4-[(1R,6R)-3-Methyl-6-(1-methylethenyl)-2-cyclohexen-1-yl]-5-pentyl-1,3-benzenediol

Abnormal cannabidiol is a synthetic cannabidiol agonist of GPR55 (EC₅₀ = 2.5 μM in a GTPγS binding assay). It is selective for GPR55 over cannabinoid (CB) receptor 1 (CB₁) and CB₂ (EC₅₀s = >30 μM for both in GTPγS binding assays). It is also a full agonist at GPR18, with an EC₅₀ value of 0.835 μM for inducing p44/42 MAPK phosphorylation in HEK293 cells expressing GPR18. Abnormal cannabidiol increases migration of BV-2 microglial cells (EC₅₀ = 0.6 μM). It induces endothelium-dependent vasodilation via a CB₁-CB₂-NO-independent mechanism and inhibits vasoconstriction induced by endothelin 1 (ET-1; ) in retinal arterioles, an effect that can be blocked by the calcium-sensitive potassium channel blocker apamin . Abnormal cannabidiol also decreases blood pressure in anesthetized rats when administered intravenously at a dose of 20 μg/g or when administered directly into the rostral ventrolateral medulla at 0.4 and 0.8 μg.

Abnormal Cannabidiol is a potent and selective GPR55 agonist.Abnormal cannabidiol (Abn-CBD) is a synthetic regioisomer of cannabidiol, which unlike most other cannabinoids produces vasodilator effects, lowers blood pressure, and induces cell migration, cell proliferation and mitogen-activated protein kinase activation in microglia, but without producing any psychoactive effects.

Neurobehaviorally inactive cannabinoid that acts as a selective agonist for GPR55 (EC 50 values are 2.5, >30 and >30 μ M at GPR55, CB 1 and CB 2 receptors respectively). Increases phosphorylation of protein kinases in, and migration of, human umbilical vein endothelial cells.

Desiccate at -20°C

[1] DR. ELENA CHIURCHIù . A Novel and Practical Continuous Flow Chemical Synthesis of Cannabidiol (CBD) and its CBDV and CBDB Analogues[J]. European Journal of Organic Chemistry, 2021, 2021 8: Pages 1286-1289. DOI: 10.1002/ejoc.202001633
[2] LIGUO SONG. Development of a validated method for rapid quantification of up to sixteen cannabinoids using ultra-high-performance liquid chromatography diode-array detector with optional electrospray ionization time-of-flight mass spectrometry detection[J]. Journal of Chromatography A, 2022, 1670: Article 462953. DOI: 10.1016/j.chroma.2022.462953