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4-Fluorophenibut

From Wikipedia, the free encyclopedia

GABAB receptor agonist and phenibut analogue

Pharmaceutical compound

4-Fluorophenibut
Clinical data

Other names	CGP-11130; β-(4-Fluorophenyl)-γ-aminobutyric acid; β-(4-Fluorophenyl)-GABA; Baflofen; Fluorophenibut; F-Phenibut; Fluoribut
Routes of administration	By mouth
Identifiers
IUPAC name 4-Amino-3-(4-fluorophenyl)butanoic acid
CAS Number	52237-19-1
PubChemCID	103611
ChemSpider	93547
UNII	6DAU7M5P3D
CompTox Dashboard(EPA)	DTXSID00966612
Chemical and physical data
Formula	C₁₀H₁₂FNO₂
Molar mass	197.209 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES C1=CC(=CC=C1C(CC(=O)O)CN)F
InChI InChI=1S/C10H12FNO2/c11-9-3-1-7(2-4-9)8(6-12)5-10(13)14/h1-4,8H,5-6,12H2,(H,13,14) Key:QWHXHLDNSXLAPX-UHFFFAOYSA-N

4-Fluorophenibut (developmental code nameCGP-11130; also known asβ-(4-fluorophenyl)-γ-aminobutyric acid orβ-(4-fluorophenyl)-GABA) is aGABA_B receptor agonist which was never marketed.^[1] It isselective for the GABA_B receptor over theGABA_A receptor (IC₅₀ = 1.70 μM and > 100 μM, respectively).^[1] The drug is aGABA analogue and is closely related tobaclofen (β-(4-chlorophenyl)-GABA),tolibut (β-(4-methylphenyl)-GABA), andphenibut (β-phenyl-GABA).^[1] It is less potent as a GABA_B receptor agonist than baclofen but more potent than phenibut.^[1]

The substance is sometimes referred to as4F-phenibut,F-phenibut, orbaflofen, and colloquially asfluorobut.

Legal status

F-Phenibut is a prohibited substance in Lithuania^[2] and Hungary.^[3]

References

^^a ^b ^c ^dBowery NG, Hill DR, Hudson AL (1983)."Characteristics of GABAB receptor binding sites on rat whole brain synaptic membranes".Br. J. Pharmacol.78 (1):191–206.doi:10.1111/j.1476-5381.1983.tb09380.x.PMC 2044790.PMID 6297646.
^"RINKOS RIBOJIMO PRIEMONĖS FENIBUTUI!".ntakd.lrv.lt (in Lithuanian). Retrieved2020-01-27.
^MAGYARORSZÁG HIVATALOS LAPJA. Retrieved 2021-04-28.

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GABA receptor modulators

GABA_ATooltip γ-Aminobutyric acid A receptor

Positive modulators (abridged; seehere for a full list):α-EMTBL
Alcohols (e.g.,drinking alcohol,2M2B)
Anabolic steroids
Avermectins (e.g.,ivermectin)
Barbiturates (e.g.,phenobarbital)
Benzodiazepines (e.g.,diazepam)
Bromide compounds (e.g.,potassium bromide)
Carbamates (e.g.,meprobamate)
Carbamazepine
Chloralose
Chlormezanone
Clomethiazole
Dihydroergolines (e.g.,ergoloid (dihydroergotoxine))
Etazepine
Etifoxine
Fenamates (e.g.,mefenamic acid)
Flavonoids (e.g.,apigenin,hispidulin)
Fluoxetine
Flupirtine
Imidazoles (e.g.,etomidate)
Kava constituents (e.g.,kavain)
Lanthanum
Loreclezole
Monastrol
Neuroactive steroids (e.g.,allopregnanolone,cholesterol,THDOC)
Niacin
Niacinamide
Nonbenzodiazepines (e.g.,β-carbolines (e.g.,abecarnil),cyclopyrrolones (e.g.,zopiclone),imidazopyridines (e.g.,zolpidem),pyrazolopyrimidines (e.g.,zaleplon))
Norfluoxetine
Petrichloral
Phenols (e.g.,propofol)
Phenytoin
Piperidinediones (e.g.,glutethimide)
Propanidid
Pyrazolopyridines (e.g.,etazolate)
Quinazolinones (e.g.,methaqualone)
Retigabine (ezogabine)
ROD-188
Skullcap constituents (e.g.,baicalin)
Stiripentol
Sulfonylalkanes (e.g.,sulfonmethane (sulfonal))
Topiramate
Valerian constituents (e.g.,valerenic acid)
Volatiles/gases (e.g.,chloral hydrate,chloroform,diethyl ether,paraldehyde,sevoflurane)

GABA_A-ρTooltip γ-Aminobutyric acid A-rho receptor

Negative modulators:5α-Dihydroprogesterone
Bilobalide
Loreclezole
Picrotoxin (picrotin,picrotoxinin)
Pregnanolone
ROD-188
THDOC
Zinc

GABA_BTooltip γ-Aminobutyric acid B receptor

Negative modulators:Compound 14

See also: Receptor/signaling modulators; GABA_A receptor positive modulators; GABA metabolism/transport modulators

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