Virodhamine

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 ;
3D model (JSmol)	Interactive image;
ChEMBL	ChEMBL187349 ;
ChemSpider	4650158 ;
ECHA InfoCard	100.158.921
IUPHAR/BPS	5554;
PubChem CID	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- Key: DLHLOYYQQGSXCC-DOFZRALJSA-N ; 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 their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

Virodhamine (O-arachidonoyl ethanolamine; O-AEA) is an endocannabinoid 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.

Virodhamine acts as an antagonist of the CB₁ receptor^[1] and agonist of the CB₂ receptor. Concentrations of virodhamine in the human hippocampus are similar to those of anandamide, but they are 2- to 9-fold higher in peripheral tissues that express CB₂. Virodhamine lowers body temperature in mice, demonstrating cannabinoid activity in vivo.^[2] Virodhamine has also been shown to activate platelets 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 to thromboxane A2.^[3]

References

^ Steffens, Marc; Zentner, Josef; Honegger, Jurgen; Feuerstein, Thomas J. (2005). "Binding affinity and agonist activity of putative endogenous cannabinoids at the human neocortical CB₁ receptor". Biochemical Pharmacology. 69 (1). Elsevier: 169–178. doi:10.1016/j.bcp.2004.08.033. Retrieved 15 Jul 2025.
^ Porter AC, Sauer JM, Knierman MD, et al. (2002). "Characterization of a novel endocannabinoid, virodhamine, with antagonist activity at the CB1 receptor". J. Pharmacol. Exp. Ther. 301 (3): 1020–4. doi:10.1124/jpet.301.3.1020. PMID 12023533. S2CID 26156181. Retrieved 2007-10-31.
^ Brantl, S. Annette; Khandoga, Anna L.; Siess, Wolfgang (2014). "Mechanism of platelet activation induced by endocannabinoids in blood and plasma". Platelets. 25 (3). Taylor & Francis: 151–161. doi:10.3109/09537104.2013.803530. Retrieved 15 Jul 2025.

[1] Steffens, Marc; Zentner, Josef; Honegger, Jurgen; Feuerstein, Thomas J. (2005). "Binding affinity and agonist activity of putative endogenous cannabinoids at the human neocortical CB₁ receptor". Biochemical Pharmacology. 69 (1). Elsevier: 169–178. doi:10.1016/j.bcp.2004.08.033. Retrieved 15 Jul 2025.

[pmid12023533-2] Porter AC, Sauer JM, Knierman MD, et al. (2002). "Characterization of a novel endocannabinoid, virodhamine, with antagonist activity at the CB1 receptor". J. Pharmacol. Exp. Ther. 301 (3): 1020–4. doi:10.1124/jpet.301.3.1020. PMID 12023533. S2CID 26156181. Retrieved 2007-10-31.

[3] Brantl, S. Annette; Khandoga, Anna L.; Siess, Wolfgang (2014). "Mechanism of platelet activation induced by endocannabinoids in blood and plasma". Platelets. 25 (3). Taylor & Francis: 151–161. doi:10.3109/09537104.2013.803530. Retrieved 15 Jul 2025.

[1]

[2]

[3]

See also

References