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
Beilstein:
4552667
EC Number:
MDL number:
UNSPSC Code:
12352200
PubChem Substance ID:
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
Regulatory Information
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A S Taisova et al.
Mikrobiologiia, 75(2), 165-171 (2006-06-09)
We determined the concentrations of bacteriochlorophylls (BChl) in the light-harvesting antennae of Oscillochloris trichoides (of the family Oscillochloridaceae belonging to green filamentous mesophilic bacteria) cultivated either with gabaculine, an inhibitor of the C-5 pathway of BChl biosynthesis in a number
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
Tatsuru Masuda et al.
Plant physiology, 128(2), 603-614 (2002-02-14)
To elucidate the mechanism of an irradiance-dependent adjustment in the chlorophyll (Chl) antenna size of Dunaliella salina, we investigated the regulation of expression of the Chl a oxygenase (CAO) and light-harvesting complex b (Lhcb) genes as a function of Chl
J C Eads et al.
Biochemistry, 38(31), 9840-9849 (1999-08-06)
The biosynthesis of ansamycin antibiotics, including rifamycin B, involves the synthesis of an aromatic precursor, 3-amino-5-hydroxybenzoic acid (AHBA), which serves as starter for the assembly of the antibiotics' polyketide backbone. The terminal enzyme of AHBA formation, AHBA synthase, is a
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
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