Cannabigerol Explained

Cannabigerol (CBG) is a non-psychoactive cannabinoid and minor constituent of cannabis.[1] [2] [3] It is one of more than 120identified cannabinoids found in the plant genus Cannabis.[4] [5] The compound is the decarboxylated form of cannabigerolic acid (CBGA), the parent molecule from which other cannabinoids are biosynthesized.[6] [7]

During plant growth, most of the CBG is converted into other cannabinoids, primarily tetrahydrocannabinol (THC) or cannabidiol (CBD), leaving about 1% CBG in the plant.[8] Some strains, however, produce larger amounts of CBG and CBGA, while having low quantities of other cannabinoids, like THC and CBD.[9] CBG is present not only in Cannabis sativa but also in Helichrysum umbraculigerum. The latter is considered to be the most abundant natural source of CBG.

The pharmacodynamics of CBG are complex. It is a relatively weak ligand of the cannabinoid receptors, where it acts as a weak partial agonist. Conversely, it is a much more potent agonist of the α2-adrenergic receptor, antagonist of the serotonin 5-HT1A receptor, and antagonist of the transient receptor potential channel TRPM8. CBG also has a variety of other actions that may additionally contribute to its effects.

Although CBG is sold as a dietary supplement, its effects and safety for human consumption are unknown. Safety concerns have been raised due to the potent activation of α2-adrenergic receptors by CBG, which may produce sedation and potentially undesirable cardiovascular effects like decreased heart rate and blood pressure.

Pharmacology

Pharmacodynamics

CBG lacks psychoactive, cannabimimetic, or psychotropic effects. It has been reported to reduce the psychotropic effects of tetrahydrocannabinol (THC). The compound has analgesic effects.[10] Preclinical research has also found that CBG reduces intraocular pressure, has antioxidant, anti-inflammatory, anti-tumoral, antibacterial, and antifungal activities, and has antidepressant-like, anxiolytic, neuromodulatory, neuroprotective, dermatological, pro-nausea, and appetite-stimulating effects, among others.[11] [12]

CBG has many identified pharmacodynamic actions and its mechanism of action appears to be from interactions with multiple targets.

CBG is a weak ligand of the cannabinoid CB1 and CB2 receptors with affinities (Ki) of 380–2,600nM and 153–3,460nM, respectively.[13] [14] It is a weak partial agonist or antagonist of both of these receptors. There is no information on the binding or activity of CBG at the GPR55 (the potential non-homologous CB3 receptor). CBG has relatively low affinity for the cannabinoid receptors, with approximately 5-fold lower affinity for the CB1 receptor and 27-fold lower affinity for the CB2 receptor than THC. The low affinity of CBG for the CB1 receptor may in part be involved in its lack of psychoactivity.

CBG is a highly potent agonist of the α2-adrenergic receptor (= 0.2–72.8nM) and a moderately potent antagonist of the serotonin 5-HT1A receptor (KB = 51.9nM).[15] Activation of the α2-adrenergic receptor by CBG might produce effects including sedation, dry mouth, and decreased heart rate and blood pressure. This has raised safety concerns about CBG. The actions of CBG at the α2-adrenergic receptor and 5-HT1A receptor are of far greater potency than its interactions with the cannabinoid receptors and are more likely to be involved in its pharmacodynamic effects. These activities may specifically contribute to the analgesic and pro-nausea effects of CBG.

The compound is a weak agonist of the transient receptor potential channels TRPA1 (= 700nM), TRPV1 (= 1,300nM), TRPV2 (= 1,720nM), TRPV3 (= 1,000nM), and TRPV4 (= 5,100nM) (efficacy 18–100% at these targets) and a more potent antagonist of the transient receptor potential channel TRPM8 (= 160nM). It is also a weak agonist of the peroxisome proliferator-activated receptor PPAR-γ (= 1,270–15,700nM).

CBG is a voltage-gated sodium channel (VGSC) blocker (Nav1.1, Nav1.2, Nav1.5, and Nav1.7) and voltage-dependent calcium channel (VDCC) blocker.[16] Inhibition of VGSCs may be involved in the analgesic effects of CBG.

It shows no inhibition of several endocannabinoid-metabolizing enzymes including fatty acid amide hydrolase (FAAH), diacylglycerol lipase (DGL), and N-acylethanolamine acid amide hydrolase (NAAA). However, other research has found that CBG does inhibit FAAH and DGL, as well as monoacylglycerol lipase (MAGL), although it is less potent as an inhibitor of FAAH than cannabidiol (CBD). Aside from endocannabinoid-metabolizing enzymes, CBG is a weak inhibitor of the cyclooxygenase COX-1 and COX-2 enzymes (30% inhibition of each at 25,000nM). In addition, it has been found to inhibit both the metabolism and reuptake of anandamide.

Pharmacokinetics

The pharmacokinetics of CBG have been studied in animals and to a lesser extent in humans. CBG is metabolized in the liver by CYP2J2, similarly to other cannabinoids as well as endocannabinoids.

Chemistry

CBG is a highly lipophilic and hydrophobic compound. Its predicted log P ranges from 7.0 to 7.5.[17] [18]

Synthetic derivatives of CBG have been synthesized and studied.

History

CBG was isolated from cannabis in 1964.

Society and culture

Legal status

CBG is not scheduled by the United Nations Convention on Psychotropic Substances. In the United States, CBG derived from marijuana is illegal under the Controlled Substances Act, while CBG derived from hemp is legal, as long as the hemp THC content is less than 0.3% of dry weight.[19] [20]

In Switzerland, it is legal to produce hemp rich in CBG as a tobacco substitute, as long as its THC content remains below 1.0%.[21]

Regulation

As of 2022, the US Food and Drug Administration has issued numerous warning letters to American companies for illegally marketing cannabis supplement products, including one selling CBG products with unproven illegal claims of efficacy against the COVID-19 virus and inflammation.[22]

Biosynthesis

The biosynthesis of CBG begins by loading hexanoyl-CoA onto a polyketide synthase assembly protein and subsequent condensation with three molecules of malonyl-CoA.[23] This polyketide is cyclized to olivetolic acid via olivetolic acid cyclase, and then prenylated with a ten carbon isoprenoid precursor, geranyl pyrophosphate, using an aromatic prenyltransferase enzyme, geranyl-pyrophosphate—olivetolic acid geranyltransferase, to biosynthesize cannabigerolic acid, which can then be decarboxylated to yield CBG.

Research

, no clinical research has been conducted to test the specific effects of CBG in humans. CBG is under laboratory research to determine its pharmacological properties and potential effects in disease conditions, with no conclusions about therapeutic effects or safety, as of 2021.[24] [25] A clinical trial published in July 2024, one of the first in humans, assessed the effects of CBG on anxiety, stress, and mood.[26] [27]

Notes and References

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  2. Ghovanloo MR, Dib-Hajj SD, Goodchild SJ, Ruben PC, Waxman SG . Non-psychotropic phytocannabinoid interactions with voltage-gated sodium channels: An update on cannabidiol and cannabigerol . Front Physiol . 13 . 1066455 . 2022 . 36439273 . 9691960 . 10.3389/fphys.2022.1066455 . free .
  3. Morales P, Reggio PH, Jagerovic N . An Overview on Medicinal Chemistry of Synthetic and Natural Derivatives of Cannabidiol . Frontiers in Pharmacology . 8 . 422 . 2017 . 28701957 . 5487438 . 10.3389/fphar.2017.00422 . free .
  4. Book: ElSohly MA, Radwan MM, Gul W, Chandra S, Galal A . Phytochemistry of Cannabis sativa L. . Phytochemistry of Cannabis sativa L . 103 . 1–36 . 2017 . 28120229 . 10.1007/978-3-319-45541-9_1 . 978-3-319-45539-6 . Progress in the Chemistry of Organic Natural Products .
  5. Book: Turner SE, Williams CM, Iversen L, Whalley BJ . Molecular Pharmacology of Phytocannabinoids . Progress in the Chemistry of Organic Natural Products . Phytocannabinoids . 103 . 61–101 . 2017 . 28120231 . 10.1007/978-3-319-45541-9_3 . 978-3-319-45539-6 .
  6. Nachnani R, Raup-Konsavage WM, Vrana KE . The pharmacological case for cannabigerol . The Journal of Pharmacology and Experimental Therapeutics. 376 . 2 . 2021 . 0022-3565 . 33168643 . 10.1124/jpet.120.000340 . 204–212. 226296897 . free .
  7. Web site: Cannabigerol; ID 5315659 . PubChem, National Library of Medicine, US National Institutes of Health . 2 July 2022 . 7 July 2022.
  8. Aizpurua-Olaizola O, Soydaner U, Öztürk E, Schibano D, Simsir Y, Navarro P, Etxebarria N, Usobiaga A . 6 . 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 . February 2016 . 26836472 . 10.1021/acs.jnatprod.5b00949 .
  9. Zagožen M, Čerenak A, Kreft S . 2021-09-01 . Cannabigerol and cannabichromene in Cannabis sativa L. . Acta Pharmaceutica . en . 71 . 3 . 355–364 . 10.2478/acph-2021-0021. 36654096 . 231543630 .
  10. Evans FJ . Cannabinoids: the separation of central from peripheral effects on a structural basis . Planta Med . 57 . 7 Suppl . S60–S67 . October 1991 . 17226225 . 10.1055/s-2006-960231 .
  11. Jastrząb A, Jarocka-Karpowicz I, Skrzydlewska E . The Origin and Biomedical Relevance of Cannabigerol . Int J Mol Sci . 23 . 14 . July 2022 . 7929 . 35887277 . 9322760 . 10.3390/ijms23147929 . free .
  12. Zagožen M, Čerenak A, Kreft S . Cannabigerol and cannabichromene in Cannabis sativa L . Acta Pharm . 71 . 3 . 355–364 . September 2021 . 36654096 . 10.2478/acph-2021-0021 .
  13. Sampson PB . Phytocannabinoid Pharmacology: Medicinal Properties of Cannabis sativa Constituents Aside from the "Big Two" . J Nat Prod . 84 . 1 . 142–160 . January 2021 . 33356248 . 10.1021/acs.jnatprod.0c00965 .
  14. Web site: Liu . Tiqing . BindingDB BDBM50318487 CHEMBL497318::Cannabigerol . BindingDB . 14 August 2024.
  15. Cascio MG, Gauson LA, Stevenson LA, Ross RA, Pertwee RG . Evidence that the plant cannabinoid cannabigerol is a highly potent alpha2-adrenoceptor agonist and moderately potent 5HT1A receptor antagonist . Br J Pharmacol . 159 . 1 . 129–141 . January 2010 . 20002104 . 2823359 . 10.1111/j.1476-5381.2009.00515.x .
  16. Ghovanloo MR, Estacion M, Higerd-Rusli GP, Zhao P, Dib-Hajj S, Waxman SG . Inhibition of sodium conductance by cannabigerol contributes to a reduction of dorsal root ganglion neuron excitability . Br J Pharmacol . 179 . 15 . 4010–4030 . August 2022 . 35297036 . 10.1111/bph.15833 .
  17. Web site: Cannabigerol: Uses, Interactions, Mechanism of Action . DrugBank Online . 1 February 2019 . 14 August 2024.
  18. Web site: Cannabigerol . ChemSpider . 14 August 2024 . 14 August 2024.
  19. Web site: FDA Regulation of Cannabis and Cannabis-Derived Products, Including Cannabidiol (CBD) . US Food and Drug Administration . 7 July 2022 . 21 January 2021.
  20. Web site: USC > Title 21 > Chapter 13 > Subchapter I > Part A > § 802. Definitions: (16). 2016. Government Publishing Office - US Code.
  21. Web site: BAG . Bundesamt für Gesundheit . Häufig gestellte Fragen (FAQ) zu Tabakersatzprodukten mit THC-armem Hanf mit CBD . 2022-07-06 . www.bag.admin.ch . de.
  22. Web site: Ashley D . 28 March 2022 . Warning Letter to Greenway Herbal Products LLC; Ref. 627042 . 7 July 2022 . Office of Compliance, Center for Drug Evaluation and Research, Food and Drug Administration.
  23. Gagne SJ, Stout JM, Liu E, Boubakir Z, Clark SM, Page JE . Identification of olivetolic acid cyclase from Cannabis sativa reveals a unique catalytic route to plant polyketides . Proceedings of the National Academy of Sciences of the United States of America . 109 . 31 . 12811–12816 . July 2012 . 22802619 . 3411943 . 10.1073/pnas.1200330109 . free . 2012PNAS..10912811G .
  24. Book: Phytocannabinoids . Morales P, Hurst DP, Reggio PH . 2017 . 978-3-319-45539-6 . Progress in the Chemistry of Organic Natural Products . 103 . 103–131 . Molecular Targets of the Phytocannabinoids: A Complex Picture . 10.1007/978-3-319-45541-9_4 . 5345356 . 28120232.
  25. Couch DG, Maudslay H, Doleman B, Lund JN, O'Sullivan SE . March 2018 . The Use of Cannabinoids in Colitis: A Systematic Review and Meta-Analysis . Inflammatory Bowel Diseases . 24 . 4 . 680–697 . 10.1093/ibd/izy014 . 29562280 . free.
  26. Cuttler C, Stueber A, Cooper ZD, Russo E . Acute effects of cannabigerol on anxiety, stress, and mood: a double-blind, placebo-controlled, crossover, field trial . Sci Rep . 14 . 1 . 16163 . July 2024 . 39003387 . 11246434 . 10.1038/s41598-024-66879-0 . 2024NatSR..1416163C .
  27. Web site: Cannabigerol (CBG) Reduces Anxiety and Improves Memory . Neuroscience News . 31 July 2024 . 14 August 2024.