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Chemical compound
4'-Fluorocannabidiol
Legal status
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 )
Formula C 21 H 29 F O 2
Molar mass 332.459 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]
4'-Fluorocannabidiol has been synthesized from isolated cannabidiol by putting it in dry
dichloromethane and adding
1-fluoropyridinium triflate .
[2]
^ 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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comparison )
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