| Identification | Back Directory | [Name]
4-[(1R,6R)-3-METHYL-6-(1-METHYLETHENYL)-2-CYCLOHEXEN-1-YL]-5-PENTYL-1,3-BENZENEDIOL | [CAS]
22972-55-0 | [Synonyms]
ABN-CBD
Abn CBD,AbnCBD
Cannabidiol, Abnormal
1-Hydroxy-3-n-Pentylcannabidiol
Abn-CBD
(Abnormal Cannabidiol)
4-(p-Mentha-1,8-dien-3-yl)-5-pentylresorcinol
8-dien-3-yl-5-pentyl-4-p-mentha-(-)-(e)-resorcino
(e)-(-)-4-p-mentha-1,8-dien-3-yl-5-pentylresorcinol
Resorcinol, 4-p-mentha-1,8-dien-3-yl-5-pentyl-, (-)-(E)-
4-[(1R,6R)-3-METHYL-6-(1-METHYLETHENYL)-2-CYCLOHEXEN-1-YL]-5-PENTYL-1,3-BENZENEDIOL | [Molecular Formula]
C21H30O2 | [MDL Number]
MFCD08705633 | [MOL File]
22972-55-0.mol | [Molecular Weight]
314.46 |
| Chemical Properties | Back Directory | [Boiling point ]
446.4±45.0 °C(Predicted) | [density ]
1.025±0.06 g/cm3(Predicted) | [storage temp. ]
Desiccate at -20°C | [solubility ]
Soluble in methyl acetate (supplied pre-dissolved - 5mg/ml) | [form ]
Powder | [pka]
9.94±0.45(Predicted) |
| Hazard Information | Back Directory | [Description]
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. | [Uses]
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. | [Biological Activity]
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. | [storage]
Desiccate at -20°C | [References]
[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 |
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