Cannabimovone

Cannabimovone
Identifiers
	IUPAC name 1-[(1R,2R,3S,4R)-3-(2,6-dihydroxy-4-pentylphenyl)-2-hydroxy-4-prop-1-en-2-ylcyclopentyl]ethanone;
CAS Number	1227939-59-4;
PubChem CID	134955841;
ChemSpider	75573942;
CompTox Dashboard (EPA)	DTXSID401337105 ;
Chemical and physical data
Formula	C21H30O4
Molar mass	346.467 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES 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 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]

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.

[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.

[pmid27119910-2] 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.

[pmid28701957-3] 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.

[pmid32138197-4] 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.

[1]

[2]

[3]

[4]

See also

References