Abstract
Literature reports on the optical purity of the minor alkaloids in tobacco leaf and its products often contradict one another. The enantiomeric compositions of nornicotine, anatabine, and anabasine were measured using gas chromatography/mass spectrometry (GC/MS) (with a chiral stationary phase) in three types of tobacco leaf (Burley, Turkish, and Virginia); three types of smokeless tobacco (loose-leaf, dry snuff, and moist snuff); and four types of cigarettes. Regardless of the tobacco type or product, anabasine always had the highest relative percentage of the minor (R)-(+)-enantiomeric component (between 40 and 46% vs. 54-60% of the (S)-(-)-enantiomer). Of the four common tobacco alkaloids, nicotine seems to have the highest enantiomeric excess (e.e.) while anabasine has the lowest (in the tobacco leaf and tobacco products analyzed). Nornicotine and anatabine have intermediate e.e. values.
Recommended Citation
D. W. Armstrong et al., "Enantiomeric Composition of Nornicotine, Anatabine, and Anabasine in Tobacco," Chirality, vol. 11, no. 1, pp. 82 - 84, Wiley, Jan 1999.
The definitive version is available at https://doi.org/10.1002/(SICI)1520-636X(1999)11:1<82::AID-CHIR14>3.0.CO;2-C
Department(s)
Chemistry
Publication Status
Full Access
Keywords and Phrases
Chiral stationary phase; Derivatized cyclodextrin; GC/MS; Minor tobacco alkaloids; Selected ion monitoring
International Standard Serial Number (ISSN)
0899-0042
Document Type
Article - Journal
Document Version
Citation
File Type
text
Language(s)
English
Rights
© 2024 Wiley, All rights reserved.
Publication Date
13 Jan 1999
