pharm. Sci. 77 (1988) 396-400.Search in Google Scholar

55. Armstrong, D. W., L. A. Spino, S. M. Han, J. I. Seeman and H. V. Secor: Enantiomeric resolution of racemic nicotine and nicotine analogs by microcolumn liquid chromatography with beta-cyclodextrin inclusion; J. Chromatogr. 411 (1987) 490-493.Search in Google Scholar

56. Seeman, J. L, H. V. Secor, D. W. Armstrong, K. D. Timmons, and T. J. Ward: Enantiomeric resolution and chiral recognition of racemic nicotine and nicotine analogues by beta-cyclodextrin complexation; Anal. Chem. 60 (1988) 2120-2127.Search in Google Scholar

57. Demetriou, D., K. Rustemeier, P. Voncken, and G. Schepers: HPLC separation of the enantiomers of nicotine and nicotine-like compounds; Chirality 5 (1993) 300-302.Search in Google Scholar

58. Seeman, J. L, H. V. Secor, D. W. Armstrong, K. D. Ward and T. J. Ward: Separation of homolo-gous and isomeric alkaloids related to nicotine on a beta-cyclodextrin-bonded phase; J. Chromatography 483 (1989) 169-178.Search in Google Scholar

59. Cundy, K. C. and P. A. Crooks: Unexpected phenomenon in the high-performance liquid chromatographic analysis of racemic carbon-14-labeled nicotine: Separation of enatiomers in a totally achiral system; J. Chromatography 281 (1983) 17-33.Search in Google Scholar

60. Armstrong, D. W., G. L. Bertrand, K. D. Ward, T. J. Ward, H. V. Secor, and J. I. Seeman: Evalu-ation of the effect of organie modifier and pH on retention and selectivity in reversed-phase liquid chromatographic separation of alkaloids on a cyclodextrin-bonded phase; Anal. Chem. 62 (1990) 332-338.Search in Google Scholar

61. Abdoh, Y. and H. Pirelahi: Alkaloid content of tobacco seeds; Naturę 204 (1964) 791-792.Search in Google Scholar

62. Ohashi, M., I. Morishima, and T. Yonezawa: Application of proton NMR shift reagents to the stereochemical analysis of nicotine; Buli. Chem. Soc. Jap., 44 (1971) 576-577.Search in Google Scholar

63. Bassfield, R. L.: The interaction of lanthanide shift reagents with cationic sites; a proton and “ C NMR study of the solution geometry of nicotine N-methiodide; J. Amer. Chem. Soc. 105 (1983) 4168-4172.Search in Google Scholar

64. Diana, J. N., and Vaught, A.: The research cigarette; The Tobacco and Health Research Institute, Lexington, Kentucky, USA, 1990.Search in Google Scholar

65. Katsuyama, A., H. Kaneko, S. Maeda, Y. Tsujino, S. Uchida, S. Shibata, Y. Mikami, Y. Obi and T. Kisaki: Racemization of nicotine and preparation of i-nicotine; CORESTA Symposium Winston-Salem (1982).Search in Google Scholar

66. Pool, W. F., C. S. Godin, and P. A. Crooks: Nicotine racemization during cigarette smoke; Toxicologist 5 (1985) 232.Search in Google Scholar

67. Cundy, K. C, C. S. Godin, and P. A. Crooks: Stereospecific in vitro N-methylation of nicotine in guinea pig tissues by an S-adenosylmethionine dependent N-methyltransferase; Biochem. Pharmacol. 34 (1985) 281-284.Search in Google Scholar

68. Rodgman, A.: FTC tar and nicotine in cigarette mainstream smoke: a retrospective; Recent Adv. Tob. Sci. 23 (1997) 5-74.Search in Google Scholar

69. Bicchi, C, V. Manzin, A. DNAmato, and P. Rubiolo: Cyclodextrin derivatives in GC separation of enantiomers of essential oil, aroma and flavor compounds; Flav. Frag. J., 10 (1995) 127-137.Search in Google Scholar

70. Kisaki, T., S. Maeda, A. Koiwai, Y. Mikami, T. Sasaki and H. Matsushita: Transformation of tobacco alkaloids; Beitr. Tabakforsch., 9(5) (1978) 308-316.Search in Google Scholar

71. Coleman, III, W. M., T. A. Perfetti: The roles of amino acids and sugars in the production of volatile materials in microwave heated tobacco dust suspensions; Beitr. Tabakforsch. Int. 17 (1997) 75-95.Search in Google Scholar

72. Coleman, III, W. M., J. L. White and T. A. Perfetti: Investigation of a unique commonality from a wide rangę of natural materials as viewed from the Maillard reaction perspective; J. Sci. Food Agric. 70 (1996) 405-412.Search in Google Scholar

73. Gordon, B. M., and G. H. Greene: Determination of nicotine nornicotine and other second-ary aminę alkaloids in tobacco; 35th Tobacco Chemists’ Research Conference, paper 25, 1981.Search in Google Scholar

74. Miller, J. C. and Miller, J. N., Statistics for Analytical Chemistry, Second Edition, Ellis Horwood Limited, Chichester, 1988, 115-117.Search in Google Scholar

75. Browne, C. L., The Design of Cigarettes, Hoechst Celanese Corporation, Charlotte, NC, USA, 1990, 44-47.Search in Google Scholar

eISSN:
1612-9237
Language:
English
Publication timeframe:
4 times per year
Journal Subjects:
General Interest, Life Sciences, other, Physics