U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry RACEMIC
Molecular Formula C10H13NO2.ClH
Molecular Weight 215.677
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

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

SMILES

Cl.NCC(CC(O)=O)C1=CC=CC=C1

InChI

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

HIDE SMILES / InChI

Molecular Formula C10H13NO2
Molecular Weight 179.2157
Charge 0
Count
Stereochemistry RACEMIC
Additional Stereochemistry No
Defined Stereocenters 0 / 1
E/Z Centers 0
Optical Activity ( + / - )

Molecular Formula ClH
Molecular Weight 36.461
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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
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
[Effect of the GABA derivative phenibut on learning].
2005
[The effect of GABA derivative phenibut on defensive conditioning and internal inhibition].
2006 Mar-Apr
Neurochemical mechanisms of the dorsal pallidum in the antiaversive effects of anxiolytics in various models of anxiety.
2006 Sep
[Effect of GABA receptor agonist phenibut on behavior and respiration of rabbits in the negative emotional situation].
2007 Jul-Aug
[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
The effects of agonists of ionotropic GABA(A) and metabotropic GABA(B) receptors on learning.
2009 May
Nootropic and antiamnestic effects of tenoten (pediatric formulation) in immature rat pups.
2009 Sep
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.
Substance Class Chemical
Created
by admin
on Sat Dec 16 07:51:13 UTC 2023
Edited
by admin
on Sat Dec 16 07:51:13 UTC 2023
Record UNII
625240H2LN
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
4-AMINO-3-PHENYLBUTYRIC ACID HYDROCHLORIDE
MI  
Systematic Name English
HYDROCINNAMIC ACID, .BETA.-(AMINOMETHYL)-, HYDROCHLORIDE
Common Name English
.BETA.-PHENYL-GABA HYDROCHLORIDE
Common Name English
.GAMMA.-AMINO-.BETA.-PHENYLBUTYRIC ACID HYDROCHLORIDE
Systematic Name English
4-Amino-3-phenylbutyric acid hydrochloride [WHO-DD]
Common Name English
4-AMINO-3-PHENYLBUTANOIC ACID HYDROCHLORIDE, (±)-
Common Name English
4-AMINO-3-PHENYLBUTYRIC ACID HYDROCHLORIDE [MI]
Common Name English
BENZENEPROPANOIC ACID, .BETA.-(AMINOMETHYL)-, HYDROCHLORIDE
Common Name English
Code System Code Type Description
PUBCHEM
18288
Created by admin on Sat Dec 16 07:51:14 UTC 2023 , Edited by admin on Sat Dec 16 07:51:14 UTC 2023
PRIMARY
MERCK INDEX
m1730
Created by admin on Sat Dec 16 07:51:14 UTC 2023 , Edited by admin on Sat Dec 16 07:51:14 UTC 2023
PRIMARY Merck Index
SMS_ID
300000017632
Created by admin on Sat Dec 16 07:51:14 UTC 2023 , Edited by admin on Sat Dec 16 07:51:14 UTC 2023
PRIMARY
FDA UNII
625240H2LN
Created by admin on Sat Dec 16 07:51:14 UTC 2023 , Edited by admin on Sat Dec 16 07:51:14 UTC 2023
PRIMARY
CAS
3060-41-1
Created by admin on Sat Dec 16 07:51:14 UTC 2023 , Edited by admin on Sat Dec 16 07:51:14 UTC 2023
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE