A3539
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:
Molecular Weight:
175.61
EC Number:
261-802-6
UNSPSC Code:
12352200
PubChem Substance ID:
Beilstein/REAXYS Number:
4552667
MDL number:
InChI key
OBZFLUDUSNCZKL-UHFFFAOYSA-N
InChI
1S/C7H9NO2.ClH/c8-6-3-1-2-5(4-6)7(9)10;/h1-3,6H,4,8H2,(H,9,10);1H
SMILES string
Cl[H].NC1CC(=CC=C1)C(O)=O
assay
≥98%
mp
203 °C (dec.) (lit.)
storage temp.
2-8°C
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
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
Eyeshields, Gloves, type N95 (US)
Regulatory Information
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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
C G Kim et al.
The Journal of biological chemistry, 273(11), 6030-6040 (1998-04-16)
The biosynthesis of ansamycin antibiotics, like rifamycin B, involves formation of 3-amino-5-hydroxybenzoic acid (AHBA) by a novel variant of the shikimate pathway. AHBA then serves as the starter unit for the assembly of a polyketide which eventually links back to
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
Viktor Demko et al.
Journal of plant physiology, 167(9), 693-700 (2010-02-05)
Synthesis of 5-aminolevulinic acid (ALA) represents a rate limiting step in the tetrapyrrole biosynthetic pathway, and is regulated by metabolic feedback control of glutamyl-tRNA reductase (GluTR) activity. The FLU protein has been attributed to this regulation. Later in the biosynthetic
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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