Enantiomeric composition of nornicotine, anatabine, and anabasine in tobacco

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. Chirality 11:82–84, 1999. © 1999 Wiley-Liss, Inc.