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Cannabimovone

From Wikipedia, the free encyclopedia
Chemical compound
Pharmaceutical compound
Cannabimovone
Identifiers
  • 1-[(1R,2R,3S,4R)-3-(2,6-dihydroxy-4-pentylphenyl)-2-hydroxy-4-prop-1-en-2-ylcyclopentyl]ethanone
CAS Number
PubChemCID
ChemSpider
CompTox Dashboard(EPA)
Chemical and physical data
FormulaC21H30O4
Molar mass346.467 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 aphytocannabinoid first isolated from a non-psychoactive strain ofCannabis sativa in 2010, which is thought to be a rearrangement product ofcannabidiol. It lacks affinity forcannabinoid receptors, but acts as an agonist at bothTRPV1 andPPARγ.[1][2][3][4]

See also

[edit]

References

[edit]
  1. ^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.
  2. ^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.
  3. ^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.
  4. ^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
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AllostericCBRTooltip Cannabinoid receptorligands
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