Cannabichromene
Chemical compound
From Wikipedia, the free encyclopedia
Cannabichromene (CBC), also called cannabichrome, cannanbichromene, pentylcannabichromene or cannabinochromene,[1] is a phytocannabinoid, one of the hundreds of cannabinoids found in the Cannabis plant.[2] It bears structural similarity to the other natural cannabinoids, including tetrahydrocannabinol (THC), tetrahydrocannabivarin (THCV), cannabidiol (CBD), and cannabinol (CBN), among others.[2][3] It is not scheduled by the Convention on Psychotropic Substances.
-Cannabichromene.svg)
| |
 | |
| Names | |
|---|---|
| IUPAC name
2-Methyl-2-(4-methylpent-3-enyl)-7-pentyl-5-chromenol | |
| Identifiers | |
3D model (JSmol) |
|
| ChEMBL | |
| ChemSpider | |
| ECHA InfoCard | 100.236.929 |
PubChem CID |
|
| UNII | |
CompTox Dashboard (EPA) |
|
| |
| |
| Properties | |
| C21H30O2 | |
| Molar mass | 314.469 g·mol−1 |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
| |
Biosynthesis
Within the Cannabis plant, CBC occurs mainly as cannabichromenic acid (CBCA, 2-COOH-CBC, CBC-COOH). Geranyl pyrophosphate and olivetolic acid combine to produce cannabigerolic 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 is decarboxylated, producing CBC. See also the biosynthetic scheme image below.[citation needed]
CBC biosynthetic scheme
Pharmacology
Cannabichromene has been hypothesized to affect THC psychoactivity, though in vivo effects have not been demonstrated.[4] CBC acts on the TRPV1 and TRPA1 receptors, interfering with their ability to break down endocannabinoids (chemicals such as anandamide and 2-AG that the body creates naturally).[5][unreliable source?] CBC has shown antitumor effects in breast cancer xenoplants in mice.[6] It also has anticonvulsant activity in a mouse model.[7]
In vitro, CBC binds weakly to CB1 and CB2 with binding affinities of 713 nM and 256 nM, respectively, which are significantly lower than that for THC with 35 nM at CB1.[8][9] acting as an agonist for cAMP stimulation and an antagonist at beta-arrestin.[8] Additionally, CBC is an agonist of TRPA1, and less potently TRPV3 and TRPV4.[2] CBC has two stereoisomers.