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A3539 Sigma-Aldrich

3-Amino-2,3-dihydrobenzoic acid hydrochloride

≥98%

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

  • CAS Number 59556-17-1

  • Empirical Formula (Hill Notation) C7H9NO2 · HCl

  • Molecular Weight 175.61

  •  Beilstein/REAXYS Number 4552667

  •  EC Number 261-802-6

  •  MDL number MFCD00036983

  •  PubChem Substance ID 24278213

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Properties

Related Categories Cell Biology, Cell Signaling and Neuroscience, Enzyme Inhibitors, GABA-Transaminase, Neuroscience,
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)

Description

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.

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

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Safety & Documentation

Safety Information

Personal Protective Equipment 
RIDADR 
NONH for all modes of transport
WGK Germany 
3
RTECS 
GU4775000

Documents

Certificate of Analysis (COA)

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Certificate of Origin (COO)

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Protocols & Articles
Peer-Reviewed Papers
15

References

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