Enantiomeric composition of N'-nitrosonornicotine and N'-nitrosoanatabine in tobacco

Research output: Contribution to journalArticlepeer-review

34 Scopus citations

Abstract

The tobacco-specific nitrosamines N'-nitrosonornicotine (NNN) and N'-nitrosoanatabine (NAT) are found in substantial quantities in unburned tobacco. Although this has been documented in many previous studies, no data are available on the enantiomeric composition of these nitrosamines, which both have a chiral center at their 2'-positions. We used chiral stationary phase gas chromatography with nitrosamine-selective detection to determine the enantiomeric composition of NNN and NAT in moist snuff, chewing tobacco, and cigarette tobacco. (S)-NNN comprised 75.0 ± 8.83% (SD) (n = 12) of total NNN while (S)-NAT comprised 82.6 ± 1.44% (n = 12) of total NAT. Levels of the (S)-enantiomers of NNN and NAT were generally similar to those of the corresponding secondary amines, nornicotine and anatabine, suggesting a precursor to product relationship. Nitrosation of (S)-nicotine at pH 7.0 produced > 99% (S)-NNN. These results suggest that nornicotine is a significant precursor of NNN in tobacco. The results of this study provide new insights into the structures and precursors of tobacco-specific nitrosamines in tobacco products.

Original languageEnglish (US)
Pages (from-to)839-843
Number of pages5
JournalCarcinogenesis
Volume21
Issue number4
DOIs
StatePublished - 2000

Fingerprint Dive into the research topics of 'Enantiomeric composition of N'-nitrosonornicotine and N'-nitrosoanatabine in tobacco'. Together they form a unique fingerprint.

Cite this