Cannabichromene

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Cannabichromene
(RS)-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
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).
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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]

It, and its deriatives, are as abundant as cannabinols in cannabis.[2]

It is not active at CB1 or CB2 receptors but is an agonist of TRPA1 and less potently, an agonist of TRPV3 and TRPV4.[2]

CBC has two stereoisomers. 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 (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

Research[edit]

As of 2017, CBC is under laboratory research to identify its possible pharmacological properties.[2][3]

References[edit]

  1. ^ Aizpurua-Olaizola, Oier; Soydaner, Umut; Öztürk, Ekin; Schibano, Daniele; Simsir, Yilmaz; Navarro, Patricia; Etxebarria, Nestor; Usobiaga, Aresatz (2016). "Evolution of the Cannabinoid and Terpene Content during the Growth of Cannabis sativa Plants from Different Chemotypes". Journal of Natural Products. 79 (2): 324–331. doi:10.1021/acs.jnatprod.5b00949. PMID 26836472.
  2. ^ a b c Turner, Sarah E.; Williams, Claire M.; Iversen, Leslie; Whalley, Benjamin J. (2017). "Molecular Pharmacology of Phytocannabinoids". In Kinghorn, A. Douglas; Falk, Heinz; Gibbons, Simon; Kobayashi, Jun'ichi. Phytocannabinoids: Unraveling the Complex Chemistry and Pharmacology of Cannabis sativa. Progress in the Chemistry of Organic Natural Products. 103. Springer International Publishing. pp. 61–101. doi:10.1007/978-3-319-45541-9_3. ISBN 978-3-319-45539-6. PMID 28120231.
  3. ^ Morales, Paula; Hurst, Dow P.; Reggio, Patricia H. (2017). "Molecular Targets of the Phytocannabinoids: A Complex Picture". In Kinghorn, A. Douglas; Falk, Heinz; Gibbons, Simon; Kobayashi, Jun'ichi. Phytocannabinoids: Unraveling the Complex Chemistry and Pharmacology of Cannabis sativa. Progress in the Chemistry of Organic Natural Products. 103. Springer International Publishing. pp. 103–131. doi:10.1007/978-3-319-45541-9_4. ISBN 978-3-319-45539-6. PMC 5345356. PMID 28120232.