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

Details

Stereochemistry RACEMIC
Molecular Formula C4H9NO3
Molecular Weight 119.1192
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of .GAMMA.-AMINO-.BETA.-HYDROXYBUTYRIC ACID

SMILES

NCC(O)CC(O)=O

InChI

InChIKey=YQGDEPYYFWUPGO-UHFFFAOYSA-N
InChI=1S/C4H9NO3/c5-2-3(6)1-4(7)8/h3,6H,1-2,5H2,(H,7,8)

HIDE SMILES / InChI
Molecular Formula C4H9NO3
Molecular Weight 119.1192
Charge 0
Count
Stereochemistry RACEMIC
Additional Stereochemistry No
Defined Stereocenters 0 / 1
E/Z Centers 0
Optical Activity ( + / - )

Description
Curator's Comment: description was created based on several sources, including: https://www.antiaging-systems.com/38-aminohydroxybutyric-acid-gabob-buxamin https://www.ncbi.nlm.nih.gov/pubmed/2854014 https://en.wikipedia.org/wiki/Gamma-Amino-beta-hydroxybutyric_acid

4-Amino-3-hydroxybutanoic acid (GABOB) is an endogenous ligand found in the central nervous system in mammals. γ-Amino-β-hydroxybutyric acid is a derivative of the neurotransmitter GABA. It has been claimed to be of value in neurological disorders and to have an antihypertensive effect. γ-Amino-β-hydroxybutyric acid can help overcome stress and anxiety, improve learning and boost memory function. It is also known to increase growth hormone levels, which help the body heal and rejuvenate itself. There are no reported side effects of γ-Amino-β-hydroxybutyric acid when taken at therapeutic dosages. At high dosages, some slight drowsiness may occur. Adverse effects have included dizziness and anorexia also.

CNS Activity

Originator

Tomita, M.
1
Sources: DOI: 10.1515/bchm2.1923.124.3-6.253

Approval Year

Unknown
139594
Targets

Targets

Primary TargetPharmacologyConditionPotency
Agonist
2678
 19.1 µM [EC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Approved
8429
GABOMADE

Approved Use

Adjuvant therapy of primary and secondary syndromes comitial and convulsive states the most varied etiology, especially in children.

Launch Date

1.13512323E12
Primary
Approved
8429
GABOMADE

Approved Use

Indicated for the mental retardation treatment

Launch Date

1.13512323E12
Primary
Approved
8429
GABOMADE

Approved Use

Indicated for the headache treatment

Launch Date

1.13512323E12
PubMed

PubMed

TitleDatePubMed
The inhibitory action of beta-hydroxy-gamma-aminobutyric acid upon the seizure following stimulation of the motor cortex of the dog.
1959 Mar 12
[Gamibetal (gamma-amino-beta-hydroxybutyric acid--GABOB) in the treatment of epilepsy].
1967 Mar-Apr
Patents

Patents

ES 278780
1
FR 1348105
1
JP 58 772
1
JP 62 12264
1
JP 63 24365
1

Sample Use Guides

In Vivo Use Guide
Anxiety or stress: take 1 × 500mg tablet, or 2 × 250mg daily. For epilepsy take 2 × 500mg tablets twice daily.
Route of Administration: Oral
In Vitro Use Guide
Upon spinal ganglion cells, to which the GABOB is added in 0.5 mg/cc, is effective for maintenance and differentiation of nerve cells.
Substance Class Chemical
Created
by admin
on Fri Dec 15 18:19:53 UTC 2023
Edited
by admin
on Fri Dec 15 18:19:53 UTC 2023
Record UNII
1ZHM019FLD
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
.GAMMA.-AMINO-.BETA.-HYDROXYBUTYRIC ACID
JAN  
Systematic Name English
GAMIBETAL
Brand Name English
4-AMINO-3-HYDROXYBUTYRIC ACID [INCI]
Common Name English
BUTANOIC ACID, 4-AMINO-3-HYDROXY-, (±)-
Common Name English
GAMMA-AMINO-BETA-HYDROXYBUTYRIC ACID
Systematic Name English
GABOB
Common Name English
4-AMINO-3-HYDROXYBUTYRIC ACID
INCI   MART.   MI   WHO-DD  
INCI  
Official Name English
GAMMA-AMINO-BETA-HYDROXYBUTYRIC ACID [JAN]
Common Name English
NSC-40244
Code English
BUKSAMIN
Common Name English
(±)-4-AMINO-3-HYDROXYBUTYRIC ACID
Systematic Name English
4-AMINO-3-HYDROXYBUTYRIC ACID [MI]
Common Name English
GABOMADE
Brand Name English
4-amino-3-hydroxybutyric acid [WHO-DD]
Common Name English
BUTYRIC ACID, 4-AMINO-3-HYDROXY-, DL-
Common Name English
4-AMINO-3-HYDROXYBUTYRIC ACID [MART.]
Common Name English
Code System Code Type Description
CAS
352-21-6
Created by admin on Fri Dec 15 18:19:53 UTC 2023 , Edited by admin on Fri Dec 15 18:19:53 UTC 2023
SUPERSEDED
CHEBI
16080
Created by admin on Fri Dec 15 18:19:53 UTC 2023 , Edited by admin on Fri Dec 15 18:19:53 UTC 2023
PRIMARY
SMS_ID
100000087596
Created by admin on Fri Dec 15 18:19:53 UTC 2023 , Edited by admin on Fri Dec 15 18:19:53 UTC 2023
PRIMARY
ECHA (EC/EINECS)
213-106-9
Created by admin on Fri Dec 15 18:19:53 UTC 2023 , Edited by admin on Fri Dec 15 18:19:53 UTC 2023
PRIMARY
WIKIPEDIA
gamma-Amino-beta-hydroxybutyric acid
Created by admin on Fri Dec 15 18:19:53 UTC 2023 , Edited by admin on Fri Dec 15 18:19:53 UTC 2023
PRIMARY
FDA UNII
1ZHM019FLD
Created by admin on Fri Dec 15 18:19:53 UTC 2023 , Edited by admin on Fri Dec 15 18:19:53 UTC 2023
PRIMARY
MESH
C004480
Created by admin on Fri Dec 15 18:19:53 UTC 2023 , Edited by admin on Fri Dec 15 18:19:53 UTC 2023
PRIMARY
ECHA (EC/EINECS)
206-518-5
Created by admin on Fri Dec 15 18:19:53 UTC 2023 , Edited by admin on Fri Dec 15 18:19:53 UTC 2023
ALTERNATIVE
EPA CompTox
DTXSID1045877
Created by admin on Fri Dec 15 18:19:53 UTC 2023 , Edited by admin on Fri Dec 15 18:19:53 UTC 2023
PRIMARY
EVMPD
SUB23341
Created by admin on Fri Dec 15 18:19:53 UTC 2023 , Edited by admin on Fri Dec 15 18:19:53 UTC 2023
PRIMARY
PUBCHEM
2149
Created by admin on Fri Dec 15 18:19:53 UTC 2023 , Edited by admin on Fri Dec 15 18:19:53 UTC 2023
PRIMARY
NSC
40244
Created by admin on Fri Dec 15 18:19:53 UTC 2023 , Edited by admin on Fri Dec 15 18:19:53 UTC 2023
PRIMARY
ChEMBL
CHEMBL93515
Created by admin on Fri Dec 15 18:19:53 UTC 2023 , Edited by admin on Fri Dec 15 18:19:53 UTC 2023
PRIMARY
MERCK INDEX
m1711
Created by admin on Fri Dec 15 18:19:53 UTC 2023 , Edited by admin on Fri Dec 15 18:19:53 UTC 2023
PRIMARY Merck Index
CAS
924-49-2
Created by admin on Fri Dec 15 18:19:53 UTC 2023 , Edited by admin on Fri Dec 15 18:19:53 UTC 2023
PRIMARY
Related Record Type Details
Structure of .GAMMA.-AMINO-.BETA.-HYDROXYBUTYRIC ACID, (-)-
RACEMATE -> ENANTIOMER
Structure of .GAMMA.-AMINO-.BETA.-HYDROXYBUTYRIC ACID, (+)-
RACEMATE -> ENANTIOMER
Related Record Type Details
Structure of .GAMMA.-AMINO-.BETA.-HYDROXYBUTYRIC ACID
ACTIVE MOIETY
NIH
NCATS
PRIVACY ACT
ACCESSIBILITY
DISCLAIMER
HHS VULNERABILITY DISCLOSURE
For language access assistance, contact the NCATS Public Information Officer
National Center for Advancing Translational Sciences (NCATS),
6701 Democracy Boulevard, Bethesda MD 20892-4874 • 301-594-8966