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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ChEMBL |
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ChemSpider |
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ECHA InfoCard | 100.236.929 |
PubChem CID |
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InChI
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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). N verify (what is YN ?) Infobox references |
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.[citation needed]
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][unreliable source?] 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.[9] Additionally, CBC is an agonist of TRPA1, and less potently TRPV3 and TRPV4.[3] CBC has two stereoisomers.
References
- ^ "Cannabichromene". PubChem. National Center for Biotechnology Information. 16 February 2019. Retrieved 12 February 2019.
- ^ Morales P, Hurst DP, Reggio PH (2017). "Molecular Targets of the Phytocannabinoids: A Complex Picture". Progress in the Chemistry of Organic Natural Products. 103: 103–31. doi:10.1007/978-3-319-45541-9_4. ISBN 978-3-319-45539-6. PMC 5345356. PMID 28120232.
- ^ a b c d 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. Vol. 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.
- ^ 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. doi:10.1021/acschemneuro.0c00677 PMID 33395525
- ^ a b 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. 10 (1): 20405. doi:10.1038/s41598-020-77175-y. ISSN 2045-2322. PMC 7684313. PMID 33230154.
- ^ 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. 46: 49–56. doi:10.1016/j.ntt.2014.09.003. PMID 25311884.
- v
- t
- e
(comparison)
Cannabibutols |
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Cannabichromenes | |
Cannabicyclols |
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Cannabidiols | |
Cannabielsoins |
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Cannabigerols | |
Cannabiphorols |
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Cannabinols | |
Cannabitriols |
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Cannabivarins |
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Delta-8-tetrahydrocannabinols |
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Delta-9-tetrahydrocannabinols | |
Delta-10-Tetrahydrocannabinols | |
Miscellaneous cannabinoids |
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Active metabolites |
- Arachidonoyl ethanolamide (AEA; anandamide)
- 2-Arachidonoylglycerol (2-AG)
- 2-Arachidonyl glyceryl ether (2-AGE; noladin ether)
- 2-Oleoylglycerol (2-OG)
- N-Arachidonoyl dopamine (NADA)
- N-Arachidonylglycine (NAGly)
- 2-Arachidonoyl lysophosphatidylinositol (2-ALPI)
- N-Arachidonoyl serotonin (AA-5-HT)
- Docosatetraenoylethanolamide (DEA)
- Lysophosphatidylinositol (LPI)
- Oleamide
- Oleoylethanolamide (OEA)
- Palmitoylethanolamide (PEA)
- RVD-Hpα
- Stearoylethanolamide (SEA)
- O-Arachidonoyl ethanolamine (O-AEA; virodhamine)
cannabinoid
receptor
agonists /
neocannabinoids
Classical cannabinoids (dibenzopyrans) |
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Non-classical cannabinoids |
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Adamantoylindoles |
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Benzimidazoles | |
Benzoylindoles |
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Cyclohexylphenols | |
Eicosanoids |
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Hydrocarbons | |
Indazole carboxamides | |
Indazole-3- carboxamides |
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Indole-3-carboxamides |
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Indole-3-carboxylates | |
Naphthoylindazoles | |
Naphthoylindoles |
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Naphthoylpyrroles | |
Naphthylmethylindenes | |
Naphthylmethylindoles | |
Phenylacetylindoles | |
Pyrazolecarboxamides |
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Pyrrolobenzoxazines | |
Quinolinyl esters | |
Tetramethylcyclo- propanoylindazoles | |
Tetramethylcyclo- propanoylindoles | |
Tetramethylcyclo- propylindoles | |
Others |
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enhancers
(inactivation inhibitors)
- 4-Nonylphenylboronic acid
- AM-404
- Arachidonoyl serotonin
- Arvanil
- BIA 10-2474
- Biochanin A
- CAY-10401
- CAY-10429
- Genistein
- Guineesine
- IDFP
- JNJ 1661010
- JNJ-42165279
- JZL184
- JZL195
- Kaempferol
- LY-2183240
- MK-4409
- O-1624
- O-2093
- Oleoylethanolamide (OEA)
- Olvanil
- Palmitoylethanolamide (PEA)
- PF-04457845
- PF-622
- PF-750
- PF-3845
- PHOP
- URB-447
- URB-597
- URB-602
- URB-754
- VDM-11
(antagonists/inverse
agonists/antibodies)
- AM-251
- AM-281
- AM-630
- AM-1387
- AM-4113
- AM-6527
- AM-6545
- BML-190
- Brizantin (Бризантин)
- CAY-10508
- CB-25
- CB-52
- CB-86
- Dietressa (Диетресса)
- Drinabant (AVE1625)
- Hemopressin
- Ibipinabant (SLV319)
- JTE-907
- LH-21
- LY-320,135
- MDA-77
- MJ-15
- MK-9470
- NESS-0327
- NIDA-41020
- O-606
- O-1184
- O-1248
- O-1918
- O-2050
- O-2654
- Otenabant (CP-945,598)
- PF-514273
- PipISB
- PSB-SB-487
- Rimonabant (SR141716)
- Rosonabant (E-6776)
- SR-144,528
- Surinabant (SR147778)
- Taranabant (MK-0364)
- TM-38837
- VCHSR
- See also: Cannabinoid receptor modulators (cannabinoids by pharmacology)
- List of: AM cannabinoids
- JWH cannabinoids
- Designer drugs § Synthetic cannabimimetics