Cannabichromene
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IUPAC name
2-Methyl-2-(4-methylpent-3-enyl)-7-pentyl-5-chromenol
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3D model (JSmol)
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ECHA InfoCard | 100.236.929 |
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Properties | |
Chemical formula
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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). | |
what is ?) | (|
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. It is more common in tropical cannabis varieties.[citation needed]
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]
Pharmacology[]
CBC is non-psychoactive and does not affect the psychoactivity of THC.[4] CBC acts on the TRPV1 and TRPA1 receptors, interfering with their ability to break down endocannabinoids (chemicals such as anandamide and 2-AG that the body creates naturally).[5] CBC has shown antitumor effects in breast cancer xenoplants in mice.[6]
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][7][8] 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[]
- ^ Jump up to: a b "Cannabichromene". PubChem. National Center for Biotechnology Information. 16 February 2019. Retrieved 12 February 2019.
- ^ Jump up to: 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.
- ^ Ilan AB, Gevins A, Coleman M, ElSohly MA, de Wit H (September 2005). "Neurophysiological and subjective profile of marijuana with varying concentrations of cannabinoids". Behavioural Pharmacology. 16 (5–6): 487–96. doi:10.1097/00008877-200509000-00023. PMID 16148455. S2CID 827221.
- ^ "What Is CBC (Cannabichromene)?". CNBS. Retrieved 2019-03-31.
- ^ Ligresti, A.; Moriello, A. S.; Starowicz, K.; Matias, I.; Pisanti, S.; De Petrocellis, L.; Laezza, C.; Portella, G.; Bifulco, M.; Di Marzo, V. (2006-09-01). "Antitumor Activity of Plant Cannabinoids with Emphasis on the Effect of Cannabidiol on Human Breast Carcinoma | Journal of Pharmacology and Experimental Therapeutics". Journal of Pharmacology and Experimental Therapeutics. 318 (3): 1375–1387. doi:10.1124/jpet.106.105247. PMID 16728591. S2CID 1341744.
- ^ 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.
- Cannabinoids
- Chromenes
- Phenols