Nicotelline
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IUPAC name
3,2′:4′,3′′-Terpyridine
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Other names
Nicotellin; 2,4-Dipyridin-3-ylpyridine
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Identifiers | |
3D model (
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CompTox Dashboard (EPA)
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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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Nicotelline is an alkaloid first identified in 1914 as a chemical constituent of tobacco plants (Nicotiana).[2]
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
- ^ a b c The Merck Index (12th ed.). p. 1119. 6609. Nicotelline.
- ^ Noga, Eugen (1914). "The alkaloids in tobacco extract". Fach. Mitt. Tabakregie (1 and 2).
- ^ doi:10.1007/BF00898717.)
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: CS1 maint: multiple names: authors list (link - 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.
- PMID 24125094.)
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: CS1 maint: multiple names: authors list (link