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
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
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.
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 |
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Target ID: CHEMBL2111463 |
177.0 µM [Ki] | ||
Target ID: CHEMBL3420 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26234470 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Primary | PHENIBUT Approved UseAsthenic and Anxious-Neurotic States, Worry, Anxiety, Fear
Sleep Disorders
Tiredness
Improve Memory, Cognition, Mood |
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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 |
PubMed
Title | Date | PubMed |
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Cyclic GMP protein kinase activity is reduced in thyroxine-induced hypertrophic cardiac myocytes. | 2003 Dec |
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[Cardiac effects of fenibut in development of experimental chronic renal insufficiency]. | 2003 Jul-Aug |
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[Effect of the GABA derivative phenibut on learning]. | 2005 |
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[The effect of GABA derivative phenibut on defensive conditioning and internal inhibition]. | 2006 Mar-Apr |
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Neurochemical mechanisms of the dorsal pallidum in the antiaversive effects of anxiolytics in various models of anxiety. | 2006 Sep |
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[Effect of GABA receptor agonist phenibut on behavior and respiration of rabbits in the negative emotional situation]. | 2007 Jul-Aug |
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[Effect of phenibut on interhemispheric transmission in the rat brain]. | 2009 Jan-Feb |
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[Effects of aminalon, fenibut, and picamilon on the typological parameters of cerebral hemodynamics in swimmers with dysadaptation syndrome]. | 2009 Jul-Aug |
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The effects of agonists of ionotropic GABA(A) and metabotropic GABA(B) receptors on learning. | 2009 May |
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Nootropic and antiamnestic effects of tenoten (pediatric formulation) in immature rat pups. | 2009 Sep |
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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/2861865
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
Edited
Sat Dec 16 07:51:13 UTC 2023
by
admin
on
Sat Dec 16 07:51:13 UTC 2023
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Record UNII |
625240H2LN
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Record Status |
Validated (UNII)
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Record Version |
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m1730
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300000017632
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625240H2LN
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3060-41-1
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admin on Sat Dec 16 07:51:14 UTC 2023 , Edited by admin on Sat Dec 16 07:51:14 UTC 2023
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Related Record | Type | Details | ||
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PARENT -> SALT/SOLVATE |
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