Chemical Name:N-[(4-Hydroxy-3-methoxyphenyl)methyl]-5Z,8Z,11Z,14Z-eic
osatetraenamide
Biological Activity:
Cannabinoid CB1 and
vanilloid TRPV1 (VR1) agonist (Ki values are 0.5 and 0.3 μM
respectively). Also inhibits the anandamide transporter (IC50 = 3.6 μM).
Analgesic, vasodilatory and anti-inflammatory in vivo.
Melcket al (1999) Unsaturated long-chain N-acyl-vanillyl-amides
(N-AVAMs): vanilloid receptor ligands that inhibit anandamide-facilitated
transport and bind to CB1 receptors. Biochem.Biophys.Res.Comm. 262
275. Szallasi and Di Marzo (2000) New perspectives on enigmatic
vanilloid receptors. TiPS 23 491. Di Marzoet al
(2000) Neurobehavioral activity in mice of N-vanillyl-arachidonyl-amide.
Eur.J.Pharmacol. 406 363.
Analogue of cannabidiol that is a potent agonist at the GPR55 cannabinoid receptor (EC50 values are 13, > 30000 and > 30000 nM for GPR55, CB1 and CB2 receptors respectively). Induces activation of RhoA, cdc42 and rac1.