-Cannabichromene.svg) | |
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| Names | |
|---|---|
| IUPAC name 2-Methyl-2-(4-methylpent-3-enyl)-7-pentyl-5-chromenol | |
| Identifiers | |
3D model (JSmol) | |
| ChEMBL | |
| ChemSpider |
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| ECHA InfoCard | 100.236.929 |
| UNII | |
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| Properties | |
| C21H30O2 | |
| Molar mass | 314.469 g·mol−1 |
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa). | |
Cannabichromene (CBC), also called cannabichrome, cannanbichromene, pentylcannabichromene or cannabinochromene,[1] is aphytocannabinoid, one of the hundreds ofcannabinoids found in theCannabis plant.[2] It bears structural similarity to the other natural cannabinoids, includingtetrahydrocannabinol (THC),tetrahydrocannabivarin (THCV),cannabidiol (CBD), andcannabinol (CBN), among others.[2][3] It is not scheduled by theConvention on Psychotropic Substances.
Within theCannabis plant, CBC occurs mainly ascannabichromenic acid (CBCA, 2-COOH-CBC, CBC-COOH).Geranyl pyrophosphate andolivetolic acid combine to producecannabigerolic acid (CBGA; the sole intermediate for all other phytocannabinoids), which is cyclized by the enzyme CBCA synthase to form CBCA. Over time, or when heated above 93 °C, CBCA isdecarboxylated, producing CBC. See also the biosynthetic scheme image below.[citation needed]
Cannabichromene has been hypothesized to affect THC psychoactivity, thoughin vivo effects have not been demonstrated.[4] CBC acts on theTRPV1 andTRPA1 receptors, interfering with their ability to break down endocannabinoids (chemicals such asanandamide and2-AG that the body creates naturally).[5][unreliable source?] CBC has shown antitumor effects in breast cancer xenoplants in mice.[6] It also hasanticonvulsant activity in amouse model.[7]
In vitro, CBC binds weakly toCB1 andCB2 with binding affinities of 713 nM and 256 nM, respectively, which are significantly lower than that forTHC with 35 nM at CB1.[8][9] acting as an agonist forcAMP stimulation and an antagonist atbeta-arrestin.[8] Additionally, CBC is an agonist ofTRPA1, and less potentlyTRPV3 andTRPV4.[2] CBC has twostereoisomers.
