Skip to main page content
U.S. flag

An official website of the United States government

Dot gov

The .gov means it’s official.
Federal government websites often end in .gov or .mil. Before sharing sensitive information, make sure you’re on a federal government site.

Https

The site is secure.
The https:// ensures that you are connecting to the official website and that any information you provide is encrypted and transmitted securely.

Access keys NCBI Homepage MyNCBI Homepage Main Content Main Navigation
. 2023 Mar 20;36(3):334-341.
doi: 10.1021/acs.chemrestox.2c00310. Epub 2023 Mar 10.

A Systematic Review of Analytical Methods for the Separation of Nicotine Enantiomers and Evaluation of Nicotine Sources

Sally Salam  1 , Fatima El-Hajj Moussa  1 , Rachel El-Hage  1   2 , Ahmad El-Hellani  3   4 , Najat Aoun Saliba  1   2
Affiliations

A Systematic Review of Analytical Methods for the Separation of Nicotine Enantiomers and Evaluation of Nicotine Sources

Sally Salam et al. Chem Res Toxicol. .

Abstract

The introduction of synthetic nicotine by the tobacco industry, also promoted as tobacco-free nicotine, presented new challenges for analytical chemists working in tobacco regulatory science to develop and optimize new methods to assess new nicotine parameters, namely enantiomer ratio and source. We conducted a systematic literature review of the available analytical methods to detect the nicotine enantiomer ratio and the source of nicotine using PubMed and Web of Science databases. Methods to detect nicotine enantiomers included polarimetry, nuclear magnetic resonance, and gas and liquid chromatography. We also covered methods developed to detect the source of nicotine either indirectly via determining the nicotine enantiomer ratio or the detection of tobacco-specific impurities or directly using the isotope ratio enrichment analysis by nuclear magnetic resonance (site-specific natural isotope fractionation and site-specific peak intensity ratio) or accelerated mass spectrometry. This review presents an accessible summary of all these analytical methods.

PubMed Disclaimer

Conflict of interest statement

The authors declare no competing financial interest.

Figures

Figure 1
Figure 1
Nicotine enantiomers.
Figure 2
Figure 2
PRISMA diagram summarizing the process of literature selection. Reasons for exclusion of a publication: not reporting the separation of nicotine enantiomers or not developing analytical techniques to differentiate TFN from TDN.
See this image and copyright information in PMC

References

    1. Armstrong D. W.; Wang X.; Ercal N. Enantiomeric composition of nicotine in smokeless tobacco, medicinal products, and commercial reagents. Chirality 1998, 10 (7), 587–591. 10.1002/(SICI)1520-636X(1998)10:7<587::AID-CHIR6>3.0.CO;2-#. - DOI
    1. Saitoh F.; Noma M.; Kawashima N. The alkaloid contents of sixty Nicotiana species. Phytochemistry 1985, 24 (3), 477–480. 10.1016/S0031-9422(00)80751-7. - DOI
    1. Song S.; Myung S.-W. Effective determination of nicotine enantiomers from e-liquids and biological fluids by high performance liquid chromatography (HPLC) using dispersive liquid-liquid microextraction (DLLME). Analytical Science and Technology 2021, 34 (4), 180–190. 10.5806/AST.2021.34.4.180. - DOI
    1. Ji H.; Wu Y.; Fannin F.; Bush L. Determination of tobacco alkaloid enantiomers using reversed phase UPLC/MS/MS. Heliyon 2019, 5 (5), e01719 10.1016/j.heliyon.2019.e01719. - DOI - PMC - PubMed
    1. Zhang H.; Pang Y.; Luo Y.; Li X.; Chen H.; Han S.; Jiang X.; Zhu F.; Hou H.; Hu Q. Enantiomeric composition of nicotine in tobacco leaf, cigarette, smokeless tobacco, and e-liquid by normal phase high-performance liquid chromatography. Chirality 2018, 30 (7), 923–931. 10.1002/chir.22866. - DOI - PubMed

Publication types

MeSH terms