58493-49-5

Olvanil is a structural analog of capsaicin, which is the noxious active component of hot peppers of the Capsicum genus. It is the amide of vanillylamine and oleic acid. Olvanil acts as an agonist at the vanilloid receptor, VR1, inducing desensitization analgesia in rat and mouse models of pain. Olvanil has complex interactions with the cannabinoid system, in that it potentiates the agonist activity of endogenous cannabinoids by inhibiting the reuptake of arachidonyl ethanolamide (AEA). Olvanil is a more potent reuptake inhibitor than AM404, which is commonly used for this purpose (50% inhibition of reuptake at 10 μM versus 12% for AM404 at the same dose). Olvanil is also a CB₁ agonist, but does not bind to CB₂ receptors or inhibit fatty acid amide hydrolase. The overall activity of olvanil in most models is that of an analgesic, but it is unclear how these effects are mediated by VR1, the CB₁ receptor, or other components of the endogenous pain sensation system.

Analgesic.

Olvanil is a TRPV1 agonist more potent than capsaicin.

ChEBI: N-Vanillyloleamide is a member of methoxybenzenes and a member of phenols.

Potent vanilloid receptor agonist (pEC 50 values are 8.1 and 7.7 at rat and human VR1 receptors respectively). Also blocks anandamide uptake (IC 50 = 9 μ M) and may bind to CB 1 cannabinoid receptors. Antinociceptive following systemic administration. Also available as part of the Vanilloid TRPV1 Receptor Tocriset™ .

Desiccate at -20°C

[1] JOHN M. JANUSZ. Vanilloids. 1. Analogs of capsaicin with antinociceptive and antiinflammatory activity[J]. Journal of Medicinal Chemistry, 1993, 36 18: 2595-2604. DOI: 10.1021/jm00070a002
[2] VINCENZO DI MARZO . Interactions between synthetic vanilloids and the endogenous cannabinoid system[J]. FEBS Letters, 1998, 436 3: Pages 449-454. DOI: 10.1016/s0014-5793(98)01175-2