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Nicotelline

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Nicotelline
Names
IUPAC name 3,2′:4′,3′′-Terpyridine
Other names Nicotellin; 2,4-Dipyridin-3-ylpyridine
Identifiers
CAS Number
3D model (JSmol)
ChemSpider
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C15H11N3/c1-3-13(10-16-6-1)12-5-8-18-15(9-12)14-4-2-7-17-11-14/h1-11HKey: OILSPHJMIPYURT-UHFFFAOYSA-N
SMILES
  • C1=CC(=CN=C1)C2=CC(=NC=C2)C3=CN=CC=C3
Properties
Chemical formula C15H11N3
Molar mass 233.274 g·mol
Melting point 147–148 °C (297–298 °F; 420–421 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Infobox references
Chemical compound

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

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. Nicotelline has the molecular formula C15H11N3. 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. As such, it has recently been proposed as a biomarker or environmental tracer for tobacco smoke.

References

  1. ^ The Merck Index (12th ed.). p. 1119. 6609. Nicotelline.
  2. Noga, Eugen (1914). "The alkaloids in tobacco extract". Fach. Mitt. Tabakregie (1 and 2).
  3. ^ Kuffner, Friedrich; Kaiser, Ernst (1954). "Nicotellin and the synthesis of a new terpyridyl". Monatshefte für Chemie. 85: 896–905. doi:10.1007/BF00898717.{{cite journal}}: CS1 maint: multiple names: authors list (link)
  4. Kuffner, Friedrich; Faderl, Norbert (1956). "Constitution of nicotelline". Monatshefte für Chemie. 87: 71–81. doi:10.1007/BF00903590.{{cite journal}}: CS1 maint: multiple names: authors list (link)
  5. Kuffner, F. (1956). "The alkaloids of tobacco smoke and the constitution of nicotelline". Fachliche Mitteilungen der Oesterreichischen Tabakregie: 18–19.
  6. 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.{{cite journal}}: CS1 maint: multiple names: authors list (link)
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