Cannabichromene

Last updated
Cannabichromene
(RS)-Cannabichromene.svg
CBC 3D BS.png
Names
IUPAC name
2-Methyl-2-(4-methylpent-3-enyl)-7-pentyl-5-chromenol
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.236.929 OOjs UI icon edit-ltr-progressive.svg
PubChem CID
UNII
  • 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 X mark.svgN
    Key: UVOLYTDXHDXWJU-UHFFFAOYSA-N X mark.svgN
  • 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
  • CCCCCC1=CC2=C(C=CC(O2)(C)CCC=C(C)C)C(=C1)O
Properties
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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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.

Contents

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 ]

CBC biosynthetic scheme Biosynthesis of CBC.png
CBC biosynthetic scheme

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.

Related Research Articles

<span class="mw-page-title-main">Tetrahydrocannabinol</span> Psychoactive component of cannabis

Tetrahydrocannabinol (THC) is a cannabinoid found in cannabis. It is the principal psychoactive constituent of cannabis and one of at least 113 total cannabinoids identified on the plant. Although the chemical formula for THC (C21H30O2) describes multiple isomers, the term THC usually refers to the delta-9-THC isomer with chemical name (−)-trans-Δ9-tetrahydrocannabinol. It is a colorless oil.

<span class="mw-page-title-main">Cannabinoid</span> Compounds found in cannabis

Cannabinoids are several structural classes of compounds found in the cannabis plant primarily and most animal organisms or as synthetic compounds. The most notable cannabinoid is the phytocannabinoid tetrahydrocannabinol (THC) (delta-9-THC), the primary psychoactive compound in cannabis. Cannabidiol (CBD) is also a major constituent of temperate cannabis plants and a minor constituent in tropical varieties. At least 100 distinct phytocannabinoids have been isolated from cannabis, although only four have been demonstrated to have a biogenetic origin. It was reported in 2020 that phytocannabinoids can be found in other plants such as rhododendron, licorice and liverwort, and earlier in Echinacea.

<span class="mw-page-title-main">Cannabinoid receptor</span> Group of receptors to cannabinoid compounds

Cannabinoid receptors, located throughout the body, are part of the endocannabinoid system of vertebrates– a class of cell membrane receptors in the G protein-coupled receptor superfamily. As is typical of G protein-coupled receptors, the cannabinoid receptors contain seven transmembrane spanning domains. Cannabinoid receptors are activated by three major groups of ligands:

<i>Cannabis sativa</i> Plant species

Cannabis sativa is an annual herbaceous flowering plant. The species was first classified by Carl Linnaeus in 1753. The specific epithet sativa means 'cultivated'. Indigenous to Eastern Asia, the plant is now of cosmopolitan distribution due to widespread cultivation. It has been cultivated throughout recorded history and used as a source of industrial fiber, seed oil, food, and medicine. It is also used as a recreational drug and for religious and spiritual purposes.

<span class="mw-page-title-main">Cannabinol</span> Naturally-occurring cannabinoid

Cannabinol (CBN) is a mildly psychoactive phytocannabinoid that acts as a low affinity partial agonist at both CB1 and CB2 receptors. This activity at CB1 and CB2 receptors constitutes interaction of CBN with the endocannabinoid system (ECS).

<span class="mw-page-title-main">Cannabidiol</span> Phytocannabinoid discovered in 1940

Cannabidiol (CBD) is a phytocannabinoid, one of 113 identified cannabinoids in cannabis plants, along with tetrahydrocannabinol (THC), and accounts for up to 40% of the plant's extract. Medically, it is an anticonvulsant used to treat multiple forms of epilepsy. It was discovered in 1940 and, as of 2024 clinical research on CBD included studies related to the treatment of anxiety, addiction, psychosis, movement disorders, and pain, but there is insufficient high-quality evidence that CBD is effective for these conditions. CBD is sold as an herbal dietary supplement and promoted with yet unproven claims of particular therapeutic effects.

<span class="mw-page-title-main">Tetrahydrocannabivarin</span> Homologue of tetrahydrocannabinol

Tetrahydrocannabivarin is a homologue of tetrahydrocannabinol (THC) having a propyl (3-carbon) side chain instead of pentyl (5-carbon), making it non-psychoactive in lower doses. It has been shown to exhibit neuroprotective activity, appetite suppression, glycemic control and reduced side effects compared to THC, making it a potential treatment for management of obesity and diabetes. THCV was studied by Roger Adams as early as 1942.

<span class="mw-page-title-main">Cannabivarin</span> Chemical compound

Cannabivarin (CBV), also known as cannabivarol, is considered a non-psychoactive cannabinoid — it does not produce the euphoric side effects found in THC. Minor amounts of CBV are found in the hemp plant Cannabis sativa. It is an analog of cannabinol (CBN) with the side chain shortened by two methylene bridges (-CH2-). CBV is an oxidation product of tetrahydrocannabivarin (THCV, THV).

<span class="mw-page-title-main">11-Hydroxy-THC</span> Active metabolite of Δ9-THC

11-Hydroxy-Δ9-tetrahydrocannabinol, usually referred to as 11-hydroxy-THC is the main active metabolite of tetrahydrocannabinol (THC), which is formed in the body after Δ9-THC is consumed.

<span class="mw-page-title-main">Cannabigerol</span> Minor cannabinoid

Cannabigerol (CBG) is a non-psychoactive cannabinoid and minor constituent of cannabis. It is one of more than 120 identified cannabinoids found in the plant genus Cannabis. The compound is the decarboxylated form of cannabigerolic acid (CBGA), the parent molecule from which other cannabinoids are biosynthesized.

<span class="mw-page-title-main">Tetrahydrocannabutol</span> Chemical compound

Δ9-Tetrahydrocannabutol is a phytocannabinoid found in cannabis that is a homologue of tetrahydrocannabinol (THC), the main active component of Cannabis. Structurally, they are only different by the pentyl side chain being replaced by a butyl side chain. THCB was studied by Roger Adams as early as 1942

<span class="mw-page-title-main">Tetrahydrocannabinolic acid</span> THC precursor

Tetrahydrocannabinolic acid is a precursor of tetrahydrocannabinol (THC), an active component of cannabis.

The entourage effect is a hypothesis that cannabis compounds other than tetrahydrocannabinol (THC) act synergistically with it to modulate the overall psychoactive effects of the plant.

<span class="mw-page-title-main">Tetrahydrocannabiphorol</span> Cannabinoid agonist compound

Tetrahydrocannabiphorol (THCP) is a potent phytocannabinoid, a CB1 and CB2 receptor agonist which was known as a synthetic homologue of tetrahydrocannabinol (THC), but for the first time in 2019 was isolated as a natural product in trace amounts from Cannabis sativa.

<span class="mw-page-title-main">Δ-8-Tetrahydrocannabinol</span> Isomer of tetrahydrocannabinol

Δ-8-tetrahydrocannabinol is a psychoactive cannabinoid found in the cannabis plant. It is an isomer of delta-9-tetrahydrocannabinol, the compound commonly known as THC, with which it co-occurs in hemp; natural quantities of ∆8-THC found in hemp are low. Psychoactive effects are similar to that of Δ9-THC, with central effects occurring by binding to cannabinoid receptors found in various regions of the brain.

<span class="mw-page-title-main">Tetrahydrocannabiorcol</span> Chemical compound

Δ9-Tetrahydrocannabiorcol (Δ9-THCC, (C1)-Δ9-THC) is a phytocannabinoid found in Cannabis pollen. It is a homologue of THC and THCV with the alkyl side chain replaced by a smaller methyl group. Unlike THC and THCV, THCC has negligible affinity for the CB1 and CB2 cannabinoid receptors because of the smaller methyl group and does not have psychoactive effects as a result, but conversely it is significantly more potent than THC or THCV as an activator of the TRPA1 calcium channel which plays an important role in pain perception, and it has been shown to produce analgesic effects via activation of spinal TRPA1 channels. THCC was studied by Roger Adams as early as 1942.

<span class="mw-page-title-main">Δ-10-Tetrahydrocannabinol</span> Isomer of tetrahydrocannabinol

Δ-10-Tetrahydrocannabinol is a positional isomer of tetrahydrocannabinol, discovered in the 1980s. Two epimers have been reported in the literature, with the 9-methyl group in either the (R) or (S) conformation; of these, the (R) epimer appears to be the more active isomer as well as the double bond in the 10th position instead of the 9th maintaining about 30 to 40 percent the potency of delta-9-THC. Δ10-THC has rarely been reported as a trace component of natural cannabis, though it is thought to be a degradation product similar to cannabinol rather than being produced by the plant directly. However, it is found more commonly as an impurity in synthetic delta-8-THC produced from cannabidiol and can also be synthesized directly from delta-9-THC.

<span class="mw-page-title-main">Hexahydrocannabinol</span> Hydrogenated derivative of THC

Hexahydrocannabinol (HHC) is a hydrogenated derivative of tetrahydrocannabinol (THC). It is a naturally occurring phytocannabinoid that has rarely been identified as a trace component in Cannabis sativa, but can also be produced synthetically by firstly acid cyclization of cannabidiol and then hydrogenation of tetrahydrocannabinol. The synthesis and bioactivity of HHC was first reported in 1940 by Roger Adams.

<span class="mw-page-title-main">Cannabicitran</span> Chemical compound

Cannabicitran (CBTC) is a phytocannabinoid first isolated in 1974 as a trace component of Cannabis sativa. Structurally related compounds can be found in some other plants. It is not psychoactive, but was found to reduce intraocular pressure in tests on rabbits, which may reflect agonist activity at the NAGly receptor that is known to be a target of many structurally related cannabinoids.

Cannabinoids are compounds found in the cannabis plant or synthetic compounds that can interact with the endocannabinoid system. The most notable cannabinoid is the phytocannabinoid tetrahydrocannabinol (THC) (Delta-9-THC), the primary intoxicating compound in cannabis. Cannabidiol (CBD) is another major constituent of some cannabis plants. Conversion of CBD to THC can occur when CBD is heated to temperatures between 250–300 °C, potentially leading to its partial transformation into THC.

References

  1. ↑ "Cannabichromene". PubChem. National Center for Biotechnology Information. 16 February 2019. Retrieved 12 February 2019.
  2. ↑ Morales P, Hurst DP, Reggio PH (2017). "Molecular Targets of the Phytocannabinoids: A Complex Picture". Phytocannabinoids. Progress in the Chemistry of Organic Natural Products. Vol. 103. pp. 103–31. doi:10.1007/978-3-319-45541-9_4. ISBN   978-3-319-45539-6. PMC   5345356 . PMID   28120232.
  3. 1 2 3 4 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.
  4. ↑ 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.
  5. ↑ 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.
  6. ↑ "What Is CBC (Cannabichromene)?". CNBS. Retrieved 2019-03-31.
  7. ↑ 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.
  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. doi : 10.1021/acschemneuro.0c00677 PMID   33395525
  9. 1 2 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.
  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. 46: 49–56. Bibcode:2014NTxT...46...49R. doi:10.1016/j.ntt.2014.09.003. PMID   25311884.
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