Kinetics of nornicotine and anabasine nitrosation in relation to N′-nitrosonornicotine occurrence in tobacco and to tobacco-induced cancer

Sidney S. Mirvish, James Sams, Stephen S. Hecht

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Abstract

The kinetics of nornicotine and anabasine nitrosa-tion, studied in aqueous solution, obeyed equations typical for the nitrosation of aliphatic secondary amines, with third-order stoichiometric rate constants of 1.15 (nornicotine) and 0.86 (anabasine) m–2 sec–1. The similarity of the two rate constants suggested that the nitrosonornicotine occurring in tobacco arises from nicotine rather than nornicotine, because tobacco contains anabasine but apparently does not contain nitro-soanabasine. The high rate constants suggested that in vivo nitrosation of these secondary amines may constitute a hazard to tobacco smokers and chewers, in addition to that presented by preformed nitrosonornicotine.

Original languageEnglish (US)
Pages (from-to)1211-1213
Number of pages3
JournalJournal of the National Cancer Institute
Volume59
Issue number4
DOIs
StatePublished - Oct 1977

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