Cannabichromene

Cannabichromene
Names
	IUPAC name 2-Methyl-2-(4-methylpent-3-enyl)-7-pentyl-5-chromenol
Identifiers
CAS Number	20675-51-8 ;
3D model (JSmol)	Interactive image;
ChEMBL	ChEMBL422704 ;
ChemSpider	28064 ;
ECHA InfoCard	100.236.929
PubChem CID	30219;
UNII	K4497H250W ;
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 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	314.469 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), also called cannabichrome, cannanbichromene, pentylcannabichromene or cannabinochromene,^[1] is one of the hundreds of cannabinoids found in the Cannabis plant,^[2] and is therefore a phytocannabinoid. It bears structural similarity to the other natural cannabinoids, including tetrahydrocannabinol (THC), tetrahydrocannabivarin (THCV), cannabidiol (CBD), and cannabinol (CBN), among others.^[2]^[3] CBC and its derivatives are as abundant as cannabinols in cannabis.^[2] It is not scheduled by the Convention on Psychotropic Substances.

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 (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 200° F, CBCA is decarboxylated, producing CBC. See also the biosynthetic scheme image below.^{[citation needed]}

CBC biosynthetic scheme

Pharmacology

As of 2017, CBC is under laboratory research to identify its possible pharmacological properties. No in vivo human studies exist as of 2019.^[1]^[2]^[4]^[5] In vitro, CBC 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.

References

^ ^a ^b "Cannabichromene". PubChem. National Center for Biotechnology Information. 16 February 2019. Retrieved 12 February 2019.
^ ^a ^b ^c ^d ^e 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 (eds.). 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.
^ 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.
^ 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 (eds.). 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.
^ Delong, G. T.; Wolf, C. E.; Poklis, A.; Lichtman, A. H. (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 2967639. PMID 20619971.

[pubchem-1] "Cannabichromene". PubChem. National Center for Biotechnology Information. 16 February 2019. Retrieved 12 February 2019.

[Turner2017-2] 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 (eds.). 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.

[pmid26836472-3] 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.

[4] 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 (eds.). 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.

[5] Delong, G. T.; Wolf, C. E.; Poklis, A.; Lichtman, A. H. (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 2967639. PMID 20619971.

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