Gamma-Aminobutyric Acid

HCID 119CAS 56-12-2

Basic information

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 properties

XLogP
-3.2
Topological polar surface area
63.3 Ų
Hydrogen bond donors
2
Hydrogen bond acceptors
3
Rotatable bonds
3
Heavy atoms
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 · 2 items

1300.0 mg/mL

1.2 [ug/mL] (The mean of the results at pH 7.4)

Physicochemical properties

Melting point
195 °C · 195 °C (dec.) (lit.)
Boiling point
248 · 248.0±23.0 °C(Predicted)
Density
1.23 · 1.2300 (estimate)
refractive index
1.465 · 1.4650 (estimate)
FEMA
4288 · 4288 | 4-AMINOBUTYRIC ACID
FLAVIS Number
17.035 · 17.035 | 4-Amino-butyric acid

Safety & regulation

Hazard information

Regulatory Information · 3 items

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Commission Regulation (EC) No 1565/2000 (Repealed by Com.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 · 1 item

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

Chemistry & industry

Pharmacology

ATC Code · 2 items

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 · 4 items

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.

History4-Aminobutyric acid was first synthesized in 1883, and was first known only as a plant and microbe metabolic product. In 1950, however, GABA was discovered to be an integral part of the mammalian central nervous system.

Uses4-Aminobutyric acid is an important inhibitory neurotransmitter in the central nervous system, which has good water solubility and thermal stability. It has been confirmed that GABA, as a small molecular weight non protein amino acid, has edible safety and can be used in the production of beverages and other foods. Studies have shown that a certain amount of GABA can improve the body's sleep quality and reduce blood pressure.The foods contain γ-aminobutyric acid (GABA) at an amount that shows immediate effect of suppressing autonomic nerve activity related to blood pressure increase. Reacts with isothiocyanates to produce thioureas which have antifungal activity.

General Description4-Aminobutyric acid is a chief inhibitory neurotransmitter, which is found in the cerebellum, hypothalamus, thalamus and hippocampus. It is formed via the decarboxylation of L-glutamate catalyzed by the enzyme, glutamic acid decarboxylase(GAD).

Preparation methods · 1 item

PreparationThe synthesis of 4-aminobutyric acid mainly includes the following: the first is the use of potassium Phthaloyl imine and γ- Chloroprene cyanogen or butyrolactone is used as the raw material of GABA. The final product obtained after violent reaction and hydrolysis is GABA; The second is to use pyrrolidone as the initial raw material, hydrolyze it through calcium hydroxide and ammonium bicarbonate, and finally open its ring to obtain GABA; The third is to use butyric acid and ammonia as raw materials of GABA γ GABA was obtained by light reaction under X-ray conditions; The fourth method is to synthesize GABA with propylamine and formic acid by glow discharge; The fifth is to use methyl bromoacetate and ethylene as raw materials to prepare GABA. Methyl 4-bromobutyrate is obtained through polymerization. Finally, the product after ammonolysis and hydrolysis is GABA. The chemical synthesis methods of GABA have the disadvantages of difficult reaction control and high cost.

Suppliers50 total

国药集团化学试剂有限公司86-21-63210123 · [email protected]
北京华美互利生物化工010-56205725 · [email protected]
梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
河北创之源生物科技有限公司13012111162
Additional notes · 1 item

Definition4-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 signalling molecule, a human metabolite, a Saccharomyces cerevisiae metabolite and a neurotransmitter. It is a gamma-amino acid and a monocarboxylic acid. It derives from a butyric acid. It is a conjugate acid of a gamma-aminobutyrate. It is a tautomer of a gamma-aminobutyric acid zwitterion.

Related reactions

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