Cannabigerol

Cannabigerol

Systematic (IUPAC) name
2-[(2E)-3,7-dimethylocta-2,6-dienyl]-5-pentyl-benzene-1,3-diol
Identifiers
CAS Number	25654-31-3 N
ATC code	none
PubChem	CID: 5315659
ChemSpider	4474921 Y
ChEMBL	CHEMBL497318 Y
Chemical data
Formula	C21H32O2
Molecular mass	316.48 g/mol
SMILES Oc1cc(cc(O)c1C/C=C(\C)CC\C=C(/C)C)CCCCC
InChI InChI=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+ Y Key:QXACEHWTBCFNSA-SFQUDFHCSA-N Y
NY (what is this?)  (verify)

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 cultivated for high tetrahydrocannabinol (THC) content and their corresponding psychoactive properties.

Cannabigerol has been found to act as a high affinity α₂-adrenergic receptor agonist, moderate affinity 5-HT_1A receptor antagonist, and low affinity CB₁ receptor antagonist. It also binds to the CB₂ receptor, but whether it acts as an agonist or antagonist at this site is unknown.

Chemistry

It has two E/Z isomers.

Uses

Cannabigerol has been shown to relieve intraocular pressure, which may be of benefit in the treatment of glaucoma. It can also be used to treat inflammatory bowel disease. CBG can also inhibit the uptake of GABA in the brain, which can decrease anxiety and muscle tension.

Legal status

CBG is not scheduled by Convention on Psychotropic Substances.

United States

CBG is not scheduled at the federal level in the United States.

Biosynthesis

The biosynthesis of CBG begins loading a hexanoyl CoA onto a ketide synthetase assembly protein and subsequent condensation with three malonyl CoA molecules. This polyketide is cyclized to olivetolic acid via an olivetolic cyclase, and then prenylated with a 10 carbon isoprenoid using Geranyldiphosphate (GPP) and an aromatic prenyltransferase protein to biosynthesize a precursor to CBG, cannabichomenic acid (CBCA). CBCA is also a precursor to many cannabinoid compounds, including tetrahydrocannabinolic acid, or THCA. Finally, CBCA is cyclized into cannabigerolic acid (CBGA) using a cannabichromenic acid synthetase, and decarboxylation yields cannabigerol.

See also

• Cannabinoid
• Medical cannabis