Complanine

Last updated
Complanine
Complanine structure.svg
Names
Preferred IUPAC name
4-{[(2R,5Z,8Z)-2-Hydroxyundeca-5,8-dien-1-yl]amino}-N,N,N-trimethyl-4-oxobutan-1-aminium
Other names
  • (−)-Complanine
  • (R)-(−)-Complanine
Identifiers
3D model (JSmol)
ChemSpider
PubChem CID
UNII
  • InChI=1S/C18H34N2O2/c1-5-6-7-8-9-10-11-13-17(21)16-19-18(22)14-12-15-20(2,3)4/h6-7,9-10,17,21H,5,8,11-16H2,1-4H3/p+1/b7-6-,10-9-/t17-/m1/s1 X mark.svgN
    Key: QYFDYRHORFAECH-SVCKQPKZSA-O X mark.svgN
  • InChI=1/C18H34N2O2/c1-5-6-7-8-9-10-11-13-17(21)16-19-18(22)14-12-15-20(2,3)4/h6-7,9-10,17,21H,5,8,11-16H2,1-4H3/p+1/b7-6-,10-9-/t17-/m1/s1
    Key: QYFDYRHORFAECH-SKOIHYTMBD
  • CC/C=C\C/C=C\CC[C@H](CNC(=O)CCC[N+](C)(C)C)O
Properties
C11H22NO+
Molar mass 184.302 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
X mark.svgN  verify  (what is  Yes check.svgYX mark.svgN ?)
Eurythoe complanata Eurythoe complanata.jpg
Eurythoe complanata

Complanine is a quaternary ammonium compound isolated from the marine fireworm Eurythoe complanata . It causes an inflammatory effect upon contact with the skin or mucous membranes.

Occurrence

It was previously known that handling the fireworm caused it to release a chemical that induces inflammation of the skin of marine predators and mammals (including humans). Complanine was the first compound isolated from the fireworm which causes these effects. The chemical structure of Complanine was determined by spectroscopical methods [1] and the absolute configuration was confirmed with a total synthesis. [2]

It is presumed that this compound's function is to deter predators of the fireworm.

Related Research Articles

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References

  1. Kazuhiko Nakamura; Yu Tachikawa; Makoto Kitamura; Osamu Ohno; Masami Suganuma; Daisuke Uemura (2008). "Complanine, an inflammation-inducing substance isolated from the marine fireworm Eurythoe complanata". Org. Biomol. Chem. 6 (12): 2058–2060. doi:10.1039/b803107j. PMID   18528565.
  2. Nakamura, Kazuhiko; Tachikawa, Yu; Uemura, Daisuke (2009). "(−)-Complanine, an inflammatory substance of marine fireworm: a synthetic study". Beilstein Journal of Organic Chemistry. 5: 12. doi:10.3762/bjoc.5.12. PMC   2686394 . PMID   19478919.