Nicotelline
Nicotelline is an alkaloid first identified in 1914 as a chemical constituent of tobacco plants (Nicotiana).[2]
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Names | |
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IUPAC name
3,2′:4′,3′′-Terpyridine | |
Other names
Nicotellin; 2,4-Dipyridin-3-ylpyridine | |
Identifiers | |
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Properties | |
C15H11N3 | |
Molar mass | 233.274 g·mol−1 |
Melting point | 147–148 °C (297–298 °F; 420–421 K)[1] |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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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.[3] This structure was confirmed by laboratory synthesis.[3][4] Nicotelline has the molecular formula C15H11N3. It is a crystalline solid with a melting point of 147-148 °C.[1] It is soluble in hot water, chloroform, ethanol, and benzene.[1]
Nicotelline has long been known to be a constituent of tobacco smoke.[5] As such, it has recently been proposed as a biomarker or environmental tracer for tobacco smoke.[6]
References
- The Merck Index (12th ed.). p. 1119. 6609. Nicotelline.
- Noga, Eugen (1914). "The alkaloids in tobacco extract". Fach. Mitt. Tabakregie (1 and 2).
- Kuffner, Friedrich; Kaiser, Ernst (1954). "Nicotellin and the synthesis of a new terpyridyl". Monatshefte für Chemie. 85: 896–905. doi:10.1007/BF00898717.
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: CS1 maint: multiple names: authors list (link) - Kuffner, Friedrich; Faderl, Norbert (1956). "Constitution of nicotelline". Monatshefte für Chemie. 87: 71–81. doi:10.1007/BF00903590.
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: CS1 maint: multiple names: authors list (link) - Kuffner, F. (1956). "The alkaloids of tobacco smoke and the constitution of nicotelline". Fachliche Mitteilungen der Oesterreichischen Tabakregie: 18–19.
- Jacob, Peyton; Goniewicz, Maciej L.; Havel, Christopher M.; Schick, Suzaynn F.; Benowitz, Neal L. (2013). "Nicotelline: A Proposed Biomarker and Environmental Tracer for Particulate Matter Derived from Tobacco Smoke". Chemical Research in Toxicology. 26 (11): 1615–1631. doi:10.1021/tx400094y. PMC 3929594. PMID 24125094.
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: CS1 maint: multiple names: authors list (link)
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