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A3539

Sigma-Aldrich

3-Amino-2,3-dihydrobenzoic acid hydrochloride

≥98%

Synonym(s):

5-Amino-1,3-cyclohexadiene-1-carboxylic acid hydrochloride, Gabaculine hydrochloride

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About This Item

Empirical Formula (Hill Notation):
C7H9NO2 · HCl
CAS Number:
59556-17-1
Molecular Weight:
175.61
Beilstein/REAXYS Number:
4552667
EC Number:
261-802-6
MDL number:
MFCD00036983
UNSPSC Code:
12352200
PubChem Substance ID:
24278213

assay

≥98%

mp

203 °C (dec.) (lit.)

storage temp.

2-8°C

SMILES string

Cl[H].NC1CC(=CC=C1)C(O)=O

InChI

1S/C7H9NO2.ClH/c8-6-3-1-2-5(4-6)7(9)10;/h1-3,6H,4,8H2,(H,9,10);1H

InChI key

OBZFLUDUSNCZKL-UHFFFAOYSA-N

Gene Information

human ... GABRG1(2565) , GABRG2(2566) , GABRG3(2567)

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General description

γ-aminobutyric acid (GABA) is an inhibitory neurotransmitter that binds selective transmembrane receptors, resulting in gating of ion channels in the central nervous system. GABA that is released from the receptors is degraded by GABA-transaminase. Gabaculine (3-Amino-2,3-dihydrobenzoic acid) is a neurotoxin that was first isolated from Streptomyces toyocaenis and is a conformationally constrained analog of GABA. Gabaculine inhibits GABA-transaminase, which results in an increase of endogenous GABA in the brain and spinal cord.

Biochem/physiol Actions

3-Amino-2,3-dihydrobenzoic acid hydrochloride potently and specifically inhibits GABA-transaminase (GABA-T), resulting in inhibited degradation of GABA. May inhibit glutamic acid decarboxylase (GAD), though it is 1000-fold more effective as a GABA-T inhibitor than as a GAD inhibitor.

Storage Class

13 - Non Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

Certificates of Analysis (COA)

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D O'sullivan et al.
The Biochemical journal, 330 ( Pt 2), 627-632 (1998-04-18)
The metabolism of 14C-labelled arginine and ornithine was studied in the isolated, nonrecirculating, perfused rat liver. The catabolism of these amino acids required ornithine aminotransferase since treatment of rats with gabaculine, an inhibitor of this enzyme, decreased substantially the production
C Piérard et al.
Experimental brain research, 127(3), 321-327 (1999-08-19)
The aim of this work was to study the neurochemical effects in the brain of GABA-transaminase inhibition by systemic administration of gabaculine (100 mg/kg, i.a.) in the rat. In order to investigate neurotransmitter and related amino-acid compartmentation and metabolism, we
Inés Hernández-Fisac et al.
The Biochemical journal, 400(1), 81-89 (2006-07-06)
OMP (oxo-4-methylpentanoic acid) stimulates by itself a biphasic secretion of insulin whereas L-leucine requires the presence of L-glutamine. L-Glutamine is predominantly converted into GABA (gamma-aminobutyric acid) in rat islets and L-leucine seems to promote its metabolism in the 'GABA shunt'
Jehoon Yang et al.
Journal of neuroscience methods, 182(2), 236-243 (2009-06-23)
Previous in vivo magnetic resonance spectroscopy (MRS) studies of gamma-aminobutyric acid (GABA) synthesis have relied on (13)C label incorporation into GABA C2 from [1-(13)C] or [1,6-(13)C(2)]glucose. In this study, the [(13)C]GABA C1 signal at 182.3 ppm in the carboxylic/amide spectral
Masahiro Irifune et al.
Canadian journal of anaesthesia = Journal canadien d'anesthesie, 54(12), 998-1005 (2007-12-07)
gamma-Aminobutyric acid (GABA) and N-methyl-D-aspartate (NMDA) receptors are important targets for anesthetic action at the in vitro cellular level. Gabaculine is a GABA-trans-aminase inhibitor that increases endogenous GABA in the brain, and enhances GABA activity. We have recently shown that
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