4'-Fluorocannabidiol
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| Formula | C21H29FO2 |
| Molar mass | 332.459 g·mol−1 |
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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
[edit]4'-Fluorocannabidiol has been synthesized from isolated cannabidiol by putting it in dry dichloromethane and adding 1-fluoropyridinium triflate.[2]
See also
[edit]- 7-Hydroxycannabidiol
- 8,9-Dihydrocannabidiol
- Abnormal cannabidiol
- Cannabinoids
- Cannabinoid receptors
- HU-331
- KLS-13019
- O-1602
- O-1918
References
[edit]- ^ 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.
- ^ 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.
- ^ 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.
- ^ 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.
- ^ 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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