Virodhamine

Virodhamine
IUPAC name	2-aminoethyl (5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoate
Other names	O-Arachidonoyl ethanolamine
Identifiers
CAS number	443129-35-9
PubChem	5712057
SMILES	CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(=O)OCCN
Properties
Molecular formula	C22H37NO2
Molar mass	347.53468
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox disclaimer and references

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Virodhamine (O-arachidonoyl ethanolamine) is an endocannibinoid and a nonclassic eicosanoid, derived from arachidonic acid. O-Arachidonoyl ethanolamine is arachidonic acid and ethanolamine joined by an ester linkage, the opposite of the amide linkage found in anandamide. Based on this opposite orientation, the molecule was named virodhamine from the Sanskrit word virodha, which means opposition. It is an antagonist of the CB1 receptor and an agonist of CB2. Concentrations of virodhamine in the human hippocampus are similar to anandamide, but they were 2- to 9-fold higher in peripheral tissues that express CB2. Virodhamine lowers body temperature in mice, demonstrating cannabinoid activity in vivo.