Complanine

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.

Complanine
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
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 ☒N
    Key: QYFDYRHORFAECH-SVCKQPKZSA-O ☒N
  • 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).
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Infobox references
Eurythoe complanata

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.

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.
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