Journal Article

Enantiomeric composition of <i>N</i>′-nitrosonornicotine and <i>N</i>′-nitrosoanatabine in tobacco

Steven G. Carmella, Edward J. McIntee, Menglan Chen and Stephen S. Hecht

in Carcinogenesis

Volume 21, issue 4, pages 839-843
Published in print April 2000 | ISSN: 0143-3334
Published online April 2000 | e-ISSN: 1460-2180 | DOI: http://dx.doi.org/10.1093/carcin/21.4.839
Enantiomeric composition of N′-nitrosonornicotine and N′-nitrosoanatabine in tobacco

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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.

Keywords: GC-MS-SIM, gas chromatography–mass spectrometry with selected ion monitoring; GC-TEA, gas chromatography with detection by thermal energy analyzer; 5-MeNNN, 5-methyl-N′-nitrosonornicotine; NAB, N′-nitrosoanabasine; NAT, N′-nitrosoanatabine; NNK, 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone; NNN, N′-nitrosonornicotine.

Journal Article.  2917 words.  Illustrated.

Subjects: Clinical Cytogenetics and Molecular Genetics

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