Page last updated: 2024-12-05

4-amino-3-phenylbutyric acid

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

Description

4-amino-3-phenylbutyric acid: phenyl deriv of GABA; RN given refers to cpd without isomeric designation; structure [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID14113
CHEMBL ID315818
CHEBI ID136039
SCHEMBL ID340838
MeSH IDM0053046

Synonyms (67)

Synonym
1078-21-3
phenygam
dl-4-amino-3-phenylbutanoic acid
phenigamma
CHEMBL315818
beta-phenyl-gamma-aminobutyric acid
brn 2804903
phenibut
butyric acid, 4-amino-3-phenyl-
beta-phenyl-gamma-aminobutyrate
einecs 214-079-6
phenylgamma
phenigam
4-amino-3-phenylbutanoic acid
4-amino-3-phenylbutyric acid
pgaba
phgaba
fenigama
beta-(aminomethyl)hydrocinnamic acid
beta-(aminomethyl)benzenepropanoic acid
phenigama
benzenepropanoic acid, beta-(aminomethyl)-
phenylgam
fenibut
OPREA1_183000
OPREA1_381119
STK182861
CHEBI:136039
AKOS000555914
A8650
(s)-4-amino-3-phenylbutanoicacid
BBL000576
t2m58d6la8 ,
unii-t2m58d6la8
4-14-00-01723 (beilstein handbook reference)
FT-0600356
D10509
S4892
AKOS016347357
SCHEMBL340838
.beta.-phenyl-.gamma.-aminobutyric acid
phenibut [who-dd]
(+/-)-.beta.-phenyl-gaba
.beta.-(aminomethyl)hydrocinnamic acid
(+/-)-fenibut
.beta.-(aminomethyl)benzenepropanoic acid
4-amino-3-phenylbutyric acid [mi]
benzenepropanoic acid, .beta.-(aminomethyl)-
DAFOCGYVTAOKAJ-UHFFFAOYSA-N
3-amino-2-phenylpropanecarboxylic acid
4-amino-3-pheny-butyric acid
3-[3-(aminomethyl)phenyl]propionic acid
mfcd00456233
EX-A734
phenibut; fenibut
GS-3145
3-phenyl-4-aminobutanoic acid
DTXSID70870838
Q419559
EN300-110013
DB13455
BCP10710
HMS3886K05
CCG-266416
D96082
benzenepropanoic acid, b-(aminomethyl)-
Z1255487817

Research Excerpts

Toxicity

ExcerptReferenceRelevance
" To gather information on prevalence of use, desired effects and/or adverse effects, we searched grey literature (online drug discussion forums) and medical literature (PubMed and abstracts from selected International Toxicology conferences)."( Phenibut (4-amino-3-phenyl-butyric acid): Availability, prevalence of use, desired effects and acute toxicity.
Archer, JR; Dargan, PI; Owen, DR; Wood, DM, 2016
)
0.43
" According to the grey literature, phenibut is taken for its anxiolytic and euphoric properties, with tolerance and withdrawal syndromes commonly reported adverse effects."( Phenibut (4-amino-3-phenyl-butyric acid): Availability, prevalence of use, desired effects and acute toxicity.
Archer, JR; Dargan, PI; Owen, DR; Wood, DM, 2016
)
0.43
" Its desired and adverse effects appear similar to other gamma-aminobutyric acid receptor agonists."( Phenibut (4-amino-3-phenyl-butyric acid): Availability, prevalence of use, desired effects and acute toxicity.
Archer, JR; Dargan, PI; Owen, DR; Wood, DM, 2016
)
0.43

Bioavailability

ExcerptReferenceRelevance
" Absolute bioavailability was 64%."( Study of the absolute bioavailability of citrocard, a new GABA derivative.
Lebedeva, SA; Perfilova, VN; Ryabukha, AF; Smirnova, LA; Suchkov, EA; Tyurenkov, IN, 2013
)
0.39

Dosage Studied

ExcerptRelevanceReference
" Patients of the first group received adaptol in dosage 1000 mg daily and patients of the second group received noofen in dosage 500 mg daily."( [Asthenic disorders in children and their differentiated treatment].
Anisimova, TI; Bondarchuk, IL; Chutko, LS; Iakovenko, EA; Nikishena, IS; Sergeev, AV; Surushkina, SI, 2014
)
0.4
"To study impulsivity in adolescents with attention deficit hyperactivity disorder (ADHD) and evaluate the efficacy of noophen in dosage 500 mg daily for 45 days in the treatment of this disorder."( [Impulsivity in adolescents with attention deficit hyperactivity disorder].
Anisimova, TI; Chutko, LS; Kropotov, YD; Sergeev, AV; Surushkina, EY; Yakovenko, EA,
)
0.13
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (2)

ClassDescription
organonitrogen compoundAny heteroorganic entity containing at least one carbon-nitrogen bond.
organooxygen compoundAn organochalcogen compound containing at least one carbon-oxygen bond.
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Protein Targets (2)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Gamma-aminobutyric acid type B receptor subunit 2Homo sapiens (human)Ki177.00006.00006.00006.0000AID1237981
Gamma-aminobutyric acid type B receptor subunit 1Homo sapiens (human)Ki177.00006.00006.00006.0000AID1237981
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (19)

Processvia Protein(s)Taxonomy
G protein-coupled receptor signaling pathwayGamma-aminobutyric acid type B receptor subunit 2Homo sapiens (human)
adenylate cyclase-inhibiting G protein-coupled receptor signaling pathwayGamma-aminobutyric acid type B receptor subunit 2Homo sapiens (human)
negative regulation of adenylate cyclase activityGamma-aminobutyric acid type B receptor subunit 2Homo sapiens (human)
gamma-aminobutyric acid signaling pathwayGamma-aminobutyric acid type B receptor subunit 2Homo sapiens (human)
chemical synaptic transmissionGamma-aminobutyric acid type B receptor subunit 2Homo sapiens (human)
synaptic transmission, GABAergicGamma-aminobutyric acid type B receptor subunit 2Homo sapiens (human)
neuron-glial cell signalingGamma-aminobutyric acid type B receptor subunit 2Homo sapiens (human)
osteoblast differentiationGamma-aminobutyric acid type B receptor subunit 1Homo sapiens (human)
adenylate cyclase-inhibiting G protein-coupled receptor signaling pathwayGamma-aminobutyric acid type B receptor subunit 1Homo sapiens (human)
gamma-aminobutyric acid signaling pathwayGamma-aminobutyric acid type B receptor subunit 1Homo sapiens (human)
negative regulation of cell population proliferationGamma-aminobutyric acid type B receptor subunit 1Homo sapiens (human)
positive regulation of glutamate secretionGamma-aminobutyric acid type B receptor subunit 1Homo sapiens (human)
negative regulation of gamma-aminobutyric acid secretionGamma-aminobutyric acid type B receptor subunit 1Homo sapiens (human)
negative regulation of epinephrine secretionGamma-aminobutyric acid type B receptor subunit 1Homo sapiens (human)
negative regulation of dopamine secretionGamma-aminobutyric acid type B receptor subunit 1Homo sapiens (human)
response to nicotineGamma-aminobutyric acid type B receptor subunit 1Homo sapiens (human)
response to ethanolGamma-aminobutyric acid type B receptor subunit 1Homo sapiens (human)
negative regulation of synaptic transmissionGamma-aminobutyric acid type B receptor subunit 1Homo sapiens (human)
synaptic transmission, GABAergicGamma-aminobutyric acid type B receptor subunit 1Homo sapiens (human)
regulation of postsynaptic membrane potentialGamma-aminobutyric acid type B receptor subunit 1Homo sapiens (human)
positive regulation of growth hormone secretionGamma-aminobutyric acid type B receptor subunit 1Homo sapiens (human)
regulation of presynaptic membrane potentialGamma-aminobutyric acid type B receptor subunit 1Homo sapiens (human)
neuron-glial cell signalingGamma-aminobutyric acid type B receptor subunit 1Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (7)

Processvia Protein(s)Taxonomy
G protein-coupled GABA receptor activityGamma-aminobutyric acid type B receptor subunit 2Homo sapiens (human)
protein bindingGamma-aminobutyric acid type B receptor subunit 2Homo sapiens (human)
protein heterodimerization activityGamma-aminobutyric acid type B receptor subunit 2Homo sapiens (human)
transmembrane signaling receptor activityGamma-aminobutyric acid type B receptor subunit 2Homo sapiens (human)
G protein-coupled GABA receptor activityGamma-aminobutyric acid type B receptor subunit 1Homo sapiens (human)
G protein-coupled GABA receptor activityGamma-aminobutyric acid type B receptor subunit 1Homo sapiens (human)
protein bindingGamma-aminobutyric acid type B receptor subunit 1Homo sapiens (human)
protein heterodimerization activityGamma-aminobutyric acid type B receptor subunit 1Homo sapiens (human)
G protein-coupled neurotransmitter receptor activity involved in regulation of postsynaptic membrane potentialGamma-aminobutyric acid type B receptor subunit 1Homo sapiens (human)
G protein-coupled neurotransmitter receptor activity involved in regulation of presynaptic membrane potentialGamma-aminobutyric acid type B receptor subunit 1Homo sapiens (human)
extracellular matrix protein bindingGamma-aminobutyric acid type B receptor subunit 1Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (19)

Processvia Protein(s)Taxonomy
cytoplasmGamma-aminobutyric acid type B receptor subunit 2Homo sapiens (human)
plasma membraneGamma-aminobutyric acid type B receptor subunit 2Homo sapiens (human)
neuron projectionGamma-aminobutyric acid type B receptor subunit 2Homo sapiens (human)
postsynaptic membraneGamma-aminobutyric acid type B receptor subunit 2Homo sapiens (human)
G protein-coupled GABA receptor complexGamma-aminobutyric acid type B receptor subunit 2Homo sapiens (human)
G protein-coupled receptor heterodimeric complexGamma-aminobutyric acid type B receptor subunit 2Homo sapiens (human)
GABA receptor complexGamma-aminobutyric acid type B receptor subunit 2Homo sapiens (human)
extracellular spaceGamma-aminobutyric acid type B receptor subunit 1Homo sapiens (human)
endoplasmic reticulum membraneGamma-aminobutyric acid type B receptor subunit 1Homo sapiens (human)
plasma membraneGamma-aminobutyric acid type B receptor subunit 1Homo sapiens (human)
synaptic vesicleGamma-aminobutyric acid type B receptor subunit 1Homo sapiens (human)
axolemmaGamma-aminobutyric acid type B receptor subunit 1Homo sapiens (human)
mitochondrial membraneGamma-aminobutyric acid type B receptor subunit 1Homo sapiens (human)
presynaptic membraneGamma-aminobutyric acid type B receptor subunit 1Homo sapiens (human)
neuronal cell bodyGamma-aminobutyric acid type B receptor subunit 1Homo sapiens (human)
dendritic spineGamma-aminobutyric acid type B receptor subunit 1Homo sapiens (human)
dendritic shaftGamma-aminobutyric acid type B receptor subunit 1Homo sapiens (human)
postsynaptic membraneGamma-aminobutyric acid type B receptor subunit 1Homo sapiens (human)
Schaffer collateral - CA1 synapseGamma-aminobutyric acid type B receptor subunit 1Homo sapiens (human)
glutamatergic synapseGamma-aminobutyric acid type B receptor subunit 1Homo sapiens (human)
GABA-ergic synapseGamma-aminobutyric acid type B receptor subunit 1Homo sapiens (human)
G protein-coupled GABA receptor complexGamma-aminobutyric acid type B receptor subunit 1Homo sapiens (human)
G protein-coupled receptor heterodimeric complexGamma-aminobutyric acid type B receptor subunit 1Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (1)

Assay IDTitleYearJournalArticle
AID1237981Displacement of [3H]CGP54626 from GABA-B receptor (unknown origin) by radioligand binding assay2015Journal of medicinal chemistry, Aug-27, Volume: 58, Issue:16
Activation of the γ-Aminobutyric Acid Type B (GABA(B)) Receptor by Agonists and Positive Allosteric Modulators.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (125)

TimeframeStudies, This Drug (%)All Drugs %
pre-199027 (21.60)18.7374
1990's12 (9.60)18.2507
2000's17 (13.60)29.6817
2010's52 (41.60)24.3611
2020's17 (13.60)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 27.27

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be moderate demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index27.27 (24.57)
Research Supply Index5.36 (2.92)
Research Growth Index4.90 (4.65)
Search Engine Demand Index47.92 (26.88)
Search Engine Supply Index2.91 (0.95)

This Compound (27.27)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials11 (5.50%)5.53%
Reviews11 (5.50%)6.00%
Case Studies21 (10.50%)4.05%
Observational1 (0.50%)0.25%
Other156 (78.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]