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4'-Fluorocannabidiol

From Wikipedia, the free encyclopedia
Chemical compound
Pharmaceutical compound
4'-Fluorocannabidiol
Legal status
Legal status
Identifiers
  • 4-Fluoro-2-[(1R,6R)-3-methyl-6-(prop-1-en-2-yl)cyclohex-2-en-1-yl]-5-pentylbenzene-1,3-diol
CAS Number
PubChemCID
ChemSpider
UNII
CompTox Dashboard(EPA)
Chemical and physical data
FormulaC21H29FO2
Molar mass332.459 g·mol−1
3D model (JSmol)
  • CCCCCC1=CC(=C(C(=C1F)O)[C@@H]2C=C(CC[C@H]2C(=C)C)C)O
  • InChI=1S/C21H29FO2/c1-5-6-7-8-15-12-18(23)19(21(24)20(15)22)17-11-14(4)9-10-16(17)13(2)3/h11-12,16-17,23-24H,2,5-10H2,1,3-4H3/t16-,17+/m0/s1
  • Key:OGZHPYIVJQZXQS-DLBZAZTESA-N

4'-Fluorocannabidiol (also known asPECS-101 and4'-F-CBD, and formerly asHUF-101 andHU-474[1]) is a fluorinatedcannabidiol derivative that has more potentanxiolytic,antidepressant,antipsychotic and anti-compulsive activity in mice compared to its parent compound.[2][3][4][5] It was first synthesized in 2016, alongside 10-fluorocannabidiol diacetate and 8,9-dihydro-7-fluorocannabidiol, which showed much weaker activity.[2]

Synthesis

[edit]

4'-Fluorocannabidiol has been synthesized from isolated cannabidiol by putting it in drydichloromethane and adding1-fluoropyridinium triflate.[2]

See also

[edit]

References

[edit]
  1. ^Stollenwerk TM, Pollock S, Hillard CJ (2 September 2021)."Contribution of the Adenosine 2A Receptor to Behavioral Effects of Tetrahydrocannabinol, Cannabidiol and PECS-101".Molecules.26 (17): 5354.doi:10.3390/molecules26175354.PMC 8434367.PMID 34500787.
  2. ^abcBreuer A, Haj CG, Fogaça MV, Gomes FV, Silva NR, Pedrazzi JF, et al. (14 July 2016)."Fluorinated Cannabidiol Derivatives: Enhancement of Activity in Mice Models Predictive of Anxiolytic, Antidepressant and Antipsychotic Effects".PLOS ONE.11 (7): e0158779.Bibcode:2016PLoSO..1158779B.doi:10.1371/journal.pone.0158779.PMC 4945002.PMID 27416026.
  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. ^Silva NR, Gomes FV, Fonseca MD, Mechoulam R, Breuer A, Cunha TM, Guimarães FS (October 2017). "Antinociceptive effects of HUF-101, a fluorinated cannabidiol derivative".Progress in Neuro-Psychopharmacology & Biological Psychiatry.79 (Pt B):369–377.doi:10.1016/j.pnpbp.2017.07.012.PMID 28720466.S2CID 21626587.
  5. ^Perez M, Cartarozzi LP, Chiarotto GB, Oliveira SA, Guimarães FS, Oliveira AL (September 2018). "Neuronal preservation and reactive gliosis attenuation following neonatal sciatic nerve axotomy by a fluorinated cannabidiol derivative".Neuropharmacology.140:201–208.doi:10.1016/j.neuropharm.2018.08.009.PMID 30096328.S2CID 51956774.
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