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Script assisted update of identifiers for the Chem/Drugbox validation project (updated: 'CAS_number').
CBG isn't found in Helichrysum, if we look at the citation used in the study that was cited for the claim we will see it contains analogs of CBG dubbed "Heli-CBG" (which is like a benzyl tailchain analog like what Perrottetinene is to THC) and 3-Hydroxy-CBG but not CBG itself
 
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{{Short description|Minor cannabinoid}}
{{Drugbox
{{Drugbox
| Verifiedfields = changed
| Verifiedfields = verified
| Watchedfields = verified
| verifiedrevid = 399704244
| verifiedrevid = 460016346
| IUPAC_name = 2-[(2E)-3,7-dimethylocta-2,6-dienyl]-5-pentyl-benzene-1,3-diol
| IUPAC_name = 2-[(2''E'')-3,7-Dimethylocta-2,6-dienyl]-5-pentyl-benzene-1,3-diol
| image = CBG.png
| image = Cannabigerol-skeletal.svg
| width = 225px
| image2 = Cannabigerol molecule ball.png
| width2 = 225px


<!--Clinical data-->
<!-- Clinical data -->
| tradename =
| tradename =
| pregnancy_category =
| pregnancy_category =
| legal_US = Unscheduled
| legal_status =
| legal_status =
| routes_of_administration =
| routes_of_administration =


<!--Pharmacokinetic data-->
<!-- Pharmacokinetic data -->
| bioavailability =
| bioavailability =
| protein_bound =
| protein_bound =
| metabolism =
| metabolism =
| metabolites =
| elimination_half-life =
| elimination_half-life =
| excretion =
| excretion =


<!--Identifiers-->
<!-- Identifiers -->
| CAS_number_Ref = {{cascite|correct|??}}
| CAS_number_Ref = {{cascite|correct|CAS}}
| CAS_number = <!-- blanked - oldvalue: 25654-31-3 -->
| CAS_number = 25654-31-3
| ATC_prefix =
| ATC_prefix = None
| ATC_suffix =
| ATC_suffix =
| PubChem = 5315659
| PubChem = 5315659
| IUPHAR_ligand = 11094
| DrugBank = DB14734
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 4474921
| ChemSpiderID = 4474921
| ChEMBL_Ref = {{ebicite|changed|EBI}}
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = J1K406072N
| KEGG = C20219
| ChEBI = 69477
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 497318
| ChEMBL = 497318
| NIAID_ChemDB =
| PDB_ligand =
| synonyms = CBG


<!--Chemical data-->
<!-- Chemical data -->
| C=21 | H=32 | O=2
| chemical_formula = C<sub>21</sub>H<sub>32</sub>O<sub>2</sub>
| SMILES = Oc1cc(cc(O)c1C/C=C(\C)CC\C=C(/C)C)CCCCC

| molecular_weight = 316.48 g/mol
| smiles = Oc1cc(cc(O)c1C/C=C(\C)CC\C=C(/C)C)CCCCC
| InChI = 1/C21H32O2/c1-5-6-7-11-18-14-20(22)19(21(23)15-18)13-12-17(4)10-8-9-16(2)3/h9,12,14-15,22-23H,5-8,10-11,13H2,1-4H3/b17-12+
| InChIKey = QXACEHWTBCFNSA-SFQUDFHCBE
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C21H32O2/c1-5-6-7-11-18-14-20(22)19(21(23)15-18)13-12-17(4)10-8-9-16(2)3/h9,12,14-15,22-23H,5-8,10-11,13H2,1-4H3/b17-12+
| StdInChI = 1S/C21H32O2/c1-5-6-7-11-18-14-20(22)19(21(23)15-18)13-12-17(4)10-8-9-16(2)3/h9,12,14-15,22-23H,5-8,10-11,13H2,1-4H3/b17-12+
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}}
}}


'''Cannabigerol''' ('''CBG''') is a non-[[psychoactive]] [[cannabinoid]] and minor constituent of [[cannabis (drug)|cannabis]].<ref name="CalapaiCardiaEsposito2022">{{cite journal | vauthors = Calapai F, Cardia L, Esposito E, Ammendolia I, Mondello C, Lo Giudice R, Gangemi S, Calapai G, Mannucci C | title = Pharmacological Aspects and Biological Effects of Cannabigerol and Its Synthetic Derivatives | journal = Evid Based Complement Alternat Med | volume = 2022 | issue = | pages = 3336516 | date = 2022 | pmid = 36397993 | pmc = 9666035 | doi = 10.1155/2022/3336516 | doi-access = free | url = }}</ref><ref name="NachnaniRaup-KonsavageVrana2021" /><ref name="GhovanlooDib-HajjGoodchild2022">{{cite journal | vauthors = Ghovanloo MR, Dib-Hajj SD, Goodchild SJ, Ruben PC, Waxman SG | title = Non-psychotropic phytocannabinoid interactions with voltage-gated sodium channels: An update on cannabidiol and cannabigerol | journal = Front Physiol | volume = 13 | issue = | pages = 1066455 | date = 2022 | pmid = 36439273 | pmc = 9691960 | doi = 10.3389/fphys.2022.1066455 | doi-access = free | url = }}</ref><ref name="MoralesReggioJagerovic2017">{{cite journal | vauthors = Morales P, Reggio PH, Jagerovic N | title = An Overview on Medicinal Chemistry of Synthetic and Natural Derivatives of Cannabidiol | journal = Frontiers in Pharmacology | volume = 8 | pages = 422 | year = 2017 | pmid = 28701957 | pmc = 5487438 | doi = 10.3389/fphar.2017.00422 | doi-access = free }}</ref><ref name="ZagoženČerenakKreft2021" /> It is one of more than 120{{nbsp}}identified cannabinoids found in the plant genus ''[[Cannabis]]''.<ref name="ElSohlyRadwanChandra2017">{{cite book | vauthors = ElSohly MA, Radwan MM, Gul W, Chandra S, Galal A | title = Phytochemistry of ''Cannabis sativa'' L. | chapter = Phytochemistry of Cannabis sativa L | volume = 103 | pages = 1–36 | year = 2017 | pmid = 28120229 | doi = 10.1007/978-3-319-45541-9_1 | isbn = 978-3-319-45539-6 | series = Progress in the Chemistry of Organic Natural Products }}</ref><ref name="TurnerWilliamsIversen2017">{{cite book | vauthors = Turner SE, Williams CM, Iversen L, Whalley BJ | chapter = Molecular Pharmacology of Phytocannabinoids | series = Progress in the Chemistry of Organic Natural Products | title = Phytocannabinoids | volume = 103 | pages = 61–101 | year = 2017 | pmid = 28120231 | doi = 10.1007/978-3-319-45541-9_3 | isbn = 978-3-319-45539-6 }}</ref> The compound is the [[decarboxylation|decarboxylated]] form of [[cannabigerolic acid]] (CBGA), the parent molecule from which other cannabinoids are [[biosynthesis|biosynthesized]].<ref name="NachnaniRaup-KonsavageVrana2021">{{cite journal | vauthors=Nachnani R, Raup-Konsavage WM, Vrana KE | title=The pharmacological case for cannabigerol | journal=The Journal of Pharmacology and Experimental Therapeutics| volume=376 | issue=2 | year=2021 | issn=0022-3565 | pmid=33168643 | doi=10.1124/jpet.120.000340 | pages=204–212| s2cid=226296897 |url=https://jpet.aspetjournals.org/content/376/2/204.long | doi-access=free }}</ref><ref name="PubChem">{{cite web |url=https://pubchem.ncbi.nlm.nih.gov/compound/Cannabigerol |title=Cannabigerol; ID 5315659 |publisher=PubChem, National Library of Medicine, US National Institutes of Health |date=2 July 2022 |access-date=7 July 2022}}</ref>
'''Cannabigerol''' ('''CBG''') is a non-psychoactive [[cannabinoid]] found in the ''[[Cannabis]]'' genus of plants. Cannabigerol is found in higher concentrations in [[hemp]] rather than in varieties of ''Cannabis'' with high [[tetrahydrocannabinol|THC]] content (the kind used as a [[drug]]).{{cn|date=May 2011}}


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.<ref name="Aizpurua-OlaizolaSoydanerÖztürk2016">{{cite journal | vauthors = Aizpurua-Olaizola O, Soydaner U, Öztürk E, Schibano D, Simsir Y, Navarro P, Etxebarria N, Usobiaga A | display-authors = 6 | title = Evolution of the Cannabinoid and Terpene Content during the Growth of Cannabis sativa Plants from Different Chemotypes | journal = Journal of Natural Products | volume = 79 | issue = 2 | pages = 324–331 | date = February 2016 | pmid = 26836472 | doi = 10.1021/acs.jnatprod.5b00949 | url = https://figshare.com/articles/journal_contribution/5028338 }}</ref> Some [[strain (biology)|strains]], however, produce larger amounts of CBG and CBGA, while having low quantities of other cannabinoids, like THC and CBD.<ref>{{Cite journal | vauthors = Zagožen M, Čerenak A, Kreft S |date=2021-09-01 |title=Cannabigerol and cannabichromene in ''Cannabis sativa'' L. |url=https://www.sciendo.com/article/10.2478/acph-2021-0021 |journal=Acta Pharmaceutica |language=en |volume=71 |issue=3 |pages=355–364 |doi=10.2478/acph-2021-0021|pmid=36654096 |s2cid=231543630 }}</ref>
Cannabigerol has been found to act as a high [[affinity_(pharmacology)|affinity]] [[a2-adrenergic receptor|α<sub>2</sub>-adrenergic receptor]] [[agonist]], moderate affinity [[5-HT1A receptor|5-HT<sub>1A</sub> receptor]] [[receptor_antagonist|antagonist]], and low affinity [[CB1 receptor|CB<sub>1</sub> receptor]] [[receptor_antagonist|antagonist]].<ref name="pmid20002104">{{cite journal | author = Cascio MG, Gauson LA, Stevenson LA, Ross RA, Pertwee R | title = Evidence that the plant cannabinoid cannabigerol is a highly potent alpha(2)-adrenoceptor agonist and moderately potent 5HT receptor antagonist | journal = British Journal of Pharmacology | volume = 159| issue = 1| pages = 129–141| year = 2009 | month = December | pmid = 20002104 | doi = 10.1111/j.1476-5381.2009.00515.x | pmc=2823359}}</ref> It also binds to the [[CB2 receptor|CB<sub>2</sub> receptor]], but whether it acts as an agonist or antagonist at this site is unknown.<ref name="pmid20002104">{{cite journal | author = Cascio MG, Gauson LA, Stevenson LA, Ross RA, Pertwee R | title = Evidence that the plant cannabinoid cannabigerol is a highly potent alpha(2)-adrenoceptor agonist and moderately potent 5HT receptor antagonist | journal = British Journal of Pharmacology | volume = 159| issue = 1| pages = 129–141| year = 2009 | month = December | pmid = 20002104 | doi = 10.1111/j.1476-5381.2009.00515.x | pmc=2823359}}</ref>


The [[pharmacodynamics]] of CBG are complex.<ref name="CalapaiCardiaEsposito2022" /><ref name="NachnaniRaup-KonsavageVrana2021" /><ref name="GhovanlooDib-HajjGoodchild2022" /> It is a relatively weak [[ligand (biochemistry)|ligand]] of the [[cannabinoid receptor]]s, where it acts as a weak [[partial agonist]].<ref name="CalapaiCardiaEsposito2022" /><ref name="NachnaniRaup-KonsavageVrana2021" /><ref name="GhovanlooDib-HajjGoodchild2022" /><ref name="JastrzabJarocka-KarpowiczSkrzydlewska2022" /> Conversely, it is a much more [[potency (pharmacology)|potent]] [[agonist]] of the [[alpha-2 adrenergic receptor|α<sub>2</sub>-adrenergic receptor]], [[receptor antagonist|antagonist]] of the [[serotonin]] [[5-HT1A receptor|5-HT<sub>1A</sub> receptor]], and antagonist of the [[transient receptor potential channel]] [[TRPM8]].<ref name="CalapaiCardiaEsposito2022" /><ref name="NachnaniRaup-KonsavageVrana2021" /><ref name="GhovanlooDib-HajjGoodchild2022" /><ref name="JastrzabJarocka-KarpowiczSkrzydlewska2022" /> CBG also has a variety of other actions that may additionally contribute to its effects.<ref name="CalapaiCardiaEsposito2022" /><ref name="NachnaniRaup-KonsavageVrana2021" /><ref name="GhovanlooDib-HajjGoodchild2022" /><ref name="ZagoženČerenakKreft2021" />


Although CBG is sold as a [[dietary supplement]], its effects and [[drug safety|safety]] for human consumption are unknown.<ref name="NachnaniRaup-KonsavageVrana2021" /> Safety concerns have been raised due to the potent activation of α<sub>2</sub>-adrenergic receptors by CBG, which may produce [[sedation]] and potentially undesirable [[cardiovascular]] effects like decreased [[heart rate]] and [[blood pressure]].<ref name="NachnaniRaup-KonsavageVrana2021" />
Cannabigerol has been shown to relieve intraoccular pressure, which may be of benefit in the treatment of [[glaucoma]].<ref>{{cite pmid|1965836}}</ref><ref>{{cite pmid|6499952}}</ref>


== See also ==
==Pharmacology==
===Pharmacodynamics===
* [[Cannabinoid]]
CBG lacks [[psychoactive]], [[wikt:cannabimimetic|cannabimimetic]], or [[psychotropic]] effects.<ref name="CalapaiCardiaEsposito2022" /><ref name="NachnaniRaup-KonsavageVrana2021" /><ref name="GhovanlooDib-HajjGoodchild2022" /><ref name="ZagoženČerenakKreft2021" /> It has been reported to reduce the psychotropic effects of [[tetrahydrocannabinol]] (THC).<ref name="CalapaiCardiaEsposito2022" /> The compound has [[analgesic]] effects.<ref name="GhovanlooDib-HajjGoodchild2022" /><ref name="Sampson2021" /><ref name="Evans1991">{{cite journal | vauthors = Evans FJ | title = Cannabinoids: the separation of central from peripheral effects on a structural basis | journal = Planta Med | volume = 57 | issue = 7 Suppl | pages = S60–S67 | date = October 1991 | pmid = 17226225 | doi = 10.1055/s-2006-960231 | url = }}</ref> [[Preclinical research]] has also found that CBG reduces [[intraocular pressure]], has [[antioxidant]], [[anti-inflammatory]], [[antineoplastic|anti-tumoral]], [[antibacterial]], and [[antifungal]] activities, and has [[antidepressant]]-like, [[anxiolytic]], [[neuromodulation|neuromodulatory]], [[neuroprotective]], [[dermatology|dermatological]], [[emesis|pro-nausea]], and [[appetite stimulant|appetite-stimulating]] effects, among others.<ref name="CalapaiCardiaEsposito2022" /><ref name="JastrzabJarocka-KarpowiczSkrzydlewska2022">{{cite journal | vauthors = Jastrząb A, Jarocka-Karpowicz I, Skrzydlewska E | title = The Origin and Biomedical Relevance of Cannabigerol | journal = Int J Mol Sci | volume = 23 | issue = 14 | date = July 2022 | page = 7929 | pmid = 35887277 | pmc = 9322760 | doi = 10.3390/ijms23147929 | doi-access = free | url = }}</ref><ref name="ZagoženČerenakKreft2021">{{cite journal | vauthors = Zagožen M, Čerenak A, Kreft S | title = Cannabigerol and cannabichromene in Cannabis sativa L | journal = Acta Pharm | volume = 71 | issue = 3 | pages = 355–364 | date = September 2021 | pmid = 36654096 | doi = 10.2478/acph-2021-0021 | url = }}</ref><ref name="Sampson2021" />
* [[Medical cannabis]]


CBG has many identified [[pharmacodynamic]] actions and its [[mechanism of action]] appears to be from interactions with multiple [[biological target|target]]s.<ref name="CalapaiCardiaEsposito2022" /><ref name="NachnaniRaup-KonsavageVrana2021" /><ref name="GhovanlooDib-HajjGoodchild2022" />
== References ==
{{Reflist}}


CBG is a weak [[ligand (biochemistry)|ligand]] of the [[cannabinoid]] [[CB1 receptor|CB<sub>1</sub>]] and [[CB2 receptor|CB<sub>2</sub> receptor]]s with [[affinity (pharmacology)|affinities]] (K<sub>i</sub>) of 380–2,600{{nbsp}}nM and 153–3,460{{nbsp}}nM, respectively.<ref name="CalapaiCardiaEsposito2022" /><ref name="NachnaniRaup-KonsavageVrana2021" /><ref name="Sampson2021">{{cite journal | vauthors = Sampson PB | title = Phytocannabinoid Pharmacology: Medicinal Properties of Cannabis sativa Constituents Aside from the "Big Two" | journal = J Nat Prod | volume = 84 | issue = 1 | pages = 142–160 | date = January 2021 | pmid = 33356248 | doi = 10.1021/acs.jnatprod.0c00965 | url = }}</ref><ref name="BindingDB">{{cite web | last=Liu | first=Tiqing | title=BindingDB BDBM50318487 CHEMBL497318::Cannabigerol | website=BindingDB | url=https://www.bindingdb.org/bind/chemsearch/marvin/MolStructure.jsp?monomerid=50318487 | access-date=14 August 2024}}</ref><ref name="MoralesHurstReggio2017" /> It is a weak [[partial agonist]] or [[receptor antagonist|antagonist]] of both of these receptors.<ref name="CalapaiCardiaEsposito2022" /><ref name="NachnaniRaup-KonsavageVrana2021" /><ref name="GhovanlooDib-HajjGoodchild2022" /> There is no information on the binding or activity of CBG at the [[GPR55]] (the potential non-homologous CB<sub>3</sub> receptor).<ref name="NachnaniRaup-KonsavageVrana2021" /><ref name="GhovanlooDib-HajjGoodchild2022" /> CBG has relatively low affinity for the cannabinoid receptors, with approximately 5-fold lower affinity for the CB<sub>1</sub> receptor and 27-fold lower affinity for the CB<sub>2</sub> receptor than THC.<ref name="JastrzabJarocka-KarpowiczSkrzydlewska2022" /> The low affinity of CBG for the CB<sub>1</sub> receptor may in part be involved in its lack of psychoactivity.<ref name="JastrzabJarocka-KarpowiczSkrzydlewska2022" />
{{Cannabinoids}}
{{Adrenergics}}
{{Serotonergics}}


CBG is a highly [[potency (pharmacology)|potent]] [[agonist]] of the [[alpha-2 adrenergic receptor|α<sub>2</sub>-adrenergic receptor]] ({{Abbrlink|EC<sub>50</sub>|half-maximal effective concentration}} = 0.2–72.8{{nbsp}}nM) and a moderately potent [[receptor antagonist|antagonist]] of the [[serotonin]] [[5-HT1A receptor|5-HT<sub>1A</sub> receptor]] (K<sub>B</sub> = 51.9{{nbsp}}nM).<ref name="NachnaniRaup-KonsavageVrana2021" /><ref name="CalapaiCardiaEsposito2022" /><ref name="CascioGausonStevenson2010">{{cite journal | vauthors = Cascio MG, Gauson LA, Stevenson LA, Ross RA, Pertwee RG | title = Evidence that the plant cannabinoid cannabigerol is a highly potent alpha2-adrenoceptor agonist and moderately potent 5HT1A receptor antagonist | journal = Br J Pharmacol | volume = 159 | issue = 1 | pages = 129–141 | date = January 2010 | pmid = 20002104 | pmc = 2823359 | doi = 10.1111/j.1476-5381.2009.00515.x | url = }}</ref> Activation of the α<sub>2</sub>-adrenergic receptor by CBG might produce effects including [[sedation]], [[dry mouth]], and decreased [[heart rate]] and [[blood pressure]].<ref name="NachnaniRaup-KonsavageVrana2021" /> This has raised [[drug safety|safety]] concerns about CBG.<ref name="NachnaniRaup-KonsavageVrana2021" /> The actions of CBG at the α<sub>2</sub>-adrenergic receptor and 5-HT<sub>1A</sub> receptor are of far greater potency than its interactions with the cannabinoid receptors and are more likely to be involved in its pharmacodynamic effects.<ref name="JastrzabJarocka-KarpowiczSkrzydlewska2022" /> These activities may specifically contribute to the analgesic and pro-nausea effects of CBG.<ref name="Sampson2021" />
[[Category:Cannabinoids]]
[[Category:Resorcinols]]
[[Category:Terpenes and terpenoids]]


The compound is a weak agonist of the [[transient receptor potential channel]]s [[TRPA1]] ({{Abbr|EC<sub>50</sub>|half-maximal effective concentration}} = 700{{nbsp}}nM), [[TRPV1]] ({{Abbr|EC<sub>50</sub>|half-maximal effective concentration}} = 1,300{{nbsp}}nM), [[TRPV2]] ({{Abbr|EC<sub>50</sub>|half-maximal effective concentration}} = 1,720{{nbsp}}nM), [[TRPV3]] ({{Abbr|EC<sub>50</sub>|half-maximal effective concentration}} = 1,000{{nbsp}}nM), and [[TRPV4]] ({{Abbr|EC<sub>50</sub>|half-maximal effective concentration}} = 5,100{{nbsp}}nM) ([[intrinsic activity|efficacy]] 18–100% at these targets) and a more potent antagonist of the transient receptor potential channel [[TRPM8]] ({{Abbrlink|IC<sub>50</sub>|half-maximal inhibitory concentration}} = 160{{nbsp}}nM).<ref name="Sampson2021" /><ref name="NachnaniRaup-KonsavageVrana2021" /><ref name="CalapaiCardiaEsposito2022" /><ref name="BindingDB" /><ref name="GhovanlooDib-HajjGoodchild2022" /> It is also a weak agonist of the [[peroxisome proliferator-activated receptor]] [[PPAR-γ]] ({{Abbr|EC<sub>50</sub>|half-maximal effective concentration}} = 1,270–15,700{{nbsp}}nM).<ref name="NachnaniRaup-KonsavageVrana2021" /><ref name="CalapaiCardiaEsposito2022" /><ref name="BindingDB" />


CBG is a [[voltage-gated sodium channel]] (VGSC) [[sodium channel blocker|blocker]] ([[Nav1.1|Na<sub>v</sub>1.1]], [[Nav1.2|Na<sub>v</sub>1.2]], [[Nav1.5|Na<sub>v</sub>1.5]], and [[Nav1.7|Na<sub>v</sub>1.7]]) and [[voltage-dependent calcium channel]] (VDCC) blocker.<ref name="GhovanlooDib-HajjGoodchild2022" /><ref name="CalapaiCardiaEsposito2022" /><ref name="GhovanlooEstacionHiberd-Rusli2022">{{cite journal | vauthors = Ghovanloo MR, Estacion M, Higerd-Rusli GP, Zhao P, Dib-Hajj S, Waxman SG | title = Inhibition of sodium conductance by cannabigerol contributes to a reduction of dorsal root ganglion neuron excitability | journal = Br J Pharmacol | volume = 179 | issue = 15 | pages = 4010–4030 | date = August 2022 | pmid = 35297036 | doi = 10.1111/bph.15833 | url = }}</ref> Inhibition of VGSCs may be involved in the analgesic effects of CBG.<ref name="GhovanlooDib-HajjGoodchild2022" />
{{nervous-system-drug-stub}}


It shows no [[enzyme inhibitor|inhibition]] of several [[endocannabinoid]]-[[metabolism|metabolizing]] [[enzyme]]s including [[fatty acid amide hydrolase]] (FAAH), [[diacylglycerol lipase]] (DGL), and [[N-acylethanolamine acid amide hydrolase|''N''-acylethanolamine acid amide hydrolase]] (NAAA).<ref name="BindingDB" /> 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).<ref name="JastrzabJarocka-KarpowiczSkrzydlewska2022" /> Aside from endocannabinoid-metabolizing enzymes, CBG is a weak inhibitor of the [[cyclooxygenase]] [[COX-1]] and [[COX-2]] enzymes (30% inhibition of each at 25,000{{nbsp}}nM).<ref name="CalapaiCardiaEsposito2022" /><ref name="JastrzabJarocka-KarpowiczSkrzydlewska2022" /> In addition, it has been found to inhibit both the [[metabolism]] and [[reuptake]] of [[anandamide]].<ref name="CalapaiCardiaEsposito2022" />
[[de:Cannabigerol]]

[[hu:Kannabigerol]]
===Pharmacokinetics===
[[pl:Kannabigerol]]
The [[pharmacokinetics]] of CBG have been studied in animals and to a lesser extent in humans.<ref name="CalapaiCardiaEsposito2022" /><ref name="JastrzabJarocka-KarpowiczSkrzydlewska2022" /> CBG is [[drug metabolism|metabolized]] in the [[liver]] by [[CYP2J2]], similarly to other cannabinoids as well as [[endocannabinoid]]s.<ref name="CalapaiCardiaEsposito2022" />

==Chemistry==
CBG is a highly [[lipophilic]] and [[hydrophobic]] compound.<ref name="GhovanlooDib-HajjGoodchild2022" /> Its predicted [[partition coefficient|log P]] ranges from 7.0 to 7.5.<ref name="PubChem" /><ref name="DrugBank">{{cite web | title=Cannabigerol: Uses, Interactions, Mechanism of Action | website=DrugBank Online | date=1 February 2019 | url=https://go.drugbank.com/drugs/DB14734 | access-date=14 August 2024}}</ref><ref name="ChemSpider">{{cite web | title=Cannabigerol | website=ChemSpider | date=14 August 2024 | url=https://www.chemspider.com/Chemical-Structure.4474921.html | access-date=14 August 2024}}</ref>

[[Synthetic compound|Synthetic]] [[chemical derivative|derivative]]s of CBG have been [[chemical synthesis|synthesized]] and studied.<ref name="CalapaiCardiaEsposito2022" /><ref name="JastrzabJarocka-KarpowiczSkrzydlewska2022" />

==History==
CBG was isolated from cannabis in 1964.<ref name="ZagoženČerenakKreft2021" />

==Society and culture==
===Legal status===
CBG is not scheduled by the [[United Nations]] [[Convention on Psychotropic Substances]].{{citation needed|date=April 2018}} 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.<ref name="fda-21">{{cite web |title=FDA Regulation of Cannabis and Cannabis-Derived Products, Including Cannabidiol (CBD) |url=https://www.fda.gov/news-events/public-health-focus/fda-regulation-cannabis-and-cannabis-derived-products-including-cannabidiol-cbd |publisher=US Food and Drug Administration |access-date=7 July 2022 |date=21 January 2021}}</ref><ref>{{Cite web|url=https://www.gpo.gov/fdsys/pkg/USCODE-2016-title21/pdf/USCODE-2016-title21-chap13-subchapI-partA-sec802.pdf|title=USC > Title 21 > Chapter 13 > Subchapter I > Part A > § 802. Definitions: (16)|date=2016|website=Government Publishing Office - US Code}}</ref>

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%.<ref>{{Cite web |last=BAG |first=Bundesamt für Gesundheit |title=Häufig gestellte Fragen (FAQ) zu Tabakersatzprodukten mit THC-armem Hanf mit CBD |url=https://www.bag.admin.ch/bag/de/home/gesetze-und-bewilligungen/gesuche-bewilligungen/gesuche-bewilligungen-im-bereich-sucht/gesetzliche-vorgaben-tabakprodukte/faq-cbd.html |access-date=2022-07-06 |website=www.bag.admin.ch |language=de}}</ref>

===Regulation===
As of 2022, the US [[Food and Drug Administration]] has issued numerous [[FDA warning letter|warning letters]] to American companies for illegally marketing cannabis supplement products,<ref name="fda-21" /> including one selling CBG products with unproven illegal claims of efficacy against the [[COVID-19 virus]] and [[inflammation]].<ref name="greenway">{{cite web | vauthors = Ashley D |date=28 March 2022 |title=Warning Letter to Greenway Herbal Products LLC; Ref. 627042 |url=https://www.fda.gov/inspections-compliance-enforcement-and-criminal-investigations/warning-letters/greenway-herbal-products-llc-627042-03282022 |access-date=7 July 2022 |publisher=Office of Compliance, Center for Drug Evaluation and Research, Food and Drug Administration}}</ref>

==Biosynthesis==
[[File:Biosynthesis of cannabigerol.jpg|thumb|230px|Biosynthesis of CBG.]]

The [[biosynthesis]] of CBG begins by loading hexanoyl-CoA onto a [[polyketide synthase]] assembly protein and subsequent [[condensation reaction|condensation]] with three molecules of [[malonyl-CoA]].<ref>{{cite journal | vauthors = Gagne SJ, Stout JM, Liu E, Boubakir Z, Clark SM, Page JE | title = Identification of olivetolic acid cyclase from Cannabis sativa reveals a unique catalytic route to plant polyketides | journal = Proceedings of the National Academy of Sciences of the United States of America | volume = 109 | issue = 31 | pages = 12811–12816 | date = July 2012 | pmid = 22802619 | pmc = 3411943 | doi = 10.1073/pnas.1200330109 | doi-access = free | bibcode = 2012PNAS..10912811G }}</ref> This [[polyketide]] is cyclized to [[olivetolic acid]] via [[olivetolic acid cyclase]], and then [[prenylation|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 [[decarboxylation|decarboxylated]] to yield CBG.<ref name="NachnaniRaup-KonsavageVrana2021" /><ref name="MoralesReggioJagerovic2017" />

==Research==
CBG is under [[basic research|laboratory research]] to determine its [[pharmacology|pharmacological]] properties and potential effects in disease conditions, with no conclusions about therapeutic effects or safety, as of 2021.<ref name="NachnaniRaup-KonsavageVrana2021" /><ref name="MoralesHurstReggio2017">{{cite book |title=Phytocannabinoids |vauthors=Morales P, Hurst DP, Reggio PH |year=2017 |isbn=978-3-319-45539-6 |series=Progress in the Chemistry of Organic Natural Products |volume=103 |pages=103–131 |chapter=Molecular Targets of the Phytocannabinoids: A Complex Picture |doi=10.1007/978-3-319-45541-9_4 |pmc=5345356 |pmid=28120232}}</ref><ref>{{cite journal |vauthors=Couch DG, Maudslay H, Doleman B, Lund JN, O'Sullivan SE |date=March 2018 |title=The Use of Cannabinoids in Colitis: A Systematic Review and Meta-Analysis |journal=Inflammatory Bowel Diseases |volume=24 |issue=4 |pages=680–697 |doi=10.1093/ibd/izy014 |pmid=29562280 |doi-access=free}}</ref> A [[clinical trial]] published in July 2024 assessed the effects of CBG on [[anxiety]], [[stress (psychological)|stress]], and [[mood (psychology)|mood]].<ref name="CuttlerStueberCooper2024">{{cite journal | vauthors = Cuttler C, Stueber A, Cooper ZD, Russo E | title = Acute effects of cannabigerol on anxiety, stress, and mood: a double-blind, placebo-controlled, crossover, field trial | journal = Sci Rep | volume = 14 | issue = 1 | pages = 16163 | date = July 2024 | pmid = 39003387 | pmc = 11246434 | doi = 10.1038/s41598-024-66879-0 | bibcode = 2024NatSR..1416163C | url = }}</ref><ref name="NeuroscienceNews2024">{{cite web | title=Cannabigerol (CBG) Reduces Anxiety and Improves Memory | website=Neuroscience News | date=31 July 2024 | url=https://neurosciencenews.com/cbg-anxiety-memory-27507/ | access-date=14 August 2024}}</ref>

==References==
{{Reflist}}

{{Cannabinoids}}
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[[Category:5-HT1A antagonists]]
[[Category:Alpha-2 adrenergic receptor agonists]]
[[Category:Calcium channel blockers]]
[[Category:CB1 receptor antagonists]]
[[Category:Phytocannabinoids]]
[[Category:Resorcinols]]
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