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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:
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 Code

13 - Non Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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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
P J Loida et al.
Archives of biochemistry and biophysics, 372(2), 230-237 (1999-12-22)
The metabolite 5-aminolevulinic acid (ALA) is an early committed intermediate in the biosynthetic pathway of heme and chlorophyll formation. In plants, 5-aminolevulinic acid is synthesized via a two-step pathway in which glutamyl-tRNA(Glu) is reduced by glutamyl-tRNA(Glu) reductase (GluTR) to glutamate
A B Patel et al.
Brain research, 919(2), 207-220 (2001-11-10)
The objective of the present study was to assess the degree to which astrocytic glutamine provides carbon for net synthesis of GABA in the rat neocortex in vivo. Isotopic labeling of GABA and glutamate from astrocytic glutamine was followed in
Christopher Sayer et al.
Acta crystallographica. Section D, Biological crystallography, 68(Pt 7), 763-772 (2012-07-04)
The three-dimensional structure of the Sulfolobus solfataricus serine:pyruvate aminotransferase has been determined to 1.8 Å resolution. The structure of the protein is a homodimer that adopts the type I fold of pyridoxal 5'-phosphate (PLP)-dependent aminotransferases. The structure revealed the PLP cofactor
M Fu et al.
Bioorganic & medicinal chemistry, 7(8), 1581-1590 (1999-09-11)
Gabaculine (5-amino-1,3-cyclohexadienylcarboxylic acid, 1), a naturally occurring neurotoxin isolated from Streptomyces toyocaenis, has been shown to be a mechanism-based inactivator of gamma-aminobutyric acid aminotransferase (GABA-AT) (Rando, R. R. Biochemistry 1977, 16, 4604). Inactivation results from reaction of gabaculine with the
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