Cannabichromene

Cannabichromene

Names
IUPAC name 2-Methyl-2-(4-methylpent-3-enyl)-7-pentyl-5-chromenol
Identifiers
CAS Number	20675-51-8
3D model (Jmol)	Interactive image
ChEMBL	ChEMBL422704
ChemSpider	28064
ECHA InfoCard	100.236.929
PubChem	30219
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 Key: UVOLYTDXHDXWJU-UHFFFAOYSA-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	314.46 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Cannabichromene (CBC) is a cannabinoid found in the Cannabis plant. It bears structural similarity to the other natural cannabinoids, including tetrahydrocannabinol, tetrahydrocannabivarin, cannabidiol, and cannabinol, among others. Evidence has suggested that it may play a role in the anti-inflammatory and anti-viral effects of cannabis, and may contribute to the overall analgesic effects of medical cannabis. A study done in March 2010 showed that CBC along with cannabidiol and tetrahydrocannabinol have antidepressant effects.^[1] Another study showed that CBC helps promote neurogenesis.^[2]

CBC is known to interact with many receptors in the brain. Many people know that the cannabinoids interact with the CB1 and CB2 receptors, but they also interact with others. CBC in particular is known to interact with the TRPV1 and TRPA1 receptors as well, which results in some of its medicinal properties.^[3]

CBC has two stereoisomers. It is not scheduled by the Convention on Psychotropic Substances. CBC is non-psychotropic.^[4] Its boiling point is 220 degrees Celsius, 428 degrees Fahrenheit.^[5]

Research

A 2011 study in the British Journal of Pharmacology found that CBD and CBC stimulated descending pathways of antinociception and caused analgesia by interacting with several target proteins involved in nociceptive control.^[4] A study in Neurochemistry International suggested that cannabichromene might stimulate the growth of brain cells by stimulating adult neural stem progenitor cells (NSPCs). The study said "our results suggest that CBC raises the viability of NSPCs while inhibiting their differentiation into astroglia, possibly through up-regulation of ATP and adenosine signalling.^[6]

In a 2012 animal study, CBC was shown to normalize gastrointestinal hypermotility (diarrhea) without reducing the transit time. The study notes that this is of potential clinical interest, as the only drugs available for intestinal dysmotility are often associated with constipation.^[7]

References

1. El-Alfy, A. T.; Ivey, K; Robinson, K; Ahmed, S; Radwan, M; Slade, D; Khan, I; Elsohly, M; Ross, S (2010). "Antidepressant-like effect of delta9-tetrahydrocannabinol and other cannabinoids isolated from Cannabis sativa L". Pharmacology Biochemistry and Behavior. 95 (4): 434–42. doi:10.1016/j.pbb.2010.03.004. PMC 2866040. PMID 20332000.
2. Shinjyo, N.; Di Marzo, V. (2013). "The effect of cannabichromene on adult neural stem/progenitor cells". Neurochemistry International. 63 (5): 432–7. doi:10.1016/j.neuint.2013.08.002. PMID 23941747.
3. https://www.woahstork.com/blog/cbc/
4. Maione, Sabatino; Piscitelli, Fabiana; Gatta, Luisa; Vita, Daniela; De Petrocellis, Luciano; Palazzo, Enza; De Novellis, Vito; Di Marzo, Vincenzo (2011). "Non-psychoactive cannabinoids modulate the descending pathway of antinociception in anaesthetized rats through several mechanisms of action". British Journal of Pharmacology. 162 (3): 584–96. doi:10.1111/j.1476-5381.2010.01063.x. PMID 20942863.
5. Skunk Pharma Search, Cannabinoid and Terpene info
6. Shinjyo, Noriko; Di Marzo, Vincenzo (2013). "The effect of cannabichromene on adult neural stem/progenitor cells". Neurochemistry International. 63 (5): 432–7. doi:10.1016/j.neuint.2013.08.002. PMID 23941747.
7. Izzo A, Capasso R, Aviello G, Borrelli F, Romano B, Piscitelli F, Gallo L, Capasso F, Orlando P, Di Marzo V. (2012-05-17). "Inhibitory effect of cannabichromene, a major non-psychotropic cannabinoid extracted from Cannabis sativa, on inflammation-induced hypermotility in mice". British Journal of Pharmacology. 166 (4): 1444–60. doi:10.1111/j.1476-5381.2012.01879.x. PMC 3417459. PMID 22300105. Check date values in: |access-date= (help);