20675-51-8

Usage

Uses

Used in Pharmaceutical Research:
Cannabichromene is used as a research compound for pharmaceutical development due to its anti-inflammatory, antimicrobial, and analgesic properties. It can be utilized in the creation of new drugs targeting various medical conditions, such as pain management and inflammation-related disorders.
Used in Cannabis Potency Testing:
Cannabichromene is used as a quantitative standard for Cannabis potency testing. It helps in determining the concentration of cannabinoids in Cannabis products, ensuring their quality and safety for consumers.
Used in Impurity Profiling:
Cannabichromene is used as a reference material for impurity profiling in the Cannabis industry. It aids in identifying and quantifying impurities in Cannabis products, which is crucial for maintaining product quality and safety.
Used in Forensic Analysis:
Cannabichromene is used as a forensic tool in the analysis of Cannabis samples. It helps in the identification and quantification of cannabinoids in legal and criminal investigations, contributing to the enforcement of drug laws and regulations.
Used in Antimicrobial Applications:
Cannabichromene is used as an antimicrobial agent, particularly against various bacterial and fungal infections. Its antimicrobial properties make it a potential candidate for the development of new antibiotics and antifungal medications.
Used in Pain Management:
Cannabichromene is used as an analgesic agent for pain management. Its ability to alleviate pain without causing psychoactive effects makes it a promising alternative to traditional pain-relieving medications.
Used in Inflammation Treatment:
Cannabichromene is used as an anti-inflammatory agent for the treatment of various inflammation-related conditions, such as arthritis, allergies, and autoimmune disorders. Its anti-inflammatory properties can help reduce inflammation and alleviate associated symptoms.

Safety Profile

Poison by intravenous and intraperitoneal routes. Experimental reproductive effects. Mutation data reported. Whenheated to decomposition it emits acrid smoke and irritating fumes

InChI:InChI=1/C21H30O2/c1-5-6-7-10-17-14-19(22)18-11-13-21(4,23-20(18)15-17)12-8-9-16(2)3/h9,11,13-15,22H,5-8,10,12H2,1-4H3

Upstream product

• 141-27-5 3,7-dimethyl-2,6-octadienal 
• 500-66-3 Olivetol 
• 20408-52-0 6-carboxy-2-methyl-2-(4-methylpent-3-enyl)-7-pentylchromen-5-ol 
• 25654-31-3 2-[(2E)-3,7-dimethylocta-2,6-dienyl]-5-pentyl-benzene-1,3-diol 
• 75-64-9 tert-butylamine 
• 5392-40-5 (E/Z)-3,7-dimethyl-2,6-octadienal 
• 106-24-1 Geraniol 
• 13956-29-1 CBD 
• 22976-40-5 1,3-dimethoxy-5-pentylbenzene 
• 110-53-2 1-Bromopentane 
• 20469-65-2 1-bromo-3,5-dimethoxybenzene 
• 855875-40-0 2,4-dihydroxyl-6-pentylbenzaldehyde 
• 112639-01-7 2-bromo-1,5-dimethoxy-3-pentyl-benzene 
• 162330-79-2 methyl 5-methoxy-2-methyl-7-pentyl-2H-chromen-2-acetate 

Downstream Products

• 21366-63-2 cannabicyclol 
• 19352-64-8 cannabicitran 
• 521-35-7 cannabinol 

Relevant academic research and scientific papers

Constituents of Cannabis sativa L. An improved method for the synthesis of dl-cannabichromene

A new procedure was developed for the synthesis of cannabichromene (III) which involves reflux of equimolar amounts of olivetol (I), citral (II) and t-butylamine in toluene for 9 hours. The purification of III was best achieved by sodium borohydride reduction of unreacted II followed by column chromatography on 1% sodium hydroxide impregnated silica gel 60-PF. The yield of III (62.0%) was much higher than that reported in the literature.

Synthesis of Cannabinoids: "in Water" and "on Water" Approaches: Influence of SDS Micelles

We have proven that the biomimetic-like synthesis of cannabinoids from citral and the corresponding phenolic counterpart may well be carried out using water as a solvent. The influence of different additives such as surfactants was also analyzed. Rationalization of the reaction mode and regiochemistry of the processes were provided in terms of "on water"and "in water"reactions. The same reactions were conducted in organic media using Ga(III) salts as catalysts. Worthy of being underlined, an unprecedented formal [2+2+2] process was found to occur between two citral molecules and the corresponding phenolic species in both aqueous and organic environments. Computational studies were performed in order to gain a comprehensive mechanistic and energetic understanding of the different steps of this singular process. Finally, the influence of SDS micelles in the chemical behavior of olivetol and citral was also pursued using PGSE diffusion and NOESY NMR studies. These data permitted to tentatively propose the existence of a mixed micelle between olivetol and SDS assemblies.

Cannabichromene is a cannabinoid CB2 receptor agonist

Background and Purpose: Cannabichromene (CBC) is one of the most abundant phytocannabinoids in Cannabis spp. It has modest antinociceptive and anti-inflammatory effects and potentiates some effects of Δ9-tetrahydrocannabinol in vivo. How CBC exerts these effects is poorly defined and there is little information about its efficacy at cannabinoid receptors. We sought to determine the functional activity of CBC at cannabinoid CB1 and CB2 receptors. Experimental Approach: AtT20 cells stably expressing haemagglutinin-tagged human CB1 and CB2 receptors were used. Assays of cellular membrane potential and loss of cell surface receptors were performed. Key Results: CBC activated CB2 but not CB1 receptors to produce hyperpolarization of AtT20 cells. This activation was inhibited by a CB2 receptor antagonist AM630, and sensitive to Pertussis toxin. Application of CBC reduced activation of CB2, but not CB1, receptors by subsequent co-application of CP55,940, an efficacious CB1 and CB2 receptor agonist. Continuous CBC application induced loss of cell surface CB2 receptors and desensitization of the CB2 receptor-induced hyperpolarization. Conclusions and Implications: CBC is a selective CB2 receptor agonist displaying higher efficacy than tetrahydrocannabinol in hyperpolarizing AtT20 cells. CBC can also recruit CB2 receptor regulatory mechanisms. CBC may contribute to the potential therapeutic effectiveness of some cannabis preparations, potentially through CB2 receptor-mediated modulation of inflammation.

Total syntheses of cannabicyclol, clusiacyclol A and B, iso-eriobrucinol A and B, and eriobrucinol

Total syntheses of a series of chromane natural products that contain a cyclobutane ring are described. A unified theme in the strategy employed for all these syntheses is an oxa-[3 + 3] annulation for constructing the chromane nucleus and a stepwise cationic [2 + 2] cycloaddition for the cyclobutane formation. More importantly, the two reactions could be rendered in tandem, thereby providing an expeditious approach to this family of natural products.

A Total Synthesis of (±)-Rhododaurichromanic Acid A via an Oxa-[3+3] Annulation of Resorcinols

Development of an oxa-[3+3] annulation of vinyliminium salts with resorcinols as a 1,3-diketo equivalent is described. This annulation constitutes a cascade of Knoevenagel condensation-oxa-electrocyclization leading to a direct access to chromenes. A series of attempts was made to demonstrate its synthetic utility in natural product synthesis, culminating in a total synthesis of (±)-rhododaurichromanic acid A that also featured an intramolecular Gassman-type cationic [2+2] cycloaddition.

Antioxidant function of phytocannabinoids: Molecular basis of their stability and cytoprotective properties under UV-irradiation

In this contribution, a comprehensive study of the redox transformation, electronic structure, stability and photoprotective properties of phytocannabinoids is presented. The non-psychotropic cannabidiol (CBD), cannabigerol (CBG), cannabinol (CBN), cannabichromene (CBC), and psychotropic tetrahydrocannabinol (THC) isomers and iso-THC were included in the study. The results show that under aqueous ambient conditions at pH 7.4, non-psychotropic cannabinoids are slight or moderate electron-donors and they are relatively stable, in the following order: CBD > CBG ≥ CBN > CBC. In contrast, psychotropic Δ9-THC degrades approximately one order of magnitude faster than CBD. The degradation (oxidation) is associated with the transformation of OH groups and changes in the double-bond system of the investigated molecules. The satisfactory stability of cannabinoids is associated with the fact that their OH groups are fully protonated at pH 7.4 (pKa is ≥ 9). The instability of CBN and CBC was accelerated after exposure to UVA radiation, with CBD (or CBG) being stable for up to 24 h. To support their topical applications, an in vitro dermatological comparative study of cytotoxic, phototoxic and UVA or UVB photoprotective effects using normal human dermal fibroblasts (NHDF) and keratinocytes (HaCaT) was done. NHDF are approx. twice as sensitive to the cannabinoids’ toxicity as HaCaT. Specifically, toxicity IC50 values for CBD after 24 h of incubation are 7.1 and 12.8 μM for NHDF and HaCaT, respectively. None of the studied cannabinoids were phototoxic. Extensive testing has shown that CBD is the most effective protectant against UVA radiation of the studied cannabinoids. For UVB radiation, CBN was the most effective. The results acquired could be used for further redox biology studies on phytocannabinoids and evaluations of their mechanism of action at the molecular level. Furthermore, the UVA and UVB photoprotectivity of phytocannabinoids could also be utilized in the development of new cannabinoid-based topical preparations.

CANNABICHROMENE COMPOSITIONS AND METHODS OF SYNTHESIZING CANNABICHROMENE

Compositions having enhanced cannabichromene (CBC) and abnormal cannabichromene (CBCab) concentrations are disclosed herein as are methods of synthesizing CBC and CBCab. Relative to conventional methods, the methods of the present disclosure may: (i) be better suited to large-scale conditions in that they do not require dangerous and/or toxic solvents and/or reagents; (ii) provide product mixtures with enhanced CBCab concentrations; (iii) provide CBC at higher yield; (iv) provide easier to purify product mixtures comprising CBC; (v) provide product mixtures that comprise unique ratios of CBCab relative to other cannabinoids; and/or (vi) provide product mixtures with reduced THC concentrations.

Cannabichromene, Related Phytocannabinoids, and 5-Fluoro-cannabichromene Have Anticonvulsant Properties in a Mouse Model of Dravet Syndrome

Cannabis-based products are increasingly being used to treat refractory childhood epilepsies such as Dravet syndrome. Cannabis contains at least 140 terpenophenolic compounds known as phytocannabinoids. These include the known anticonvulsant compound cannabidiol (CBD) and several molecules showing emergent anticonvulsant properties in animal models. Cannabichromene (CBC) is a phytocannabinoid frequently detected in artisanal cannabis oils used in the community by childhood epilepsy patients. Here we examined the brain and plasma pharmacokinetic profiles of CBC, cannabichromenic acid (CBCA), cannabichromevarin (CBCV), and cannabichromevarinic acid (CBCVA) following intraperitoneal administration in mice. The anticonvulsant potential of each was then tested against hyperthermia-induced seizures in the Scn1a+/- mouse model of Dravet syndrome. All phytocannabinoids within the CBC series were readily absorbed and showed substantial brain penetration (brain-plasma ratios ranging from 0.2 to 5.8). Anticonvulsant efficacy was evident with CBC, CBCA, and CBCVA, each significantly increasing the temperature threshold at which Scn1a+/- mice had a generalized tonic-clonic seizure. We synthesized a fluorinated derivative of CBC (5-fluoro-CBC), which showed improved brain penetration relative to the parent CBC molecule but not any greater anticonvulsant effect. Since CBC and derivatives are anticonvulsant in a model of intractable pediatric epilepsy, they may constitute part of the mechanism through which artisanal cannabis oils are anticonvulsant in patients.

METHODS OF SYNTHESIZING HIGH-PURITY CANNABICYCLOL AND ARTIFICIAL RESINS COMPRISING CANNABICYCLOL

Compositions having enhanced cannabicyclol (CBL) or CBL derivative concentrations are disclosed herein as are methods of synthesizing CBL and CBL derivative in high-purity form. Relative to conventional methods, the methods of the present disclosure may: (i) be better suited to large-scale conditions in that they do not require dangerous and/or toxic solvents and/or reagents; (ii) be more tolerant of complex starting compositions, such as cannabinoid extracts, isolates and/or distillates; (iii) provide CBL and/or CBL derivative at higher yield; (iv) provide easier methods to purify product mixtures comprising CBL and/or CBL derivative; (v) provide product mixtures that comprise unique ratios of CBL or CBL derivative relative to other cannabinoids; (vi) provide product mixtures with reduced THC concentrations and/or (vii) provide artificial resins having of a mixture cannabinoids that cannot be produced by extracting cannabis plant material.

PREPARING AND MODIFYING MEROTERPENE POLYKETIDES, KETONES, AND LACTONES FOR CANNABINOID SEMISYNTHESIS

Provided herein are processes, including semi-synthetic, and synthetic processes for preparing cannabinoids, and cannabinoid compositions provided thereby.