Gamma-Aminobutyric Acid
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Basic information
- CAS
56-12-2- Standard SMILES
NCCCC(=O)O- InChIKey
BTCSSZJGUNDROE-UHFFFAOYSA-N- Molecular formula
- C4H9NO2
- Average molar mass
- 103.12 g/mol
- Monoisotopic mass
- 103.06332853
Overview
Gamma-aminobutyric acid is a gamma-amino acid that is butanoic acid with the amino substituent located at C-4. It has a role as a neurotransmitter, a signalling molecule, a Saccharomyces cerevisiae metabolite and a human metabolite. It is a monocarboxylic acid and a gamma-amino acid. It is functionally related to a butyric acid. It is a conjugate acid of a gamma-aminobutyrate. It is a tautomer of a gamma-aminobutyric acid zwitterion.
Names & identifiers
- Preferred name
- Gamma-Aminobutyric Acid
- IUPAC
- 4-aminobutanoic acid
- English name
- 4-Aminobutyric acid
- Molecular formula
- C4H9NO2
- Molecular weight
- 103.12
Names & synonyms
gamma-aminobutyric acidGABA56-12-2Piperidic acidPiperidinic acidAminalonGaballonMielomadeGamarexGammalonGammarGammasol
Show more names
4-AMINOBUTANOIC ACIDgammaγ-Aminobutyric acidY-Aminobutyric acid56-12-6H-GABA-OHaminobutyric
butanoic acid, 4-amino-GammaloneButyric acid, 4-amino-gamma-Aminobutanoic acidImmu-Ggamma-amino-n-butyric acidGammageeGamulin
Database identifiers
- CAS
56-12-2- PubChem CID
- 119
- DTXSID
DTXSID6035106- ChEMBL
CHEMBL96- ChEBI
CHEBI:16865- UNII
- 2ACZ6IPC6I
- Nikkaji
- J1.375G
Properties
Computed structural propertiesFilling in
- XLogP
- -3.2
- Topological polar surface area
- 63.3 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 3
- Rotatable bonds
- 3
- Heavy atoms
- 7
- Formal charge
- 0
- Complexity
- 62.7
Experimental & physicochemical properties
DrugsPharmaceuticals -> Listed in ZINC15
LipidsFatty Acyls [FA] -> Fatty Acids and Conjugates [FA01] -> Amino fatty acids [FA0110]
CosmeticsHair conditioning
LogP-3.17
Flavoring AgentsEU Flavoring substances
Solubility
1300.0 mg/mL
1.2 [ug/mL] (The mean of the results at pH 7.4)
Melting Point203 °C
Physical DescriptionSolid
Ionization Efficiency
Negative
-1.52
10.5
Agilent XCT
Electrospray ionization
ammonia (10nM)
Dissociation Constants10.6
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Hazard information
Regulatory Information
Chemical: Butanoic acid, 4-amino-
Commission Regulation (EC) No 1565/2000 (Repealed by Com. Implementing Reg. (EU) No 872/2012)
gamma-Aminobutyric acid: Does not have an individual approval but may be used under an appropriate group standard
Other Safety InformationEvaluation - Chemicals that are unlikely to require further regulation to manage risks to environment
Toxicology
Health Effects
Chronically high levels of GABA are associated with at least 5 inborn errors of metabolism including: D-2-Hydroxyglutaric Aciduria, 4-Hydroxybutyric Aciduria/Succinic Semialdehyde Dehydrogenase Deficiency, GABA-Transaminase Deficiency, Homocarnosinosis and Succinic semialdehyde dehydrogenase deficiency.
Carcinogen ClassificationNo indication of carcinogenicity to humans (not listed by IARC).
Safety data
- PPE
- dust mask type N95 (US), Eyeshields, Gloves
- wgk
- 2
- tsca
- TSCA listed
- rtecs
- ES6300000
- hs_code
- 29224995
- risk_code
- 36/37/38-20/21/22
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- hazard_code
- Xi,Xn
- hazard_note
- Irritant
- safety_code
Chemistry & industry
Pharmacology
ATC Code
N - Nervous system
QN - Nervous system
MeSH Pharmacological ClassificationSubstances used for their pharmacological actions on GABAergic systems. GABAergic agents include agonists, antagonists, degradation or uptake inhibitors, depleters, precursors, and modulators of receptor function.
Tissue LocationsAdrenal Cortex
Cellular LocationsExtracellular
Metabolite Pathways2-Hydroxyglutric Aciduria (D And L Form)
Uses & manufacturing
UsesThis is an endogenously produced metabolite found in the human body. It is used in metabolic reactions, catabolic reactions or waste generation.
Use ClassificationCosmetics -> Hair conditioning
General Manufacturing InformationButanoic acid, 4-amino-: ACTIVE
Applications
Description4-Aminobutyric acid (GABA) is the chief inhibitory neurotransmitter in the mammalian central nervous system. It plays a role in regulating neuronal excitability throughout the nervous system. In humans, GABA is also directly responsible for the regulation of muscle tone. Although chemically it is an amino acid, GABA is rarely referred to as such in the scientific or medical communities, because the term "amino acid," used without a qualifier, conventionally refers to the alpha amino acids, which GABA is not, nor is it ever incorporated into a protein. In spastic diplegia in humans, GABA absorption becomes impaired by nerves damaged from the condition's upper motor neuron lesion, which leads to hypertonia of the muscles signaled by those nerves that can no longer absorb GABA.
Related reactions
175 records
Compound notes
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