Details
| Stereochemistry | RACEMIC |
| Molecular Formula | C10H13NO2 |
| Molecular Weight | 179.2157 |
| Optical Activity | ( + / - ) |
| Defined Stereocenters | 0 / 1 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
NCC(CC(O)=O)C1=CC=CC=C1
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)
| 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 | ( + / - ) |
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
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
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
| 177.0 µM [Ki] | |||
Target ID: CHEMBL3420 |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Primary | PHENIBUT Approved UseAsthenic and Anxious-Neurotic States, Worry, Anxiety, Fear
Sleep Disorders
Tiredness
Improve Memory, Cognition, Mood |
|||
| Primary | PHENIBUT Approved UseAsthenic and Anxious-Neurotic States, Worry, Anxiety, Fear
Sleep Disorders
Tiredness
Improve Memory, Cognition, Mood |
|||
| Primary | PHENIBUT Approved UseAsthenic and Anxious-Neurotic States, Worry, Anxiety, Fear
Sleep Disorders
Tiredness
Improve Memory, Cognition, Mood |
Doses
| Dose | Population | Adverse events |
|---|---|---|
1.5 g 4 times / day multiple, oral Overdose Dose: 1.5 g, 4 times / day Route: oral Route: multiple Dose: 1.5 g, 4 times / day Sources: |
unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M Food Status: UNKNOWN Sources: |
Disc. AE: Consciousness loss... AEs leading to discontinuation/dose reduction: Consciousness loss Sources: |
30 g single, oral Overdose |
unknown, ADULT Health Status: unknown Age Group: ADULT Sex: M Food Status: UNKNOWN Sources: |
Disc. AE: Agitation, Somnolence... AEs leading to discontinuation/dose reduction: Agitation Sources: Somnolence Dystonia |
500 mg 2 times / day multiple, oral Recommended Dose: 500 mg, 2 times / day Route: oral Route: multiple Dose: 500 mg, 2 times / day Sources: |
unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: |
AEs
| AE | Significance | Dose | Population |
|---|---|---|---|
| Consciousness loss | Disc. AE | 1.5 g 4 times / day multiple, oral Overdose Dose: 1.5 g, 4 times / day Route: oral Route: multiple Dose: 1.5 g, 4 times / day Sources: |
unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M Food Status: UNKNOWN Sources: |
| Agitation | Disc. AE | 30 g single, oral Overdose |
unknown, ADULT Health Status: unknown Age Group: ADULT Sex: M Food Status: UNKNOWN Sources: |
| Dystonia | Disc. AE | 30 g single, oral Overdose |
unknown, ADULT Health Status: unknown Age Group: ADULT Sex: M Food Status: UNKNOWN Sources: |
| Somnolence | Disc. AE | 30 g single, oral Overdose |
unknown, ADULT Health Status: unknown Age Group: ADULT Sex: M Food Status: UNKNOWN Sources: |
PubMed
| Title | Date | PubMed |
|---|---|---|
| [Interhemisphere asymmetry of hippocampus and neocortex in correlates of active and passive behavioural strategy in negative emotional situations]. | 2010-12 |
|
| [Comparative study of immunomodulating properties of phenibut and gammoxin]. | 2010-12 |
|
| Paired-pulse inhibition in the auditory cortex in Parkinson's disease and its dependence on clinical characteristics of the patients. | 2010-11-01 |
|
| Withdrawal symptoms after Internet purchase of phenibut (β-phenyl-γ-aminobutyric acid HCl). | 2010-10 |
|
| [Effects of phenibut on parameters of cerebral hemodynamics in swimmers with dysadaptation syndrome and various types of systemic hemodynamics]. | 2010-08 |
|
| [Efficiency of noophen in heroin addiction]. | 2010-05-12 |
|
| [Immune-regulating effect of phenibut under lipopolysaccharide-induced immune stress conditions]. | 2010-05 |
|
| The influence of agonists of GABA(A) and GABA(B) receptors on the formation of the defensive and inhibitory conditioned reflexes. | 2010-02-23 |
|
| [Changes in the psycho-emotional state under conditions of suppressed immunogenesis, the correction of the disorders with GABA-positive means]. | 2010-02 |
|
| [Effects of aminalon, fenibut, and picamilon on the typological parameters of cerebral hemodynamics in swimmers with dysadaptation syndrome]. | 2009-10-07 |
|
| Nootropic and antiamnestic effects of tenoten (pediatric formulation) in immature rat pups. | 2009-09 |
|
| [Influence of GABA agonist phenibut on the neuronal activity and interaction in hippocampus and neocortex in emotionally negative situations]. | 2009-09 |
|
| Comparative study of immunocorrective activity of phenibut and its organic salts in experimental immunodeficiency. | 2009-05 |
|
| The effects of agonists of ionotropic GABA(A) and metabotropic GABA(B) receptors on learning. | 2009-05 |
|
| [Effect of phenibut on the content of monoamines, their metabolites, and neurotransmitter amino acids in rat brain structures]. | 2009-04-02 |
|
| [Effect of phenibut on interhemispheric transmission in the rat brain]. | 2009-04-02 |
|
| Quantitative analysis of phenibut in rat brain tissue extracts by liquid chromatography-tandem mass spectrometry. | 2008-12 |
|
| Effects of the GABA receptor agonist phenibut on behavior and respiration in rabbits in emotionally negative situations. | 2008-07 |
|
| Comparative pharmacological activity of optical isomers of phenibut. | 2008-03-31 |
|
| [Effect of GABA receptor agonist phenibut on behavior and respiration of rabbits in the negative emotional situation]. | 2007-10-20 |
|
| Effect of citrocard on functional reserves of the heart under conditions of chronic stress. | 2007-07 |
|
| Effect of Citrocard on functional activity of cardiomyocyte mitochondria during chronic alcohol intoxication. | 2007-03 |
|
| [Correction of cardiotoxic effect of chronic alcoholic intoxication by GABA-ergic compounds]. | 2007 |
|
| [Cardioprotective effect of GABA derivatives in acute alcohol intoxication]. | 2006-09-26 |
|
| Neurochemical mechanisms of the dorsal pallidum in the antiaversive effects of anxiolytics in various models of anxiety. | 2006-09 |
|
| [Comparative evaluation of the neuroprotective activity of phenibut and piracetam under experimental cerebral ischemia conditions in rats]. | 2006-08-02 |
|
| [The effect of GABA derivative phenibut on defensive conditioning and internal inhibition]. | 2006-06-08 |
|
| [Effect of phenibut on the respiratory arrest caused by serotonin]. | 2006-04-04 |
|
| [Neurochemical features of the ventral pallidum in realization of the antiaversive effects of anxiolytics in different models of anxiety]. | 2006-04-04 |
|
| [Peculiarities of nootropic effect of phenibut]. | 2006 |
|
| [Effect of phenibut on the behavior of experimental animals under conditions of voluntary chronic alcoholism]. | 2005-07-29 |
|
| [Neurochemical mechanisms of dorsal pallidum in antiadverse effects of anxiolytics of different models of anxiety]. | 2005-07 |
|
| [Autonomic cardiovascular regulation in patients with tics and Tourette syndrome]. | 2005 |
|
| [Effect of the GABA derivative phenibut on learning]. | 2005 |
|
| Cyclic GMP protein kinase activity is reduced in thyroxine-induced hypertrophic cardiac myocytes. | 2003-12 |
|
| [Cardiac effects of fenibut in development of experimental chronic renal insufficiency]. | 2003-10-16 |
|
| Neurochemical characteristics of the ventromedial hypothalamus in mediating the antiaversive effects of anxiolytics in different models of anxiety. | 2003-03 |
|
| [Anti-arrhythmic properties of GABA and GABA-ergic system activators]. | 2002-05-25 |
|
| [Monoamine, GABA, and glutamergic mechanisms of the anterior hypothalamus in anti-aversive effects of sedative and selective drugs in various models of anxiety]. | 2001-09-11 |
|
| [Neurochemical characteristics of the ventromedial hypothalamus and anti-aversive effects of anxiolytic agents in various anxiety models]. | 2001-09 |
|
| Phenibut (beta-phenyl-GABA): a tranquilizer and nootropic drug. | 2001 |
|
| [Experimental study of the antiepileptic activity of fenibut and its combinations with sodium valproate and aminooxyacetic acid]. | 1988-05-01 |
|
| [Antiabstinent action of fenibut and baclofen on a model of abstinence induced by the benzodiazepine receptor antagonist CGS 8216 in rats receiving diazepam]. | 1987-06 |
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
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
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admin
on
Edited
Mon Mar 31 21:43:39 GMT 2025
by
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on
Mon Mar 31 21:43:39 GMT 2025
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| Record UNII |
T2M58D6LA8
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| Record Status |
Validated (UNII)
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| Record Version |
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WHO-ATC |
N06BX22
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DSLD |
2945 (Number of products:14)
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WHO-VATC |
QN06BX22
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WIKIPEDIA |
Designer-drugs-Phenibut
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14113
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T2M58D6LA8
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1078-21-3
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DB13455
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214-079-6
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CHEMBL315818
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DTXSID70870838
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PHENIBUT
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m1730
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4863
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C008842
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11885
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100000128219
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SUB35018
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TARGET -> AGONIST |
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SALT/SOLVATE -> PARENT |
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