Enantiomeric composition of nicotine in tobacco leaf, cigarette, smokeless tobacco, and e‐liquid by normal phase high‐performance liquid chromatography

Abstract

Evaluating the source of nicotine in e-liquid is a problem. Tobacco-derived nicotine contains predominantly (S)-(-)-nicotine, whereas tobacco-free nicotine products may not. Thus, we developed a new normal phase high-performance liquid chromatography method to determinate the enantiomeric composition of nicotine in 10 kinds of flue-cured tobacco, 3 kinds of burley, 1 kind of cigar tobacco, 2 kinds of oriental tobacco, 5 kinds of Virginia cigarette, 5 kinds of blend cigarette, 10 kinds of e-liquid, and 4 kinds of smokeless tobacco. The amount of (R)-(+)-nicotine ranged from ~0.02% to ~0.76% of total nicotine. An e-liquid sample had the highest level of (R)-(+)-nicotine. The extraction and purification processes used to obtain commercial (S)-(-)-nicotine from the tobacco do not decrease the amount of (R)-(+)-nicotine in tobacco. So the amount of (R)-(+)-nicotine in samples in our work were the same as tobacco samples.

Moving targets: how the rapidly changing tobacco and nicotine landscape creates advertising and promotion policy challenges

“…Tobacco plants produce only one of the two chemical enantiomers of nicotine (S-nicotine), while synthetic nicotine is commonly a racemic 50:50 mixture of the two chemical enantiomers (S-nicotine and R-nicotine). 105 Little is known about the R-nicotine enantiomer because previously human exposure to and intake of R-nicotine was minimal 105 ; the substantial presence of R-nicotine in synthetic nicotine products has unknown health impact. 9 FDA has not made a decision about how it may regulate synthetic nicotine products, 101 exemplifying how a regulatory agency may lag behind the commercial market, constrained by outdated and narrow legislation.…”

“…Some products labelled ‘tobacco-free nicotine’ claim to contain synthetically produced nicotine and others state the nicotine is derived from tobacco but purified. Tobacco plants produce only one of the two chemical enantiomers of nicotine (S-nicotine), while synthetic nicotine is commonly a racemic 50:50 mixture of the two chemical enantiomers (S-nicotine and R-nicotine) 105. Little is known about the R-nicotine enantiomer because previously human exposure to and intake of R-nicotine was minimal105; the substantial presence of R-nicotine in synthetic nicotine products has unknown health impact 9…”

Synthetic nicotine has arrived

“…Tobacco leaf contains >99% S-nicotine. 8 A search for the term 'synthetic nicotine' in the Truth Tobacco Industry Documents revealed that the industry considered the use of synthetic nicotine already in the 1960s. A document by British American Tobacco proposed the addition of synthetic nicotine for adjustment of the nicotine/tar ratio in combustible cigarettes.…”

Emerging ENDS products and challenges in tobacco control toxicity research

“…Studies enabling the testing of products for synthetic versus tobacco nicotine, such as the determination of the enantiomeric excess of the synthetic enantiomers, are needed for validating industry claims that they are not using TDN 41–43. However, the distinction between synthetic and TDN has become more challenging, as new laboratory syntheses of enantiomerically pure nicotine have recently been patented 1.…”