4'-Fluorocannabidiol

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]

4'-Fluorocannabidiol
Legal status
Legal status
Identifiers
IUPAC name
  • 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
Chemical and physical data
FormulaC21H29FO2
Molar mass332.459 g·mol−1
3D model (JSmol)
SMILES
  • CCCCCC1=CC(=C(C(=C1F)O)[C@@H]2C=C(CC[C@H]2C(=C)C)C)O
InChI
  • 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

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.
  2. 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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