Contents

Cannabichromene

Cannabichromene

Names
IUPAC name 2-Methyl-2-(4-methylpent-3-enyl)-7-pentyl-5-chromenol
Identifiers
CAS Number	20675-51-8 Y
3D model (JSmol)	Interactive image
ChEMBL	ChEMBL422704 N
ChemSpider	28064 N
ECHA InfoCard	100.236.929
PubChem CID	30219
UNII	K4497H250W Y
CompTox Dashboard (EPA)	DTXSID80942873
InChI InChI=1S/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 N Key: UVOLYTDXHDXWJU-UHFFFAOYSA-N N 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 Key: UVOLYTDXHDXWJU-UHFFFAOYAG
SMILES CCCCCC1=CC2=C(C=CC(O2)(C)CCC=C(C)C)C(=C1)O
Properties
Chemical formula	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). N verify (what is YN ?) Infobox references

Chemical compound

Cannabichromene (CBC), also called cannabichrome, cannanbichromene, pentylcannabichromene or cannabinochromene,^[1] exhibits anti-inflammatory properties in vitro, which may, theoretically, contribute to cannabis analgesic effects.^[2] It is a phytocannabinoid, one of the hundreds of cannabinoids found in the Cannabis plant.^[3] It bears structural similarity to the other natural cannabinoids, including tetrahydrocannabinol (THC), tetrahydrocannabivarin (THCV), cannabidiol (CBD), and cannabinol (CBN), among others.^[3][4] CBC and cannabinols are present in cannabis.^[3] It is not scheduled by the Convention on Psychotropic Substances.

Biosynthesis[edit]

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]}

Pharmacology[edit]

Cannabichromene has been hypothesized to affect THC psychoactivity, though in vivo effects have not been demonstrated.^[5] 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).^{[6][unreliable source?]} CBC has shown antitumor effects in breast cancer xenoplants in mice.^[7] It also has anticonvulsant activity in a mouse model.^[8]

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.^[9][10] acting as an agonist for cAMP stimulation and an antagonist at beta-arrestin.^[9] Additionally, CBC is an agonist of TRPA1, and less potently TRPV3 and TRPV4.^[3] CBC has two stereoisomers.

References[edit]