Abn-cbd

Base Information

• Chemical Name: Abn-cbd
• CAS No.: 22972-55-0
• Molecular Formula: C21H30 O2
• Molecular Weight: 314.468
• UNII: T4WF2D7YPH
• DSSTox Substance ID: DTXSID10945675
• Nikkaji Number: J1.975.652A
• Wikipedia: Abnormal_cannabidiol
• Wikidata: Q27074295
• Pharos Ligand ID: 6DNNCKNYQQA4
• ChEMBL ID: CHEMBL499876
• Mol file: 22972-55-0.mol

Synonyms:4-(3-3,4-p-menthadien-(1,8)-yl)olivetol;abn-cbd;abnormal cannabidiol

Chemical Property of Abn-cbd

Chemical Property:

• Appearance/Colour: Amber oil
• Vapor Pressure: 1.39E-08mmHg at 25°C
• Refractive Index: 1.545
• Boiling Point: 446.4 °C at 760 mmHg
• Flash Point: 196.7 °C
• PSA: 40.46000
• Density: 1.025 g/cm³
• LogP: 5.84650
• Storage Temp.: Desiccate at -20°C
• XLogP3: 6.5
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 6
• Exact Mass: 314.224580195
• Heavy Atom Count: 23
• Complexity: 426

Purity/Quality:

98%Min ^*data from raw suppliers

Abn-CBD ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCCC1=C(C(=CC(=C1)O)O)C2C=C(CCC2C(=C)C)C
• Isomeric SMILES: CCCCCC1=C(C(=CC(=C1)O)O)[C@@H]2C=C(CC[C@H]2C(=C)C)C
• 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.

Technology Process of Abn-cbd

There total 21 articles about Abn-cbd which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 55.0%

(+)-cis-piperityl acetate + Olivetol (500-66-3) → CBD (13956-29-1,521-37-9) + abnormal cannabidiol (22972-55-0) + (-)-2,4-Bis-<3,4-trans-p-menthadien-(1,8)-yl-(3)>-olivetol (22972-53-8)

Guidance literature:

With boron trifluoride diethyl etherate; In dichloromethane; for 0.116667h; Flow reactor;

DOI:10.1002/ejoc.202001633

Reference yield: 52.0%

cis-para-mentha-2,8-diene-1-ol + Olivetol (500-66-3) → CBD (13956-29-1,521-37-9) + abnormal cannabidiol (22972-55-0)

Guidance literature:

MoCl₂(acetylacetonate)2; silver trifluoromethanesulfonate; In dichloromethane; at -20 ℃; for 3h;

DOI:10.1135/cccc20011257

Reference yield: 14.0%

(1S,4R)-p-mentha-2,8-dien-1-ol (22972-51-6) + Olivetol (500-66-3) → CBD (13956-29-1,521-37-9) + abnormal cannabidiol (22972-55-0) + (-)-2,4-Bis-<3,4-trans-p-menthadien-(1,8)-yl-(3)>-olivetol (22972-53-8)

Guidance literature:

With aluminum oxide; boron trifluoride diethyl etherate; In dichloromethane; at 40 - 41 ℃; for 0.00277778h;

DOI:10.1016/S0040-4039(00)98518-6

upstream raw materials:

(1S,4R)-p-mentha-2,8-dien-1-ol

Olivetol

(1S,2S,3R,6R)-(+)-trans-car-2-ene epoxide

3-carene epoxide