Cannabichromene Explained

Cannabichromene (CBC), also called cannabichrome, cannanbichromene, pentylcannabichromene or cannabinochromene,[1] exhibits anti-inflammatory properties in vitro, which may, theoretically, contribute to cannabis analgesic effects.[2] It is a phytocannabinoid, one of the hundreds of cannabinoids found in the Cannabis plant.[3] It bears structural similarity to the other natural cannabinoids, including tetrahydrocannabinol (THC), tetrahydrocannabivarin (THCV), cannabidiol (CBD), and cannabinol (CBN), among others.[3] [4] CBC and cannabinols are present in cannabis.[3] 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 93 °C, CBCA is decarboxylated, producing CBC. See also the biosynthetic scheme image below.

Pharmacology

Cannabichromene has been hypothesized to affect THC psychoactivity, though in vivo effects have not been demonstrated.[5] 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).[6] CBC has shown antitumor effects in breast cancer xenoplants in mice.[7] It also has anticonvulsant activity in a mouse model.[8]

In vitro, CBC binds weakly to CB1 and CB2 with binding affinities of 713 nM and 256 nM, respectively, which are significantly lower than that for THC with 35 nM at CB1.[9] [10] acting as an agonist for cAMP stimulation and an antagonist at beta-arrestin. Additionally, CBC is an agonist of TRPA1, and less potently TRPV3 and TRPV4.[3] CBC has two stereoisomers.

Notes and References

  1. Web site: Cannabichromene. . 16 February 2019 . PubChem . National Center for Biotechnology Information . 12 February 2019.
  2. Morales P, Hurst DP, Reggio PH . Molecular Targets of the Phytocannabinoids: A Complex Picture . Progress in the Chemistry of Organic Natural Products . 103 . 103–31 . 2017 . 28120232 . 5345356 . 10.1007/978-3-319-45541-9_4 . 978-3-319-45539-6 .
  3. Book: 28120231. 2017. Turner. Sarah E.. Claire M.. Williams. Leslie. Iversen. Leslie Iversen. Benjamin J.. Whalley. Molecular Pharmacology of Phytocannabinoids. Phytocannabinoids: Unraveling the Complex Chemistry and Pharmacology of Cannabis sativa. A. Douglas. Kinghorn. Heinz. Falk. Heinz Falk. Simon. Gibbons. Simon Gibbons. Jun'ichi. Kobayashi. Springer International Publishing. Progress in the Chemistry of Organic Natural Products. 103. 61–101. 10.1007/978-3-319-45541-9_3. 978-3-319-45539-6.
  4. Oier . Aizpurua-Olaizola . Umut . Soydaner . Ekin . Öztürk . Daniele . Schibano . Yilmaz . Simsir . Patricia . Navarro . Nestor . Etxebarria . Aresatz . Usobiaga . Evolution of the Cannabinoid and Terpene Content during the Growth of Cannabis sativa Plants from Different Chemotypes . . 79 . 2 . 324–331 . 2016 . 26836472 . 10.1021/acs.jnatprod.5b00949 .
  5. Ilan AB, Gevins A, Coleman M, ElSohly MA, de Wit H . Neurophysiological and subjective profile of marijuana with varying concentrations of cannabinoids . Behavioural Pharmacology . 16 . 5–6 . 487–96 . September 2005 . 16148455 . 10.1097/00008877-200509000-00023 . 827221 .
  6. Web site: What Is CBC (Cannabichromene)?. CNBS. en-US. 2019-03-31.
  7. 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 . 2006-09-01 . 10.1124/jpet.106.105247 . 16728591 . Ligresti . A. . Moriello . A. S. . Starowicz . K. . Matias . I. . Pisanti . S. . De Petrocellis . L. . Laezza . C. . Portella . G. . Bifulco . M. . Di Marzo . V. . 1341744 .
  8. Anderson LL, Ametovski A, Lin Luo J, Everett-Morgan D, McGregor IS, Banister SD, Arnold JC. Cannabichromene, Related Phytocannabinoids, and 5-Fluoro-cannabichromene Have Anticonvulsant Properties in a Mouse Model of Dravet Syndrome. ACS Chem Neurosci. 2021 Jan 20;12(2):330-339.
  9. Zagzoog . Ayat . Mohamed . Kawthar A. . Kim . Hye Ji J. . Kim . Eunhyun D. . Frank . Connor S. . Black . Tallan . Jadhav . Pramodkumar D. . Holbrook . Larry A. . Laprairie . Robert B. . 2020-11-23 . In vitro and in vivo pharmacological activity of minor cannabinoids isolated from Cannabis sativa . Scientific Reports . en . 10 . 1 . 20405 . 10.1038/s41598-020-77175-y . 33230154 . 7684313 . 2045-2322.
  10. Rosenthaler . Sarah . Pöhn . Birgit . Kolmanz . Caroline . Nguyen Huu . Chi . Krewenka . Christopher . Huber . Alexandra . Kranner . Barbara . Rausch . Wolf-Dieter . Moldzio . Rudolf . November 2014 . Differences in receptor binding affinity of several phytocannabinoids do not explain their effects on neural cell cultures . Neurotoxicology and Teratology . en . 46 . 49–56 . 10.1016/j.ntt.2014.09.003. 25311884 .

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