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;
	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	314.47 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

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.

CBC biosynthetic scheme

Research

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

References

↑ 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.
1 2 3 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.
↑ 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.

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[pmid26836472-1] 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.

[Turner2017-2] 1 2 3 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.