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Determination of (<i>R</i>)-(+)- and (<i>S</i>)-(−)-Nicotine Chirality in Puff Bar E-Liquids by <sup>1</sup>H NMR Spectroscopy, Polarimetry, and Gas Chromatography–Mass Spectrometry

Anna K. Duell, Paul J. Kerber, Wentai Luo, David H. Peyton

2021Chemical Research in Toxicology28 citationsDOIOpen Access PDF

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.

Topics & Concepts

Mass spectrometryChemistryGas chromatographySpectroscopyNuclear magnetic resonance spectroscopyChirality (physics)Analytical Chemistry (journal)Gas chromatography–mass spectrometryBar (unit)ChromatographyPhysicsStereochemistryNuclear physicsChiral symmetry breakingQuantum mechanicsQuarkNambu–Jona-Lasinio modelMeteorologyAnalytical Chemistry and ChromatographyMolecular spectroscopy and chiralityMolecular Sensors and Ion Detection
Determination of (<i>R</i>)-(+)- and (<i>S</i>)-(−)-Nicotine Chirality in Puff Bar E-Liquids by <sup>1</sup>H NMR Spectroscopy, Polarimetry, and Gas Chromatography–Mass Spectrometry | Litcius