A2129

Sigma-Aldrich

γ-Aminobutyric acid

≥99%

Synonym(s):
3-Carboxypropylamine, GABA, Piperidinic acid, 4-Aminobutanoic acid, gamma-Aminobutyric acid, Piperidic acid
Linear Formula:
NH2(CH2)3COOH
CAS Number:
Molecular Weight:
103.12
Beilstein/REAXYS Number:
906818
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.32

Quality Level

assay

≥99%

mp

195 °C (dec.) (lit.)

SMILES string

NCCCC(O)=O

InChI

1S/C4H9NO2/c5-3-1-2-4(6)7/h1-3,5H2,(H,6,7)

InChI key

BTCSSZJGUNDROE-UHFFFAOYSA-N

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Application

γ-Aminobutyric acid (GABA) has been used:
  • in the preparation of GABA–BSA (bovine serum albumin)–GA (glutaraldehyde) conjugate, which is used as a control for GABA immunostaining
  • in the macromolecule suppressed detection of GABA by magnetic resonance spectroscopy (MRS)
  • in the intraintestinal application of GABA in order to increase intraluminal fluid secretion

Biochem/physiol Actions

GABA (γ-Aminobutyric acid) is an amino acid that functions as an inhibitory neurotransmitter in the central nervous system and also functions as a neuromodulator in some peripheral tissues. It binds to GABAA receptor and inhibits the activity of signal-receiving neurons. The GABAA receptors are found to form a channel in the cell membranes of neurons. Upon binding of GABA, the receptor is activated to allow the passage of negatively charged molecules, such as chloride ions, into the cell. This results in lowering of excitability of the cell.
GABAergic neurons are involved in myorelaxation, anxiolytic treatment, sedation, and anaesthetics. GABA can also influence heart rate and blood pressure.
Major inhibitory neurotransmitter in brain; GABAA and GABAB receptor agonist; increases Cl conductance.

Features and Benefits

This compound is also offered as part of Sigma′s Library of Pharmacologically Active Compounds (LOPAC®1280), a biologically annotated collection of high-quality, ready-to-screen compounds. Click here to learn more.

Legal Information

LOPAC is a registered trademark of Sigma-Aldrich Co. LLC

storage_class_code

11 - Combustible Solids

WGK Germany

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

Certificate of Analysis

Certificate of Origin

S J Mihic et al.
Alcohol health and research world, 21(2), 127-131 (1997-01-01)
The neurotransmitter gamma-aminobutyric acid (GABA) inhibits the activity of signal-receiving neurons by interacting with the GABAA receptor on these cells. The GABAA receptor is a channel-forming protein that allows the passage of chloride ions into the cells. Excessive GABAA activation...
R Fabian-Fine et al.
The Journal of neuroscience : the official journal of the Society for Neuroscience, 19(1), 298-310 (1998-12-31)
The mechanosensory organs of arachnids receive diverse peripheral inputs. Little is known about the origin, distribution, and function of these chemical synapses, which we examined in lyriform slit sense organ VS-3 of the spider Cupiennius salei. The cuticular slits of...
Isabelle Niespodziany et al.
Epilepsia, 61(5), 914-923 (2020-04-17)
The antiepileptic drug candidate, padsevonil, is the first in a novel class of drugs designed to interact with both presynaptic and postsynaptic therapeutic targets: synaptic vesicle 2 proteins and γ-aminobutyric acid type A receptors (GABAA Rs), respectively. Functional aspects of...
Bo Hjorth Bentzen et al.
Advances in pharmacological sciences, 2011, 578273-578273 (2011-12-14)
Intuitively one might expect that activation of GABAergic inhibitory neurons results in bradycardia. In conscious animals the opposite effect is however observed. GABAergic neurons in nucleus ambiguus hold the ability to control the activity of the parasympathetic vagus nerve that...
Richard A E Edden et al.
Magnetic resonance in medicine, 68(3), 657-661 (2012-07-11)
Edited magnetic resonance spectroscopy makes possible noninvasive studies of the role of the inhibitory neurotransmitter GABA in the healthy brain and in disease processes. A major limitation of the methodology is coediting of macromolecular signals. Although it has previously been...
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