Metabolism and DNA adduct formation of carcinogenic tobacco-specific nitrosamines found in smokeless tobacco products

Research output: Chapter in Book/Report/Conference proceedingChapter

8 Scopus citations

Abstract

Tobacco-specific nitrosamines are the most abundant strong carcinogens in smokeless tobacco products. This chapter focuses on three of the most important of these compounds: N'-nitrosonornicotine (NNN), 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone (NNK), and 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanol (NNAL). The carcinogenic activities of NNN, NNK, and NNAL are discussed, and the metabolic pathways of these carcinogens are presented. Specific metabolite biomarkers have been developed to assess exposure to tobacco-specific nitrosamines in smokeless tobacco users; these are presented and discussed. DNA and protein adduct formation by tobacco-specific nitrosamines are also summarized, based mainly on studies in laboratory animals.

Original languageEnglish (US)
Title of host publicationSmokeless Tobacco Products
Subtitle of host publicationCharacteristics, Usage, Health Effects, and Regulatory Implications
PublisherElsevier
Pages151-166
Number of pages16
ISBN (Electronic)9780128181591
ISBN (Print)9780128181584
DOIs
StatePublished - Jan 21 2020

Bibliographical note

Publisher Copyright:
© 2020 Elsevier Inc. All rights reserved.

Keywords

  • 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanol (NNAL)
  • 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone (NNK)
  • Carcinogenicity
  • DNA adducts
  • Metabolism
  • N'-nitrosonornicotine (NNN)
  • Protein adducts
  • Smokeless tobacco
  • Tobacco-specific nitrosamines
  • Urinary metabolite biomarkers

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