1242-67-7

Usage

Uses

Used in Pharmaceutical Industry:
Cannabidiol dimethyl ether is used as an inhibitor of 15-lipoxygenase for its potential therapeutic effects in treating inflammation, thrombosis, and cancer. Its selective inhibition of 15-LO with an IC50 value of 0.28 μM makes it a promising candidate for the development of new drugs targeting these conditions.
Used in Anti-inflammatory Applications:
Cannabidiol dimethyl ether is used as an anti-inflammatory agent, as it inhibits the production of unsaturated fatty acid hydroperoxides, which act as mediators in inflammation. This makes it a potential treatment for various inflammatory disorders.
Used in Antithrombotic Applications:
Cannabidiol dimethyl ether is used as an antithrombotic agent, as it can potentially reduce the formation of blood clots by inhibiting the activity of 15-LO, which is involved in the clotting process.
Used in Anticancer Applications:
Cannabidiol dimethyl ether is used as an anticancer agent, as it can potentially inhibit the growth and progression of cancer cells by targeting the 15-LO pathway. Its selective inhibition of 15-LO may also reduce the side effects associated with conventional chemotherapy drugs.

Biological Activity

cannabidiol dimethyl ether (cbdd) is a cannabidiol derivative that potently and selectively inhibits 15-lox with an ic50 value of 0.28 μm.15-lox can oxygenate cholesterol esters in the low-density lipoprotein (ldl) particle. thus, 15-lox has been involved in the development of atherosclerosis, and cbdd may be a useful prototype for producing medicines for atherosclerosis [1].cbdd showed a potent inhibitory effect on the catalytic activity of cytochrome p450 2c19 with an ic50 value of 14.8 μμ [2]. cbdd inhibited the cyp2b6 activity with the ic50values of 75.7 μm [3]. cytochrome p450 enzymes have been isolated from numerous mammalian tissues such as liver, kidney, lung, intestine, adrenal cortex. cytochrome p450 enzymes have also existed in insects, plants, yeasts, and bacteria. cytochrome p450 has been known to catalyze hydroxylations, epoxidations, n-, s-, and o-dealkylations, n-oxidations, sulfoxidations, dehalogenations, and other reactions [4].

references

[1] takeda s, usami n, yamamoto i, et al. cannabidiol-2′, 6′-dimethyl ether, a cannabidiol derivative, is a highly potent and selective 15-lipoxygenase inhibitor[j]. drug metabolism and disposition, 2009, 37(8): 1733-1737.[2] jiang r, yamaori s, okamoto y, et al. cannabidiol is a potent inhibitor of the catalytic activity of cytochrome p450 2c19[j]. drug metabolism and pharmacokinetics, 2013, 28(4): 332-338.[3] yamaori s, maeda c, yamamoto i, et al. differential inhibition of human cytochrome p450 2a6 and 2b6 by major phytocannabinoids[j]. forensic toxicology, 2011, 29(2): 117-124.[4] groves j t, han y z. models and mechanisms of cytochrome p450 action[m]//cytochrome p450. springer us, 1995: 3-48.

InChI:InChI=1/C21H30O2.C2H6O/c1-5-6-7-8-16-12-19(22)21(20(23)13-16)18-11-15(4)9-10-17(18)14(2)3;1-3-2/h11-13,17-18,22-23H,2,5-10H2,1,3-4H3;1-2H3/t17-,18+;/m0./s1

Upstream product

• 13956-29-1 CBD 
• 74-88-4 methyl iodide 
• 22976-40-5 1,3-dimethoxy-5-pentylbenzene 
• 78340-84-8 (1S,4R)-p-mentha-2,8-dien-1-yl acetate 
• 67-56-1 methanol 
• 10293-10-4 3-endo-9-dibromo-1,7,7-trimethylbicyclo<2.2.1>heptan-2-one 
• 67895-00-5 (2,6-dimethoxy-4-pentylphenyl)lithium 
• 140633-50-7 (1R,2S,3R,4R,7R)-7-Bromomethyl-3-(2,6-dimethoxy-4-pentyl-phenyl)-1,7-dimethyl-bicyclo[2.2.1]heptan-2-ol 
• 140633-46-1 endo-9-Bromo-3-(2,6-dimethoxy-4-n-pentylphenyl)camphor 
• 3410-84-2 2,6-dimethoxy-4-pentylbenzaldehyde 
• 3411-09-4 2.6-Dimethoxy-4-pentyl-benzalaceton 
• 1310045-84-1 1-(2',6'-dimethoxy-5-methyl-4'-pentyl-1,2,3,4-tetrahydro-[1,1'-biphenyl]-2-yl)ethanone 
• 27200-84-6 methyl triphenylphosphonium bromide 
• 63953-83-3 2,4-dimethoxy-6-pentylbenzoic acid methyl ester 

Downstream Products

• 1242-66-6 (1R)-1r-Methyl-4t-isopropyl-3c-(2,6-dimethoxy-4-pentyl-phenyl)-cyclohexan 
• 129333-58-0 5-[4-((1R,6R)-6-Isopropenyl-3-methyl-cyclohex-2-enyl)-3,5-dimethoxy-phenyl]-pentan-2-ol 
• 129333-59-1 (4R,5R)-4-(2,6-Dimethoxy-4-pentyl-phenyl)-5-isopropenyl-2-methyl-cyclohex-2-enol 
• 129354-34-3 1,2-oxido-dimethoxy-hexahydrocannabinol 
• 88510-93-4 2-[(1R,2R,5S)-5-Bromo-2-(1-bromo-1-methyl-ethyl)-5-methyl-cyclohexyl]-1,3-dimethoxy-5-pentyl-benzene 
• 380495-68-1 (3R,4R)-3-[2,6-dihydroxy-4-pentylphenyl]-2-hydroxy-4-isopropenyl-1-methylenecyclohexane 
• 380495-74-9 Acetic acid 3-acetoxy-2-((1R,6R)-3-formyl-6-isopropenyl-cyclohex-2-enyl)-5-pentyl-phenyl ester 
• 380495-72-7 Acetic acid 3-acetoxy-2-((1R,6R)-3-bromomethyl-6-isopropenyl-cyclohex-2-enyl)-5-pentyl-phenyl ester 
• 380599-35-9 (3R,4R)-3-(2,6-Diacetoxy-4-pentyl-phenyl)-4-isopropenyl-cyclohex-1-enecarboxylic acid 
• 380495-70-5 (3R,4R)-3-[2,6-diacetoxy-4-pentylphenyl]-2-acetoxy-4-isopropenyl-1-methylenecyclohexane 
• 306734-02-1 7-bromo-dimethoxycannabidiol 
• 27179-28-8 (+/-)-delta7-Tetrahydrocannabinol 
• 1972-08-3 dronabinol 
• 1972-05-0 Cannabidiol monomethyl ether 

Relevant academic research and scientific papers

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.

Investigation of Chocolate Matrix Interference on Cannabinoid Analytes

The first known findings of chocolate matrix interference on cannabinoid analytes is reported. Stock solutions of four biogenic cannabinoids (Δ9-tetrahydrocannabinol, cannabidiol, cannabinol, and cannabigerol) and one synthetic cannabinoid (cannabidiol di

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.

Synthetic method of cannabidiol

The invention belongs to the field of chemical pharmacy, and particularly discloses a synthetic method of cannabidiol. The synthetic method comprises the following steps: S1, adopting 2, 4-dimethoxy-6-amyl methyl benzoate as a raw material, and carrying out a coupling reaction on the raw material and (1S, 4R)-1-methyl-4-(1-methylvinyl)-2-cyclohexene-1-ol under a Lewis acid catalysis condition to obtain an intermediate (I); S2, performing high-temperature decarboxylation on the prepared intermediate (I) under the action of strong alkali to prepare an intermediate (II); and S3, removing methyl from the prepared intermediate (II) under the action of boron tribromide to obtain the final product cannabidiol. The purity of the cannabidiol obtained by the preparation method disclosed by the invention is 99.90-99.99%; the total yield of the finally prepared bulk drug with qualified purity can reach 60-80% at most, the process is obviously improved, and the method has a good industrial application prospect.

SYNTHESIS OF CANNABINOIDS

Provided are synthesis processes and intermediates for preparing cannabinoids and analogs.

Enantioselective Total Synthesis of Cannabinoids - A Route for Analogue Development

A practical synthetic approach to Δ9-tetrahydrocannabinol (1) and cannabidiol (2) that provides scalable access to these natural products and should enable the generation of novel synthetic analogues is reported.

Synthesis of cannabidiols via alkenylation of cyclohexenyl monoacetate

Because of the lack of potency binding to the receptors responsible for psychoactivity, cannabidiol has received much attention as a lead compound to develop a nonpsychotropic drug. Herein, we establish a method to access not only cannabidiol but also its analogues. The key reaction is nickel-catalyzed allylation of 2-cyclohexene-1,4-diol monoacetate with a new reagent, (alkenyl)ZnCl/TMEDA, which gives a SN2-type product with 94% regioselectivity in good yield.

Enantiomeric cannabidiol derivatives: Synthesis and binding to cannabinoid receptors

(-)-Cannabidiol (CBD) is a major, non psychotropic constituent of cannabis. It has been shown to cause numerous physiological effects of therapeutic importance. We have reported that CBD derivatives in both enantiomeric series are of pharmaceutical interest. Here we describe the syntheses of the major CBD metabolites, (-)-7-hydroxy-CBD and (-)-CBD-7-oic acid and their dimethylheptyl (DMH) homologs, as well as of the corresponding compounds in the enantiomeric (+)-CBD series. The starting materials were the respective CBD enantiomers and their DMH homologs. The binding of these compounds to the CB1 and CB2 cannabinoid receptors are compared. Surprisingly, contrary to the compounds in the (-) series, which do not bind to the receptors, most of the derivatives in the (+) series bind to the CB1 receptor in the low nanomole range. Some of these compounds also bind weakly to the CB2 receptor. The Royal Society of Chemistry 2005.

Synthesis of a primary metabolite of cannabidiol

(matrix presented) Cannabidiol 1 is the major nonpsychotropic, neutral constituent in most cannabis preparations. It is devoid of the psychoactive properties typical of cannabis; however, it produces numerous, potentially therapeutic pharmacological effec

A One-Step Method for the α-Arylation of Camphor. Synthesis of (-)-Cannabidiol and (-)-Cannabidiol Dimethyl Ether

The syntheses of (-)-cannabidiol and (-)-cannabidiol dimethyl ether were accomplished via fragmentation of an appropriately substituted 9-bromocamphor derivative.A new method of α-arylation of 3,9-dibromocamphor was shown to provide a variety of α-arylated camphor derivatives in good yields.