Enantiomeric composition of nornicotine, anatabine, and anabasine in tobacco

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

Levels of (S)-N'-Nitrosonornicotine in U.S. Tobacco Products

“…In tobacco, nicotine is >99% (S)-enantiomer (Armstrong, Wang, & Ercal, 1998), and nitrosation of nicotine of such enantiomeric composition produces >99% (S)-NNN (Carmella et al, 2000). On the other hand, nornicotine was shown to contain 70%-96% (S)-nornicotine (Armstrong, Wang, Lee, & Liu, 1999;Carmella et al, 2000), and it has been previously noted that the enantiomeric composition of NNN in tobacco indicates that nornicotine, and not nicotine, is the major precursor of NNN in tobacco (Carmella et al, 2000). Our results further reinforce that hypothesis.…”

Metabolism and Disposition Kinetics of Nicotine

“…They all are derived from nicotine; NЈ-nitrosonornicotine is also derived from nornicotine (Hecht, 1998). Unlike nicotine, the minor alkaloids anatabine, nornicotine, and anabasine and their N-nitroso derivatives are present to a substantial degree as the (R)-isomer (about 16, 20, and 42%, respectively) in tobacco products (Armstrong et al, 1999;Carmella et al, 2000).…”

Enantiomeric analysis of anatabine, nornicotine and anabasine in commercial tobacco by multi-dimensional gas chromatography and mass spectrometry

“…All four alkaloids are chiral. Naturally occurring nicotine is predominately the S-(−)-isomer while the minor alkaloids (anatabine, nornicotine, and anabasine) are enantiomeric mixtures [3].…”

“…Because of the much higher concentration of nicotine and the presence of other matrix-related compounds, the enantiomeric distribution of the minor Nicotiana alkaloids has not been well studied. Two prominent papers that described alkaloids in the plant were inconsistent in their findings, with Perfetti and Coleman [5] reporting that the enantiomeric distribution for nornicotine varied between different tobacco while Armstrong et al [3] found that the enantiomeric ratios for the three minor alkaloids were similar in different tobacco.…”