Cannabichromene

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Cannabichromene
(RS)-Cannabichromene.svg
Names
IUPAC name
2-Methyl-2-(4-methylpent-3-enyl)-7-pentyl-5-chromenol
Identifiers
  • 20675-51-8 ☑Y
3D model (JSmol)
  • Interactive image
ChEMBL
  • ChEMBL422704 ☒N
ChemSpider
  • 28064 ☒N
ECHA InfoCard 100.236.929
PubChem CID
  • 30219
Properties
C21H30O2
Molar mass 314.47 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 ☑Y☒N ?)
Infobox references

Cannabichromene (CBC) is one of the 113 cannabinoids found in the Cannabis plant and therefore can be also described as a phytocannabinoid – from ancient Greek phyton = "plant". It bears structural similarity to the other natural cannabinoids, including tetrahydrocannabinol, tetrahydrocannabivarin, cannabidiol, and cannabinol, among others.[1] Evidence has suggested that it may play a role in the anti-inflammatory[2] and anti-viral effects of cannabis, and it may have also antifungal properties.[3] Cannabichromene 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.[4] Another study showed that CBC helps promote neurogenesis.[5]

CBC is known to interact with many receptors in the brain. It is widely known 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 may result in some of its medicinal properties.[6] Also, in mice, its antiinflammatory activity appears to be modulated by the administration of THC and is independent of the CB2 receptor. This suggests an interplay of the two molecules.[7]

CBC has two stereoisomers. It is not scheduled by the Convention on Psychotropic Substances. CBC is non-psychotropic.[8]

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 (a key intermediate for multiple cannabinoids), which is cyclized by the enzyme CBCA synthase to give CBCA. Over time, or when heated, CBCA is decarboxylated, producing CBC. See biosynthetic scheme below the chemical data table.[citation needed]

CBC biosynthetic scheme

Animal research

The anti-inflammatory properties of CBC were studied in 1980 using the rat paw edema test and the erythrocyte membrane stabilization assay. CBC was found to be as effective as phenylbutazone (PBZ) at equivalent doses, but since CBC is less toxic than PBZ, it was concluded that larger doses of CBC may be employed to produce a greater therapeutic effect.[9]

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.[8] 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.[5]

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.[10]

In a 2015 study, CBC, together with other common phytocannabinoids, appeared to be promising in skin inflammatory conditions. Specifically CBC, cannabidivarin and tetrahydrocannabivarin showed promise to become highly efficient, novel anti-acne agents.[11]

References

  1. ^ Aizpurua-Olaizola O, Soydaner U, Öztürk E, Schibano D, Simsir Y, Navarro P, Etxebarria N, Usobiaga A (February 2016). "Evolution of the Cannabinoid and Terpene Content during the Growth of Cannabis sativa Plants from Different Chemotypes". Journal of Natural Products. 79 (2): 324–31. doi:10.1021/acs.jnatprod.5b00949. PMID 26836472. 
  2. ^ Romano B, Borrelli F, Fasolino I, Capasso R, Piscitelli F, Cascio M, Pertwee R, Coppola D, Vassallo L, Orlando P, Di Marzo V, Izzo A (May 2013). "The cannabinoid TRPA1 agonist cannabichromene inhibits nitric oxide production in macrophages and ameliorates murine colitis". British Journal of Pharmacology. 169 (1): 213–29. doi:10.1111/bph.12120. PMC 3632250Freely accessible. PMID 23373571. 
  3. ^ Turner CE, Elsohly MA (1981). "Biological activity of cannabichromene, its homologs and isomers". Journal of Clinical Pharmacology. 21 (8–9 Suppl): 283S–291S. doi:10.1002/j.1552-4604.1981.tb02606.x. PMID 7298870. 
  4. ^ El-Alfy AT, Ivey K, Robinson K, Ahmed S, Radwan M, Slade D, Khan I, ElSohly M, Ross S (June 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 2866040Freely accessible. PMID 20332000. 
  5. ^ a b Shinjyo N, Di Marzo V (November 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. 
  6. ^ Morales P, Hurst DP, Reggio PH (2017). "Molecular Targets of the Phytocannabinoids: A Complex Picture". Phytocannabinoids. Progress in the Chemistry of Organic Natural Products. 103. pp. 103–131. doi:10.1007/978-3-319-45541-9_4. ISBN 978-3-319-45539-6. PMC 5345356Freely accessible. PMID 28120232. 
  7. ^ DeLong GT, Wolf CE, Poklis A, Lichtman AH (November 2010). "Pharmacological evaluation of the natural constituent of Cannabis sativa, cannabichromene and its modulation by Δ(9)-tetrahydrocannabinol". Drug and Alcohol Dependence. 112 (1–2): 126–33. doi:10.1016/j.drugalcdep.2010.05.019. PMC 2967639Freely accessible. PMID 20619971. 
  8. ^ a b Maione S, Piscitelli F, Gatta L, Vita D, De Petrocellis L, Palazzo E, de Novellis V, Di Marzo V (February 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. PMC 3041249Freely accessible. PMID 20942863. 
  9. ^ Wirth PW, Watson ES, ElSohly M, Turner CE, Murphy JC (June 1980). "Anti-inflammatory properties of cannabichromene". Life Sciences. 26 (23): 1991–5. doi:10.1016/0024-3205(80)90631-1. PMID 7401911. 
  10. ^ Izzo AA, Capasso R, Aviello G, Borrelli F, Romano B, Piscitelli F, Gallo L, Capasso F, Orlando P, Di Marzo V (June 2012). "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 3417459Freely accessible. PMID 22300105. 
  11. ^ Oláh A, Markovics A, Szabó-Papp J, Szabó PT, Stott C, Zouboulis CC, Bíró T (September 2016). "Differential effectiveness of selected non-psychotropic phytocannabinoids on human sebocyte functions implicates their introduction in dry/seborrhoeic skin and acne treatment". Experimental Dermatology. 25 (9): 701–7. doi:10.1111/exd.13042. hdl:2437/243742. PMID 27094344. 
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