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Cannabimovone
1-[(1R,2R,3S,4R)-3-(2,6-dihydroxy-4-pentylphenyl)-2-hydroxy-4-prop-1-en-2-ylcyclopentyl]ethanone
PubChem CID ChemSpider 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 (International Ed. in English ed.). 55 (25): 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 .
Cannabinoids
Phytocannabinoids
Cannabichromenes Cannabicyclols Cannabidiols Cannabielsoins Cannabigerols Cannabinols and cannabinodiols Cannabitriols Delta-8-tetrahydrocannabinols Delta-9-tetrahydrocannabinols
Delta-9-THC (THC)
THCH
THCP
THCV
Miscellaneous cannabinoids Active metabolites
Endocannabinoids
Arachidonoyl ethanolamide (AEA; anandamide)
2-Arachidonoylglycerol (2-AG)
2-Arachidonyl glyceryl ether (2-AGE; noladin ether)
2-Oleoylglycerol (2-OG)
N-Arachidonoyl dopamine (NADA)
N-Arachidonylglycine (NAGly)
N-Arachidonoyl serotonin (AA-5-HT)
Docosatetraenoylethanolamide (DEA)
Lysophosphatidylinositol (LPI)
Oleamide
Oleoylethanolamide (OEA)
Palmitoylethanolamide (PEA)
RVD-Hpα
Stearoylethanolamide (SEA)
O-Arachidonoyl ethanolamine (O-AEA; virodhamine)
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
A-796,260
A-834,735
FUB-144
UR-144
XLR-11
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Tetramethylcyclo- propylindoles Others
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See also: Cannabinoid receptor modulators (cannabinoids by pharmacology)
List of: AM cannabinoids
JWH cannabinoids
Designer drugs § Synthetic cannabimimetics
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