Nicotelline

Nicotelline

Nicotelline

Chemical compound

Nicotelline is an alkaloid first identified in 1914 as a chemical constituent of tobacco plants (Nicotiana).[2]

Quick Facts Names, Identifiers ...

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

  1. [1]
    The Merck Index (12th ed.). p. 1119. 6609. Nicotelline.
  2. [2]
    Noga, Eugen (1914). "The alkaloids in tobacco extract". Fach. Mitt. Tabakregie (1 and 2).
  3. [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. [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. [5]
    Kuffner, F. (1956). "The alkaloids of tobacco smoke and the constitution of nicotelline". Fachliche Mitteilungen der Oesterreichischen Tabakregie: 18–19.
  6. [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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