<abstract xmlns="http://www.w3.org/1999/xhtml"><p>Chiral gas chromatography-mass selective detection has been successfully employed in the analysis of secondary alkaloids in selected tobacco materials and cigarette smoke condensate. No extensive sample preparation is involved. A lower detection limit of ~2 % d-nornicotine, d-anabasine and d-anatabine in a mixture of l and d-isomers was achieved. The levels and the enantiomeric ratios of nicotine, nornicotine, anabasine and anatabine varied in different tobacco types. The enantiomeric ratios of nicotine, anabasine and anatabine in mainstream cigarette condensate also varied but were generally representative of the enantiomeric ratios for the alkaloids found in the leaf. The enantiomeric ratio for nornicotine in mainstream cigarette condensate also varied and was not representative of the enantiomeric ratios for the alkaloids found in the leaf. Preferential decomposition or racemization may account for the differences seen in the yields of isomers of nornicotine transferred to the mainstream smoke condensate. An experiment was conducted to determine if the d-nornicotine present in tobacco contributed to the yield of d-nicotine in mainstream smoke condensate. The results of that experiment indicated that the yield of d-nicotine transferred to mainstream smoke did not change significantly when either large levels of endogenous nornicotine were present in the leaf or when large levels of exogenous levels of d-, l-nornicotine were applied to the tobacco rod prior to smoking. The limiting factor in the production of d-nicotine in mainstream cigarette smoke condensate may be the concentration of methyl radicals present to react. Further work must be conducted to unravel the mechanism involved in the production of d-nicotine in cigarette smoke condensate.</p></abstract>

Chiral gas chromatography-mass selective detection has been successfully employed in the analysis of secondary alkaloids in selected tobacco materials and cigarette smoke condensate. No extensive sample preparation is involved. A lower detection limit of ~2 % d-nornicotine, d-anabasine and d-anatabine in a mixture of l and d-isomers was achieved. The levels and the enantiomeric ratios of nicotine, nornicotine, anabasine and anatabine varied in different tobacco types. The enantiomeric ratios of nicotine, anabasine and anatabine in mainstream cigarette condensate also varied but were generally representative of the enantiomeric ratios for the alkaloids found in the leaf. The enantiomeric ratio for nornicotine in mainstream cigarette condensate also varied and was not representative of the enantiomeric ratios for the alkaloids found in the leaf. Preferential decomposition or racemization may account for the differences seen in the yields of isomers of nornicotine transferred to the mainstream smoke condensate. An experiment was conducted to determine if the d-nornicotine present in tobacco contributed to the yield of d-nicotine in mainstream smoke condensate. The results of that experiment indicated that the yield of d-nicotine transferred to mainstream smoke did not change significantly when either large levels of endogenous nornicotine were present in the leaf or when large levels of exogenous levels of d-, l-nornicotine were applied to the tobacco rod prior to smoking. The limiting factor in the production of d-nicotine in mainstream cigarette smoke condensate may be the concentration of methyl radicals present to react. Further work must be conducted to unravel the mechanism involved in the production of d-nicotine in cigarette smoke condensate.

Chiral-Gas Chromatograpy-Selected Ion Monitoring-Mass Selective Detection Analysis of Secondary Alkaloids in Tobacco and Tobacco Smoke

RJ Reynolds Tobacco Company, P.O. Box 1487, Winston-Salem, NC 27102-1487, USA

Contributions to Tobacco & Nicotine Research

This work is licensed under the Creative Commons Attribution-NonCommercial-NoDerivatives 3.0 License.

Chiral gas chromatography-mass selective detection has been successfully employed in the analysis of secondary alkaloids in selected tobacco materials and...

Chiral-Gas Chromatograpy-Selected Ion Monitoring-Mass Selective Detection Analysis of Secondary Alkaloids in Tobacco and Tobacco Smoke

Published Online: Jan 06, 2015

Page range: 35 - 42

Received: Feb 04, 1998

Accepted: Apr 29, 1998

DOI: https://doi.org/10.2478/cttr-2013-0665

© 1998 Beiträge zur Tabakforschung International

This work is licensed under the Creative Commons Attribution-NonCommercial-NoDerivatives 3.0 License.