4'-Fluorocannabidiol (also known as PECS-101 and 4'-F-CBD, and formerly as HUF-101 and HU-474
) is a fluorinated
cannabidiol
Cannabidiol (CBD) is a phytocannabinoid discovered in 1940. It is one of 113 identified cannabinoids in cannabis plants, along with tetrahydrocannabinol (THC), and accounts for up to 40% of the plant's extract. , clinical research on CBD incl ...
derivative that has more potent
anxiolytic
An anxiolytic (; also antipanic or antianxiety agent) is a medication or other intervention that reduces anxiety. This effect is in contrast to anxiogenic agents which increase anxiety. Anxiolytic medications are used for the treatment of anxi ...
,
antidepressant
Antidepressants are a class of medication used to treat major depressive disorder, anxiety disorders, chronic pain conditions, and to help manage addictions. Common side-effects of antidepressants include dry mouth, weight gain, dizziness, hea ...
,
antipsychotic
Antipsychotics, also known as neuroleptics, are a class of Psychiatric medication, psychotropic medication primarily used to manage psychosis (including delusions, hallucinations, paranoia or disordered thought), principally in schizophrenia but ...
and anti-compulsive activity in mice compared to its parent compound.
It was first synthesized in 2016, alongside 10-fluorocannabidiol diacetate and 8,9-dihydro-7-fluorocannabidiol, which showed much weaker activity.
Synthesis
4'-Fluorocannabidiol has been synthesized from isolated cannabidiol by putting it in dry
dichloromethane
Dichloromethane (DCM or methylene chloride, methylene bichloride) is an organochlorine compound with the formula . This colorless, volatile liquid with a chloroform-like, sweet odour is widely used as a solvent. Although it is not miscible with ...
and adding
1-fluoropyridinium triflate.
See also
*
7-Hydroxycannabidiol
7-Hydroxycannabidiol (7-OH-CBD) is an active metabolite of cannabidiol, generated in the body from cannabidiol by the action of the enzyme CYP2C19. While methods have been developed for its synthetic production, and measurement of levels in the ...
*
8,9-Dihydrocannabidiol
8,9-Dihydrocannabidiol (also known as H2CBD, DiHydroCBD, Delta-1-H2CBD, or Delta-1-DiHydroCBD) is a synthetic cannabinoid that is closely related to cannabidiol (CBD) itself.
Pharmacology
It may have certain advantages over CBD, in that it is f ...
*
Abnormal cannabidiol
Abnormal cannabidiol (Abn-CBD) is a synthetic regioisomer of cannabidiol, which unlike most other cannabinoids produces vasodilator effects, lowers blood pressure, and induces cell migration, cell proliferation and mitogen-activated protein kinase ...
*
Cannabinoids
Cannabinoids () are several structural classes of compounds found in the cannabis plant primarily and most animal organisms (although insects lack such receptors) or as synthetic compounds. The most notable cannabinoid is the phytocannabinoid tet ...
*
Cannabinoid receptor
Cannabinoid receptors, located throughout the body, are part of the endocannabinoid system a class of cell membrane receptors in the G protein-coupled receptor superfamily. As is typical of G protein-coupled receptors, the cannabinoid recepto ...
s
*
HU-331
HU-331 is a quinone anticarcinogenic drug synthesized from cannabidiol, a cannabinoid in the ''Cannabis sativa'' plant. It showed a great efficacy against oncogenic human cells. HU-331 does not cause arrest in cell cycle, cell apoptosis or caspas ...
*
KLS-13019
KLS-13019 is a cannabidiol derivative that has been modified on the side chain to improve solubility and tissue penetration properties. It was developed and patented by Neuropathix subsidiary Kannalife and found to be 50x more potent than canna ...
*
O-1602
O-1602 is a synthetic compound most closely related to abnormal cannabidiol, and more distantly related in structure to cannabinoid drugs such as THC. O-1602 does not bind to the classical cannabinoid receptors CB1 or CB2 with any significant aff ...
*
O-1918
O-1918 is a synthetic compound related to cannabidiol, which is an antagonist at two former orphan receptors GPR18 and GPR55, that appear to be related to the cannabinoid receptors. O-1918 is used in the study of these receptors, which have been ...
References
Cannabinoids
Antidepressants
Antipsychotics
Anxiolytics
Pain
Fluoroarenes
2,6-Dihydroxybiphenyls
Cyclohexenes
Substances discovered in the 2010s
{{cannabinoid-stub