Cannabichromene

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Cannabichromene
Cannabichromene-skeletal.svg
Names
IUPAC name
2-Methyl-2-(4-methylpent-3-enyl)-7-pentyl-5-chromenol
Identifiers
20675-51-8 YesY
ChEMBL ChEMBL422704 N
ChemSpider 28064 N
Jmol-3D images Image
PubChem 30219
Properties
C21H30O2
Molar mass 314.46 g/mol
Except where noted otherwise, data is given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
 N verify (what isYesY/N?)
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. However, more research into the compound may be needed before any definite medical effects can be verified.[1]

CBC has two stereoisomers. It is not scheduled by the Convention on Psychotropic Substances. CBC is non-psychotropic.[2] Its boiling point is 220 degrees Celsius, 428 degrees Fahrenheit.[3]

Medical uses[edit]

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.[2] 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.[4]

In a 2012 animal study, CBC was shown to normalize gastrointestinal hypermotility (diarrhea) without reducing the transit time. The study notes that this of potential clinical interest, as the only drugs available for intestinal dysmotility are often associated with constipation. [5]

References[edit]

  1. ^ Gaoni, Y.; Mechoulam, R. (1966). "Cannabichromene, a new active principle in hashish". Chemical Communications 1: 20–1. doi:10.1039/C19660000020. 
  2. ^ a b 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. 
  3. ^ Skunk Pharma Search, Cannabinoid and Terpene info
  4. ^ 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. 
  5. ^ 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. Retrieved April 2015.