Nicotelline Explained

Nicotelline is an alkaloid first identified in 1914 as a chemical constituent of tobacco plants (Nicotiana).^[1]

The chemical structure of nicotelline wasn't elucidated until 1956, when it was determined that nicotelline is a terpyridine consisting of three linked pyridine rings. This structure was confirmed by laboratory synthesis.^{[2] [3]} Nicotelline has the molecular formula . It is a crystalline solid with a melting point of 147-148 °C. It is soluble in hot water, chloroform, ethanol, and benzene.

Nicotelline has long been known to be a constituent of tobacco smoke.^[4] As such, it has recently been proposed as a biomarker or environmental tracer for tobacco smoke.^[5]

Notes and References

1. The alkaloids in tobacco extract . Noga, Eugen . Fach. Mitt. Tabakregie . 1914 . 1 and 2.
2. Nicotellin and the synthesis of a new terpyridyl . Kuffner, Friedrich; Kaiser, Ernst . Monatshefte für Chemie . 1954 . 85 . 896–905 . 10.1007/BF00898717 .
3. Constitution of nicotelline . Kuffner, Friedrich; Faderl, Norbert . Monatshefte für Chemie . 1956 . 87 . 71–81 . 10.1007/BF00903590 .
4. The alkaloids of tobacco smoke and the constitution of nicotelline . Kuffner, F. . Fachliche Mitteilungen der Oesterreichischen Tabakregie . 1956 . 18–19 .
5. Nicotelline: A Proposed Biomarker and Environmental Tracer for Particulate Matter Derived from Tobacco Smoke . Jacob, Peyton; Goniewicz, Maciej L.; Havel, Christopher M.; Schick, Suzaynn F.; Benowitz, Neal L. . Chemical Research in Toxicology . 2013 . 26 . 11 . 1615–1631 . 10.1021/tx400094y . 24125094 . 3929594 .