Virodhamine

Names
Preferred IUPAC name 2-Aminoethyl (5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoate
Other names O-Arachidonoyl ethanolamine
Identifiers
CAS Number	287937-12-6 N
3D model (JSmol)	Interactive image
ChEMBL	ChEMBL187349 Y
ChemSpider	4650158 Y
ECHA InfoCard	100.158.921
IUPHAR/BPS	5554
PubChemCID	5712057
CompTox Dashboard(EPA)	DTXSID601018179
InChI InChI=1S/C22H37NO2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-22(24)25-21-20-23/h6-7,9-10,12-13,15-16H,2-5,8,11,14,17-21,23H2,1H3/b7-6-,10-9-,13-12-,16-15- Y Key: DLHLOYYQQGSXCC-DOFZRALJSA-N Y InChI=1/C22H37NO2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-22(24)25-21-20-23/h6-7,9-10,12-13,15-16H,2-5,8,11,14,17-21,23H2,1H3/b7-6-,10-9-,13-12-,16-15- Key: DLHLOYYQQGSXCC-DOFZRALJBB
SMILES O=C(OCCN)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC
Properties
Chemical formula	C22H37NO2
Molar mass	347.53468
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa). N verify (what is YN ?) Infobox references

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. It acts as anantagonist of theCB₁ receptor 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.^[1]

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