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Chemical compound
Cannabimovone
1-[(1R,2R,3S,4R)-3-(2,6-dihydroxy-4-pentylphenyl)-2-hydroxy-4-prop-1-en-2-ylcyclopentyl]ethanone
PubChem
CID
ChemSpider
CompTox Dashboard (
EPA )
Formula C 21 H 30 O 4
Molar mass 346.467 g·mol−1 3D model (
JSmol )
CCCCCC1=CC(=C(C(=C1)O)[C@@H]2[C@@H](C[C@H]([C@@H]2O)C(=O)C)C(=C)C)O
InChI=1S/C21H30O4/c1-5-6-7-8-14-9-17(23)20(18(24)10-14)19-15(12(2)3)11-16(13(4)22)21(19)25/h9-10,15-16,19,21,23-25H,2,5-8,11H2,1,3-4H3/t15-,16-,19-,21-/m0/s1
Key:YNKVBFQBHSCXGQ-UGJIMAENSA-N
Cannabimovone (CBM ) is a
phytocannabinoid first isolated from a non-psychoactive strain of
Cannabis sativa in 2010, which is thought to be a rearrangement product of
cannabidiol . It lacks affinity for
cannabinoid receptors , but acts as an agonist at both
TRPV1 and
PPARγ .
[1]
[2]
[3]
[4]
See also
References
^ Taglialatela-Scafati O, Pagani A, Scala F, De Petrocellis L, Di Marzo V, Grassi G, Appendino G (2010). "Cannabimovone, a Cannabinoid with a Rearranged Terpenoid Skeleton from Hemp". European Journal of Organic Chemistry . 2010 (11): 2067–2072.
doi :
10.1002/ejoc.200901464 .
^ Carreras J, Kirillova MS, Echavarren AM (June 2016).
"Synthesis of (-)-Cannabimovone and Structural Reassignment of Anhydrocannabimovone through Gold(I)-Catalyzed Cycloisomerization" . Angewandte Chemie . 55 (25) (International Ed. in English ed.): 7121–5.
doi :
10.1002/anie.201601834 .
PMC
5053274 .
PMID
27119910 .
^ Morales P, Reggio PH, Jagerovic N (2017).
"An Overview on Medicinal Chemistry of Synthetic and Natural Derivatives of Cannabidiol" . Frontiers in Pharmacology . 8 : 422.
doi :
10.3389/fphar.2017.00422 .
PMC
5487438 .
PMID
28701957 .
^ Iannotti FA, De Maio F, Panza E, Appendino G, Taglialatela-Scafati O, De Petrocellis L, Amodeo P, Vitale RM (March 2020).
"Identification and Characterization of Cannabimovone, a Cannabinoid from Cannabis sativa, as a Novel PPARγ Agonist via a Combined Computational and Functional Study" . Molecules (Basel, Switzerland) . 25 (5): 1119.
doi :
10.3390/molecules25051119 .
PMC
7179127 .
PMID
32138197 .
Phytocannabinoids (
comparison )
Cannabibutols Cannabichromenes Cannabicyclols Cannabidiols Cannabielsoins Cannabigerols Cannabiphorols Cannabinols Cannabitriols Cannabivarins Delta-8-tetrahydrocannabinols Delta-9-tetrahydrocannabinols Delta-10-Tetrahydrocannabinols Miscellaneous cannabinoids Active metabolites
Endocannabinoids
Synthetic cannabinoid receptor agonists / neocannabinoids
Classical cannabinoids (dibenzopyrans) Non-classical cannabinoids Adamantoylindoles Benzimidazoles Benzoylindoles Cyclohexylphenols
Eicosanoids
Hydrocarbons Indazole carboxamides Indazole-3- carboxamides Indole-3-carboxamides Indole-3-carboxylates Naphthoylindazoles
Naphthoylindoles Naphthoylpyrroles Naphthylmethylindenes Naphthylmethylindoles Phenylacetylindoles Pyrazolecarboxamides Pyrrolobenzoxazines Quinolinyl esters Tetramethylcyclo- propanoylindazoles Tetramethylcyclo- propanoylindoles Tetramethylcyclo- propylindoles Others
Allosteric
CBR Tooltip Cannabinoid receptor
ligands
Endocannabinoid enhancers (inactivation inhibitors)
Anticannabinoids (antagonists/inverse agonists/antibodies)