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:
Pricing and availability is not currently available.
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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.[1] 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.[1]
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.[1]
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
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Daniele Rosellini et al.
Plant cell reports, 26(7), 1035-1044 (2007-03-03)
A selectable marker gene (SMG), usually conferring resistance to an antibiotic or herbicide, is generally introduced into the plant cells with the gene(s) for the trait of interest to allow only the cells that have integrated and express the foreign
Moonhee Lee et al.
Glia, 59(11), 1600-1611 (2011-07-13)
We have previously demonstrated that human astrocytes are GABAergic cells. Throughout the adult human brain, they express the GABA synthesizing enzyme GAD 67, the GABA metabolizing enzyme GABA-T, and the GABA(A) and GABA(B) receptors. GABA modulates the actions of microglia
George L Orriss et al.
FASEB journal : official publication of the Federation of American Societies for Experimental Biology, 24(2), 404-414 (2009-09-30)
Gabaculine is a potent inhibitor of the vitamin B6-dependent key enzyme in chlorophyll biosynthesis, glutamate-1-semialdehyde aminomutase (GSAM). The inhibition effect is caused by an enzymatic deprotonation of the neurotoxin and requires the aldimine (PLP) form of the cofactor at the
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'
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
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