4'-Fluorocannabidiol

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
Chemical and physical data
Formula	C21H29FO2
Molar mass	332.46 g·mol^−1
3D model (Jmol)	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

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]

Synthesis

4'-fluoro-cannabidiol was synthesized from isolated cannabidiol by putting it in dry dichloromethane and adding 1-fluoropyridinium triflate.^[1]

See also

• 2-Isopropyl-5-methyl-1-(2,6-dihydroxy-4-nonylphenyl)cyclohex-1-ene
• Abnormal cannabidiol
• Cannabinodiol
• Cannabinoids
• Cannabinoid receptors
• HU-331
• O-1602
• O-1918

References

1. Breuer, Aviva; Haj, Christeene G.; Fogaça, Manoela V.; Gomes, Felipe V.; Silva, Nicole Rodrigues; Pedrazzi, João Francisco; Bel, Elaine A. Del; Hallak, Jaime C.; Crippa, José A.; Zuardi, Antonio W.; Mechoulam, Raphael; Guimarães, Francisco S. (14 July 2016). "Fluorinated Cannabidiol Derivatives: Enhancement of Activity in Mice Models Predictive of Anxiolytic, Antidepressant and Antipsychotic Effects". PLOS ONE. 11 (7): e0158779. ISSN 1932-6203. PMC 4945002. PMID 27416026.