35482-50-9

Usage

Biological Activity

o-1821 is an cannabidiol analog with similar structure to o-1918, a selective antagonist of abnormal cannabidiol.abnormal cannabidiol, a synthetic regioisomer of cannabidiol, fails to elicit either central cannabinoid (cb1) or peripheral cannabinoid (cb2) receptors and is lack of psychotropic activity. it can induce endothelium-dependent vasodilation through a cb1/cb2/nitric oxide-independent mechanism.

in vitro

o-1821 is a cannabidiol analog with similar structure to o-1918, which was identified as a selective antagonist of abnormal cannabidiol at the non-central cannabinoid (cb1)/peripheral cannabinoid (cb2) receptors endothelial receptor. it was found that o-1918 could not bind to cb1 or cb2 receptors and thus could not cause vasorelaxation at concentrations up to 30 μm, but it could cause concentration-dependent inhibition of the vasorelaxant effects of abn-cbd and anandamide. moreover, in human umbilical vein endothelial cells, abn-cbd was able to induce phosphorylation of p42/44 mitogenactivated protein kinase and protein kinase b/akt, which could be inhibited by o-1918 or by phosphatidylinositol 3 (pi3) kinase inhibitors [1].

in vivo

o-1918 was found to be able to inhibit the hypotensive effect of abn-cbd dose-dependently but not the hypotensive effect of the cb1 receptor agonist (-)-11-oh-δ9-tetrahydrocannabinol dimethylheptyl in anesthetized mice [1].

references

[1] offertáler, l. ,mo, f.m.,bátkai, s., et al. selective ligands and cellular effectors of a g protein-coupled endothelial cannabinoid receptor. molecular pharmacology 63(3), 699-705 (2003).

Upstream product

• 504-15-4 orcinol 
• 22972-51-6 (1S,4R)-p-mentha-2,8-dien-1-ol 
• 108-73-6 3,5-dihydroxyphenol 
• 75-16-1 methylmagnesium bromide 
• 715-33-3 methyl 2,4-dihydroxy-3,5-dibromo-6-methylbenzoate 
• 63953-78-6 Methyl-cannabidiorcolat 
• 6909-30-4 (1S,2R,4R)-limonene-1,2-epoxide 
• 34837-55-3 Phenylselenyl bromide 
• 74756-09-5 (1S,2S,4R)-4-Isopropenyl-1-methyl-2-phenylselanyl-cyclohexanol 

Downstream Products

• 536697-79-7 O-1918 
• 728044-69-7 delta-9-tetrahydrocannabiorcol 

Relevant academic research and scientific papers

Stereoselective Synthesis of Nonpsychotic Natural Cannabidiol and Its Unnatural/Terpenyl/Tail-Modified Analogues

Here, we report a three-step concise and stereoselective synthesis route to one of the most important phytocannabinoids, namely, (-)-cannabidiol (-CBD), from inexpensive and readily available starting material R-(+)-limonene. The synthesis involved the diastereoselective bifunctionalization of limonene, followed by effective elimination leading to the generation of key chiral p-mentha-2,8-dien-1-ol. The chiral p-mentha-2,8-dien-1-ol on coupling with olivetol under silver catalysis provided regiospecific (-)-CBD, contrary to reported ones which gave a mixture. The newly developed approach was further extended to its structural analogues cannabidiorcin and other tail/terpenyl-modified analogues. Moreover, its opposite isomer (+)-cannabidiol was also successfully synthesized from S-(-)-limonene.

CANNABIDIOL-TYPE CANNABINOID COMPOUND

The present invention relates to a cannabidiol (CBD) type cannabinoid compound for use as a medicament. The CBD-type cannabinoid, cannabidiol-C1 (CBD-C1), is a naturally occurring cannabinoid that can be found in minor quantities in the cannabis plant. Furthermore, the 5 cannabinoid can be produced by synthetic means and a method for the production of CBD-C1 is described herein. In addition, disclosed herein are data which demonstrate the efficacy of CBD-C1 in models of disease.

Synthesis of CBD and Its Derivatives Bearing Various C4′-Side Chains with a Late-Stage Diversification Method

A novel synthetic route for making (-)-CBD and its derivatives bearing various C4′-side chains is developed by a late-stage diversification method. Starting from commercially available phloroglucinol, the key intermediate (-)-CBD-2OPiv-OTf is efficiently and regioselectively prepared and further undergoes Negishi cross-coupling to furnish (-)-CBD. This approach allowed an efficient synthesis of (-)-CBD in a five-step total 52% yield on a 10 g scale. Furthermore, diversification on the C4′-side chain with this method can be realized in a wide range.

CATALYTIC CANNABINOID PROCESSES AND PRECURSORS

The present disclosure relates to new cannabinoid sulfonate esters and processes for their use to prepare cannabinoids. The disclosure also relates to the use of catalysts and catalytic processes for the preparation of cannabinoids from the cannabinoid sulfonate esters.

BORON TRIFLUORIDE ETHERATE ON ALUMINA - A MODIFIED LEWIS ACID REAGENT. AN IMPROVED SYNTHESIS OF CANNABIDIOL.

Boron trifluoride etherate on alumina catalyses the condensation of resorcinols and monomethyl resorcinols with several monoterpenoid allylic alcohols: in contrast to paralell reactions with boron trifluoride etherate in solution the products obtained do not undergo further cyclisations.