4'-Fluorocannabidiol

4'-Fluorocannabidiol (also known as HUF-101 and 4'-F-CBD) is a fluorinated cannabidiol derivative that has more potent anxiolytic, antidepressant, antipsychotic and anti-compulsive activity in mice compared to its parent compound.[1] It was first synthesized in 2016, alongside 10-fluorocannabidiol diacetate and 8,9-dihydro-7-fluorocannabidiol.[1]

4'-Fluorocannabidiol

Legal status
Legal status	CA: Schedule II
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	1619228-89-5
PubChem CID	76285390
ChemSpider	58191436
Chemical and physical data
Formula	C21H29FO2
Molar mass	332.459 g·mol^−1
3D model (JSmol)	Interactive image
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.[1]

See also

• Abnormal cannabidiol
• Cannabidiol
• Cannabinoids
• Cannabinoid receptors
• HU-331
• KLS-13019
• O-1602
• O-1918

References

1. 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.