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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

Description

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.

CNS Activity

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency
177.0 µM [Ki]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
PHENIBUT
Primary
PHENIBUT
Primary
PHENIBUT

T1/2

ValueDoseCo-administeredAnalytePopulation
5.3 h
250 mg single, oral
4-AMINO-3-PHENYLBUTYRIC ACID plasma
Homo sapiens

Doses

AEs

PubMed

Patents

Sample Use Guides

In Vivo Use Guide
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.