Nicotelline

Nicotelline
Names
	IUPAC name 3,2′:4′,3′′-Terpyridine
	Other names Nicotellin; 2,4-Dipyridin-3-ylpyridine
Identifiers
CAS Number	494-04-2;
3D model (JSmol)	Interactive image;
ChemSpider	61431;
PubChem CID	68123;
UNII	7AO144V8IZ;
CompTox Dashboard (EPA)	DTXSID40197781 ;
	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/h1-11H Key: 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−1
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 [77 °F], 100 kPa). Infobox references

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).
^ ^a ^b 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)
^ 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)
^ 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.{{cite journal}}: CS1 maint: multiple names: authors list (link)

[merck-1] The Merck Index (12th ed.). p. 1119. 6609. Nicotelline.

[Noga-2] Noga, Eugen (1914). "The alkaloids in tobacco extract". Fach. Mitt. Tabakregie (1 and 2).

[Kuffner-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)

[Kuffner2-4] 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)

[Kuffner3-5] Kuffner, F. (1956). "The alkaloids of tobacco smoke and the constitution of nicotelline". Fachliche Mitteilungen der Oesterreichischen Tabakregie: 18–19.

[Jacob-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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