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Effects of Nicotine on Biological Systems pp 89–101Cite as

Relevance of Nicotine-Derived N-Nitrosamines in Tobacco Carcino-Genesis

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

Summary

Tobacco-specific N-nitrosamines (TSNA) are formed from the Nicotiana alkaloids by N-nitrosation. Among identified TSNA are powerful animal carcinogens, namely N′-nitrosonornicotine (NNN), 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone (NNK) and 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanol (NNAL). In animals and in human tissues these nitrosamines are metabolically activated by α-hydroxylation to highly reactive species which form adducts with protein and DNA. These three TSNA contribute significantly to the increased risk of snuff dippers for oral cancer and to the risk of smokers for cancer of the lung and oral cavity and likely also for cancer of the esophagus and pancreas. Chemopreventive approaches towards reduction of risk of TSNA-related cancer are discussed, as is the need for developing methods for the reduction of TSNA in tobacco and tobacco smoke. Future research should concentrate on biomarkers for the exposure of tobacco users to TSNA, the DNA binding of TSNA in humans, and on the question of endogenous formation of TSNA.

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Authors and Affiliations

  1. Naylor Dana Institute for Disease Prevention, American Health Foundation, 1 Dana Road, Valhalla, New York, 10595, USA

    D. Hoffmann, A. Rivenson, F.-L. Chung & S. S. Hecht

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  1. D. Hoffmann
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  2. A. Rivenson
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  3. F.-L. Chung
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  4. S. S. Hecht
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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)

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© 1991 Birkhäuser Verlag Basel

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Hoffmann, D., Rivenson, A., Chung, FL., Hecht, S.S. (1991). Relevance of Nicotine-Derived N-Nitrosamines in Tobacco Carcino-Genesis. 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_13

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  • DOI: https://doi.org/10.1007/978-3-0348-7457-1_13

  • Publisher Name: Birkhäuser Basel

  • Print ISBN: 978-3-0348-7459-5

  • Online ISBN: 978-3-0348-7457-1

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