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
CAS Number	1042688-43-6 Y
3D model (JSmol)	Interactive image
ChemSpider	25047857 N
PubChem CID	24887668
UNII	BXC744Y6CF Y
CompTox Dashboard (EPA)	DTXSID701028454 DTXSID90745433, DTXSID701028454
InChI 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
SMILES CC/C=C\C/C=C\CC[C@H](CNC(=O)CCC[N+](C)(C)C)O
Properties
Chemical formula	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). N verify (what is YN ?) 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.