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Details

Stereochemistry RACEMIC
Molecular Formula C10H13NO2
Molecular Weight 179.2161
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of 4-AMINO-3-PHENYLBUTYRIC ACID

SMILES

c1ccc(cc1)C(CC(=O)O)CN

InChI

InChIKey=DAFOCGYVTAOKAJ-UHFFFAOYSA-N
InChI=1S/C10H13NO2/c11-7-9(6-10(12)13)8-4-2-1-3-5-8/h1-5,9H,6-7,11H2,(H,12,13)

HIDE SMILES / InChI
Phenibut (beta-phenyl-gamma-aminobutyric acid or 4-amino-3-phenylbutyric acid) is a neuropsychotropic drug that was discovered and introduced into clinical practice in Russia in the 1960s. It has anxiolytic and nootropic (cognition enhancing) effects. It acts as a GABA-mimetic, primarily at GABA(B) receptors. Pharmacological activity of racemic phenibut relies on R-phenibut and this correlates to the binding affinity of enantiomers of phenibut to the GABAB receptor. In addition R-phenibut binds to the α2-δ subunit of voltage-dependent calcium channels. It is highly effective in treating anxiety, post-traumatic stress disorder, depression, asthenia, insomnia, alcoholism, stuttering, and vestibular disorders. It also improves mental performance (attention, memory, speed and accuracy of sensory-motor reactions), physical performance, reduces sleep disorders as well as movement and speech disorders.

Originator

Sources: Khaunma RA. Tranquillizing effects of beta-phenyl-gamma-aminobutyric acid (“Phenigama”). Byull Eksp Biol Med 1964;1:54–58
Curator's Comment:: Phenibut (beta-phenyl-gamma-aminobutyric acid, beta-phenyl-GABA) was synthesized by Perekalin and his associates at the Department of Organic Chemistry of the Herzen Pe-dagogic Institute in St. Petersburg, Russia. https://www.ncbi.nlm.nih.gov/pubmed/11830761

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
PHENIBUT

Approved Use

Asthenic and Anxious-Neurotic States, Worry, Anxiety, Fear Sleep Disorders Tiredness Improve Memory, Cognition, Mood
Primary
PHENIBUT

Approved Use

Asthenic and Anxious-Neurotic States, Worry, Anxiety, Fear Sleep Disorders Tiredness Improve Memory, Cognition, Mood
Primary
PHENIBUT

Approved Use

Asthenic and Anxious-Neurotic States, Worry, Anxiety, Fear Sleep Disorders Tiredness Improve Memory, Cognition, Mood
PubMed

PubMed

TitleDatePubMed
[Antiabstinent action of fenibut and baclofen on a model of abstinence induced by the benzodiazepine receptor antagonist CGS 8216 in rats receiving diazepam].
1987 Jun
[Experimental study of the antiepileptic activity of fenibut and its combinations with sodium valproate and aminooxyacetic acid].
1988 May-Jun
[Monoamine, GABA, and glutamergic mechanisms of the anterior hypothalamus in anti-aversive effects of sedative and selective drugs in various models of anxiety].
2001 Mar-Apr
[Neurochemical characteristics of the ventromedial hypothalamus and anti-aversive effects of anxiolytic agents in various anxiety models].
2001 Sep
Phenibut (beta-phenyl-GABA): a tranquilizer and nootropic drug.
2001 Winter
[Anti-arrhythmic properties of GABA and GABA-ergic system activators].
2002 Jan-Feb
Cyclic GMP protein kinase activity is reduced in thyroxine-induced hypertrophic cardiac myocytes.
2003 Dec
[Cardiac effects of fenibut in development of experimental chronic renal insufficiency].
2003 Jul-Aug
Neurochemical characteristics of the ventromedial hypothalamus in mediating the antiaversive effects of anxiolytics in different models of anxiety.
2003 Mar
[Autonomic cardiovascular regulation in patients with tics and Tourette syndrome].
2005
[Effect of the GABA derivative phenibut on learning].
2005
[Neurochemical mechanisms of dorsal pallidum in antiadverse effects of anxiolytics of different models of anxiety].
2005 Jul
[Effect of phenibut on the behavior of experimental animals under conditions of voluntary chronic alcoholism].
2005 May-Jun
[Peculiarities of nootropic effect of phenibut].
2006
[Effect of phenibut on the respiratory arrest caused by serotonin].
2006 Jan-Feb
[Neurochemical features of the ventral pallidum in realization of the antiaversive effects of anxiolytics in different models of anxiety].
2006 Jan-Feb
[Cardioprotective effect of GABA derivatives in acute alcohol intoxication].
2006 Jul-Aug
[The effect of GABA derivative phenibut on defensive conditioning and internal inhibition].
2006 Mar-Apr
[Comparative evaluation of the neuroprotective activity of phenibut and piracetam under experimental cerebral ischemia conditions in rats].
2006 May-Jun
Neurochemical mechanisms of the dorsal pallidum in the antiaversive effects of anxiolytics in various models of anxiety.
2006 Sep
[Correction of cardiotoxic effect of chronic alcoholic intoxication by GABA-ergic compounds].
2007
Effect of citrocard on functional reserves of the heart under conditions of chronic stress.
2007 Jul
[Effect of GABA receptor agonist phenibut on behavior and respiration of rabbits in the negative emotional situation].
2007 Jul-Aug
Effect of Citrocard on functional activity of cardiomyocyte mitochondria during chronic alcohol intoxication.
2007 Mar
Quantitative analysis of phenibut in rat brain tissue extracts by liquid chromatography-tandem mass spectrometry.
2008 Dec
Effects of the GABA receptor agonist phenibut on behavior and respiration in rabbits in emotionally negative situations.
2008 Jul
Comparative pharmacological activity of optical isomers of phenibut.
2008 Mar 31
[Effect of phenibut on the content of monoamines, their metabolites, and neurotransmitter amino acids in rat brain structures].
2009 Jan-Feb
[Effect of phenibut on interhemispheric transmission in the rat brain].
2009 Jan-Feb
[Effects of aminalon, fenibut, and picamilon on the typological parameters of cerebral hemodynamics in swimmers with dysadaptation syndrome].
2009 Jul-Aug
Comparative study of immunocorrective activity of phenibut and its organic salts in experimental immunodeficiency.
2009 May
The effects of agonists of ionotropic GABA(A) and metabotropic GABA(B) receptors on learning.
2009 May
The influence of agonists of GABA(A) and GABA(B) receptors on the formation of the defensive and inhibitory conditioned reflexes.
2009 Nov-Dec
[Efficiency of noophen in heroin addiction].
2009 Oct-Dec
Nootropic and antiamnestic effects of tenoten (pediatric formulation) in immature rat pups.
2009 Sep
[Influence of GABA agonist phenibut on the neuronal activity and interaction in hippocampus and neocortex in emotionally negative situations].
2009 Sep
[Effects of phenibut on parameters of cerebral hemodynamics in swimmers with dysadaptation syndrome and various types of systemic hemodynamics].
2010 Aug
[Interhemisphere asymmetry of hippocampus and neocortex in correlates of active and passive behavioural strategy in negative emotional situations].
2010 Dec
[Comparative study of immunomodulating properties of phenibut and gammoxin].
2010 Dec
[Changes in the psycho-emotional state under conditions of suppressed immunogenesis, the correction of the disorders with GABA-positive means].
2010 Feb
[Immune-regulating effect of phenibut under lipopolysaccharide-induced immune stress conditions].
2010 May
Paired-pulse inhibition in the auditory cortex in Parkinson's disease and its dependence on clinical characteristics of the patients.
2010 Nov 1
Withdrawal symptoms after Internet purchase of phenibut (β-phenyl-γ-aminobutyric acid HCl).
2010 Oct
Patents

Patents

Sample Use Guides

Initial dose is 250-500 mg (1-2 pills) 3 times a day. Maximum single dose: 750 mg, for patients over 60 years: 500 mg. The course of treatment is 2-3 weeks. If necessary, the course of treatment can be prolonged to 4-6 weeks. Patients, who have somnolence or other central nervous system disturbances during administration of Phenibut, should be careful about driving.
Route of Administration: Oral
In Vitro Use Guide
It has been established in experiments on the isolated spinal cord of 7-14-day-old rats that the GABAB-mimetic phenibut (10-100 uM) elicits a slow-developing depolarization of motoneurons, suppression of spontaneous activity and polysynaptic reflex discharges of motoneurons, recorded from the ventral roots.
Name Type Language
4-AMINO-3-PHENYLBUTYRIC ACID
MI  
Systematic Name English
.BETA.-PHENYL-.GAMMA.-AMINOBUTYRIC ACID
Systematic Name English
PHENIGAMMA
Brand Name English
(+/-)-FENIBUT
Common Name English
DL-4-AMINO-3-PHENYLBUTANOIC ACID
Common Name English
(+/-)-.BETA.-PHENYL-GABA
Common Name English
PHGABA
Common Name English
PHENYGAM
Brand Name English
FENIBUT
Brand Name English
.BETA.-(AMINOMETHYL)HYDROCINNAMIC ACID
Systematic Name English
4-AMINO-3-PHENYLBUTYRIC ACID [MI]
Common Name English
4-AMINO-3-PHENYLBUTANOIC ACID
Systematic Name English
PHENIBUT [WHO-DD]
Common Name English
.BETA.-(AMINOMETHYL)BENZENEPROPANOIC ACID
Systematic Name English
PHENIBUT
WHO-DD  
Brand Name English
Classification Tree Code System Code
WHO-ATC N06BX22
Created by admin on Fri Jun 25 20:51:06 UTC 2021 , Edited by admin on Fri Jun 25 20:51:06 UTC 2021
DSLD 2945 (Number of products:14)
Created by admin on Fri Jun 25 20:51:06 UTC 2021 , Edited by admin on Fri Jun 25 20:51:06 UTC 2021
WHO-VATC QN06BX22
Created by admin on Fri Jun 25 20:51:06 UTC 2021 , Edited by admin on Fri Jun 25 20:51:06 UTC 2021
Code System Code Type Description
PUBCHEM
14113
Created by admin on Fri Jun 25 20:51:06 UTC 2021 , Edited by admin on Fri Jun 25 20:51:06 UTC 2021
PRIMARY
FDA UNII
T2M58D6LA8
Created by admin on Fri Jun 25 20:51:06 UTC 2021 , Edited by admin on Fri Jun 25 20:51:06 UTC 2021
PRIMARY
CAS
1078-21-3
Created by admin on Fri Jun 25 20:51:06 UTC 2021 , Edited by admin on Fri Jun 25 20:51:06 UTC 2021
PRIMARY
DRUG BANK
DB13455
Created by admin on Fri Jun 25 20:51:06 UTC 2021 , Edited by admin on Fri Jun 25 20:51:06 UTC 2021
PRIMARY
ECHA (EC/EINECS)
214-079-6
Created by admin on Fri Jun 25 20:51:06 UTC 2021 , Edited by admin on Fri Jun 25 20:51:06 UTC 2021
PRIMARY
ChEMBL
CHEMBL315818
Created by admin on Fri Jun 25 20:51:06 UTC 2021 , Edited by admin on Fri Jun 25 20:51:06 UTC 2021
PRIMARY
WIKIPEDIA
PHENIBUT
Created by admin on Fri Jun 25 20:51:06 UTC 2021 , Edited by admin on Fri Jun 25 20:51:06 UTC 2021
PRIMARY
MERCK INDEX
M1730
Created by admin on Fri Jun 25 20:51:06 UTC 2021 , Edited by admin on Fri Jun 25 20:51:06 UTC 2021
PRIMARY Merck Index
DRUG CENTRAL
4863
Created by admin on Fri Jun 25 20:51:06 UTC 2021 , Edited by admin on Fri Jun 25 20:51:06 UTC 2021
PRIMARY
MESH
C008842
Created by admin on Fri Jun 25 20:51:06 UTC 2021 , Edited by admin on Fri Jun 25 20:51:06 UTC 2021
PRIMARY
EVMPD
SUB35018
Created by admin on Fri Jun 25 20:51:06 UTC 2021 , Edited by admin on Fri Jun 25 20:51:06 UTC 2021
PRIMARY