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4'-Fluorocannabidiol

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
PubChem CID
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 as PECS-101 and 4'-F-CBD, and formerly as HUF-101 and HU-474[1]) is a fluorinated cannabidiol derivative that has more potent anxiolytic, 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

4'-Fluorocannabidiol has been synthesized from isolated cannabidiol by putting it in dry dichloromethane and adding 1-fluoropyridinium triflate.[2]

See also

References

  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. ^ a b c Breuer 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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