Skip to main content
SpringerLink
Log in

The In Vitro Metabolic Fate of (S)-Nicotine

  • Chapter
Effects of Nicotine on Biological Systems

Part of the book series: APS Advances in Pharmacological Sciences ((APS))

Summary

The primary in vitro metabolic transformations for the tobacco alkaloid (S)-nicotine proceed by N’-oxidation, oxidative N-dealkylation and ring α-carbon oxidation. The aldehyde oxidase catalyzed oxidation of the unstable Δ1′,5′-iminium intermediate formed by ring α-carbon oxidation generates (S)-cotinine which in turn is bio-oxidized in vivo to a variety of metabolites. This paper reviews these pathways and presents recent findings on the interaction of the Δ1′,5′ -iminium intermediate with monoamine oxidase B and the fate of the resulting pyrrolic metabolite β-nicotyrine.

This is a preview of subscription content, log in via an institution to check access.

Access this chapter

Log in via an institution
Chapter
USD 29.95
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
eBook
USD 39.99
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
Softcover Book
USD 54.99
Price excludes VAT (USA)
  • Compact, lightweight edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info

Tax calculation will be finalised at checkout

Purchases are for personal use only

Institutional subscriptions

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  • Benowitz, N.D. (1988) In: The Pharmacology of Nicotine. (M.J. Rand and K. Thurau, Eds), IRL Press, Oxford, pp. 3–18.

    Google Scholar 

  • Brandange, S. and Lindbloom, L. (1979) Biochem. Biophys, Res. Comm. 91, 991–996.

    Article  Google Scholar 

  • Carlson, T., Trager, W.F., Peterson, L. and Castagnoli, N., Jr., ISSX Abstract, San Diego, CA, October, 1990.

    Google Scholar 

  • Chiba, K., Peterson, L.A., Castagnoli, K.P., Trevor, A.J., and Castagnoli, N. Jr. (1985) Drug Met. Disp. 12, 342–347.

    Google Scholar 

  • Dagne, E. and Castagnoli, N., Jr. (1972a) J. Med. Chem. 15, 356–360.

    Article  Google Scholar 

  • Dagne, E. and Castagnoli, N., Jr. (1972b) J. Med. Chem. 15, 840–841.

    Article  Google Scholar 

  • Damani, L.A., Pool, W.L., Crooks, P.A., Kaderlik, R.K., and Ziegler, D.M. (1988) Mol. Pharmacol. 22. 702–705.

    Google Scholar 

  • Jacob, P. Ill, Benowitz, N.L., and Shulgin, A. T. (1988) Biochem. Behav. 22, 249–253.

    Article  Google Scholar 

  • Jenner, P., Gorrod, J.W., and Beckett, A. H. (1973) Xenobiotica 2, 563–572.

    Article  Google Scholar 

  • Kyerematen, G.A., Owens, G.F., Chattopadhyay, B., deMethizy, J.D., and Vessel, E.S. (1988) Drug Meta. Disp. 16, 823–828.

    Google Scholar 

  • Kyerematen, G.A., Taylor, L. H., DeBethizy, J.D., and Vesell, E.S. (1988) Drug Met. Disp. 16, 125–129.

    Google Scholar 

  • Mattammal, M.B., Lakshimi, V.M., Zenser, T.V., and Davis, B.B. (1987) J. Pharmacol. Exp. Ther. 242, 827–832.

    Google Scholar 

  • McCoy, G.D., DeMarco, G.J., and Koop, D.R. (1989) Biochem. Pharmacol. 28, 1185–1188.

    Article  Google Scholar 

  • McCoy, G.D., Howard, P.C., and DeMarco, G.J. (1986) Biochem. Pharmacol. 22, 2767–2773.

    Article  Google Scholar 

  • Murphy, P.J. (1972) J. Biol. Chem. 212, 2796–2800.

    Google Scholar 

  • Nakayama, H.T., Nakashima,T., and Kurogochi, Y. (1982) Biochem. Biophys. Res. Comm. 108, 200–205.

    Article  Google Scholar 

  • Neurath, G.B. and Plein, F.G. (1987) J. Chrom. 415, 400–406.

    Article  Google Scholar 

  • Neurath, G.B., Dünger, M., Krenz, O., Orth, D., and Pein, F.G. (1988) Klin. Wochenschr. 66 (Suppl XI), 2–4.

    Google Scholar 

  • Nguyen, T.L., Gruenke, L.D. and Castagnoli, N., Jr. (1976) J. Med. Chem. 19, 1168–1169.

    Article  Google Scholar 

  • Nguyen, T-L., Gruenke, L.D., and Castagnoli, N., Jr. (1979) J. Med. Chem. 22, 259–263.

    Article  Google Scholar 

  • Nwosu, Z. and Crooks, P.A. (1988) Xenobiotica 12, 1361–1372.

    Article  Google Scholar 

  • O’Doherty, S., Revans, A., C.L. Smith, M. McBride, and M. Cooke (1988) J. High Res. Chrom. & Chrom Comm. 11, 723–726.

    Article  Google Scholar 

  • Obach, R.S. and Van Vunakis, H. (1988) Biochem. Pharmacol. 22, 4601–4604.

    Article  Google Scholar 

  • Ortiz de Montellano, P. R. (1989) TiPS l0, 354–359.

    Google Scholar 

  • Overton, M., Hickman, J.A., Threadgill, M.D., Vaughn, K. and Gescher, A. (1985) Biochem. Pharmacol. 34, 2055–2061.

    Article  Google Scholar 

  • Peterson, L.A., Trevor, A., and Castagnoli, N. Jr. (1987) J. Med. Chem. 30, 249–254.

    Article  Google Scholar 

  • Peterson, L.A.. and Castagnoli, N., Jr. (1988) J. Med. Chem. 3l, 637–640.

    Article  Google Scholar 

  • Shigenaga, M.K., Kim., B.H., Caldera-Munoz, P., Cairns, T., Jacob, P. Ill, Trevor, A.J., and Castagnoli, N., Jr., (1989) Chem Res. Tox. 2, 282–287.

    Article  Google Scholar 

  • Shigenaga, M.K., Trevor, A. J., and Castagnoli, N., Jr. (1987) Drug. Metab. Disp. 16, 397–402.

    Google Scholar 

  • Williams, D.E., Ding, X., and Coon, M. J. (1990a) Biochem. Biophy. Res. Comm. 166, 945–952.

    Article  Google Scholar 

  • Williams, D.E., Shigenaga, M.K., and Castagnoli, N., Jr. (1990b) Drug. Met. Disp. 18, in press.

    Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Department of Chemistry, Virginia Polytechnic Institute and State University, Blacksburg, Virginia, 24061, USA

    N. Castagnoli Jr.

  2. Department of Pharmacology, University of California, San Francisco, California, 94143, USA

    M. Shigenaga & A. Trevor

  3. Department of Medicinal Chemistry, University of Washington, Seattle, Washington, 98195, USA

    T. Carlson & W. F. Trager

Authors
  1. N. Castagnoli Jr.
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. M. Shigenaga
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. T. Carlson
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. W. F. Trager
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. A. Trevor
    View author publications

    You can also search for this author in PubMed Google Scholar

Editor information

Editors and Affiliations

  1. Forschungsrat Rauchen und Gesundheit, Königswinterer Straße 550, D-W-5300, Bonn 3, Germany

    Franz Adlkofer M.D. (Professor of Medicine, Scientific Secretary of the Research Council on Smoking and Health) (Professor of Medicine, Scientific Secretary of the Research Council on Smoking and Health)

  2. Physiologisches Institut, Universität München, Pettenkofer Straße 12, D-W-8000, München 2, Germany

    Klaus Thurau M.D. (Professor of Physiology, Chairman of the Research Council on Smoking and Health) (Professor of Physiology, Chairman of the Research Council on Smoking and Health)

Rights and permissions

Reprints and permissions

Copyright information

© 1991 Birkhäuser Verlag Basel

About this chapter

Cite this chapter

Castagnoli, N., Shigenaga, M., Carlson, T., Trager, W.F., Trevor, A. (1991). The In Vitro Metabolic Fate of (S)-Nicotine. In: Adlkofer, F., Thurau, K. (eds) Effects of Nicotine on Biological Systems. APS Advances in Pharmacological Sciences. Birkhäuser Basel. https://doi.org/10.1007/978-3-0348-7457-1_4

Download citation

  • DOI: https://doi.org/10.1007/978-3-0348-7457-1_4

  • Publisher Name: Birkhäuser Basel

  • Print ISBN: 978-3-0348-7459-5

  • Online ISBN: 978-3-0348-7457-1

  • eBook Packages: Springer Book Archive

Publish with us

Policies and ethics

Search

Navigation