 | |
| Names | |
|---|---|
| Preferred IUPAC name 2-Aminoethyl (5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoate | |
| Other names O-Arachidonoyl ethanolamine | |
| Identifiers | |
3D model (JSmol) | |
| ChEMBL | |
| ChemSpider |
|
| ECHA InfoCard | 100.158.921 |
| |
| |
| Properties | |
| C22H37NO2 | |
| Molar mass | 347.53468 |
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa). | |
Virodhamine (O-arachidonoyl ethanolamine;O-AEA) is anendocannabinoid and a nonclassiceicosanoid, derived fromarachidonic acid.O-Arachidonoyl ethanolamine isarachidonic acid andethanolamine joined by anester linkage, the opposite of theamide linkage found inanandamide. Based on this opposite orientation, the molecule was named virodhamine from theSanskrit wordvirodha, which means opposition.
Virodhamine acts as anantagonist of theCB1 receptor[1] andagonist of theCB2 receptor. Concentrations of virodhamine in the human hippocampus are similar to those ofanandamide, but they are 2- to 9-fold higher in peripheral tissues that express CB2. Virodhamine lowers body temperature in mice, demonstrating cannabinoid activityin vivo.[2] Virodhamine has also been shown to activateplatelets in whole blood and plasma, although this effect is due not to virodhamine itself, but its enzymatic cleavage to arachidonic acid, which then is converted tothromboxane A2.[3]
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