Metabolism, pharmacological effects and analytical detection of synthetic nicotine
In the case a consumer product contains racemic Synthetic Nicotine , 50% of the nicotine content is present as R-nicotine. Little is known about the pharmacological and metabolic effects of R-nicotine in humans. Metabolic studies comparing the fate of R-nicotine in several animal species revealed stereoselec- tive differences in the formation of oxidative metabolites and stereospecific N-methylation of nicotine enantiomers.
The degradation kinetics of the resulting S-cotinine and R-cotinine also differed. In contrast to S-nicotine, R-nicotine did not induce weight loss in rats and did not trigger epinephrine release. R-nicotine is a significantly less potent (~10-fold) agonist of nicotine receptors than S-nicotine, however, both stereoisomers interfere with the production of certain lipid mediators involved in regulation of inflammation. Hellinghausen et al devised a methodology to determine the concentrations of both R-nicotine and S-nicotine in E-liquids, nicotine patches and tablets, using a chiral stationary phase for enantioselective separation by High Performance Liquid Chro- matography (HPLC), circular dichroism detection and electro- spray ionisation mass spectrometry.
The authors reported that one product contained twice as much total nicotine (sum of R-nicotine and S-nicotine) as stated on the product label, effec- tively listing only the S-nicotine strength, while for other prod- ucts the amount listed on the label was equivalent to the total nicotine amount, with effectively half present as S-nicotine. These confusing labelling practices may expose unknowing users to high levels of R-nicotine, or to lower S-nicotine levels they are used to, causing them to purchase products with higher total nicotine content. The authors also detected impurities that require further characterisation.
With highly pure synthetic S-nicotine available now in some E-liquids, how can synthetic S-nicotine be differentiated from tobacco-derived S-nicotine? The compounds are chemically iden- tical and cannot be differentiated by standard analytical techniques. Comparison of carbon isotope content may offer a solution. Carbon exists as three isotopes 12C, 13C and 14C, with 14C decaying with a half-life of 5700 years, a property used in radiocarbon dating of 14 biological materials. C is constantly replenished in the atmosphere and integrated into living plant matter, including tobacco plants and their alkaloids. In contrast, synthetic products, often produced from petrochemicals formed millions of years ago, have much lower 14C content. For example, a 14C analytical method has been developed to differentiate naturally sourced vanillin, a treasured flavourant, from vanillin produced from fossil sources.
Depending on the metabolic pathways involved, natural products may also contain a higher ratio of 13C. High-temperature liquid chromatography coupled to isotope ratio mass spectrometry (HT-RPLC/IRMS) has become a standard approach to identify foods adulterated with synthetic additives, capable of differentiating between natural and synthetic caffeine, ethanol and sugars, among other chemicals.
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