Determination of (R)-(+)- and (s)-(-)-Nicotine Chirality in Puff Bar E-Liquids by H-1 NMR Spectroscopy, Polarimetry, and Gas Chromatography-Mass Spectrometry

Authors

Anna K. Duell, Portland State University
Paul J. Kerber, Portland State UniversityFollow
Wentai Luo, Portland State UniversityFollow
David H. Peyton, Portland State UniversityFollow

Published In

Chemical Research in Toxicology

Document Type

Citation

Publication Date

7-19-2021

Abstract

Tobacco products generally contain tobacco-derived nicotine (TDN; having ∼99+% (S)-(−)-nicotine). Recent United States regulation has led some producers to transition to synthetic (“tobacco-free”) nicotine. For example, Puff Bar is now marketed with tobacco-free nicotine (TFN; presumed to be racemic). To evaluate the claim that these new products contain TFN, we evaluated the presence of the two nicotine optical isomers by 1H NMR spectroscopy, polarimetry, and gas chromatography–mass spectrometry. Older Puff Bars were found to contain (S)-(−)-nicotine, and newer “TFN” Puff Bars were found to contain both (R)-(+) and (S)-(−) isomers—indicating TFN, albeit with slightly more of the (S)-(−)-nicotine form.

Rights

Copyright © 2021 American Chemical Society

Locate the Document

https://doi.org/10.1021/acs.chemrestox.1c00192

DOI

10.1021/acs.chemrestox.1c00192

Persistent Identifier

https://archives.pdx.edu/ds/psu/36259

Citation Details

Duell, A. K., Kerber, P. J., Luo, W., & Peyton, D. H. (2021). Determination of ( R )-(+)- and ( S )-(−)-Nicotine Chirality in Puff Bar E-Liquids by ¹ H NMR Spectroscopy, Polarimetry, and Gas Chromatography–Mass Spectrometry. Chemical Research in Toxicology, 34(7), 1718–1720. https://doi.org/10.1021/acs.chemrestox.1c00192