A44401
γ-Aminobutyric acid
97%
Synonym(s):
3-Carboxypropylamine, 4-Aminobutanoic acid, GABA, Piperidic acid, Piperidinic acid
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About This Item
Linear Formula:
NH2(CH2)3COOH
CAS Number:
Molecular Weight:
103.12
EC Number:
200-258-6
UNSPSC Code:
12352103
MDL number:
Beilstein/REAXYS Number:
906818
InChI
1S/C4H9NO2/c5-3-1-2-4(6)7/h1-3,5H2,(H,6,7)
InChI key
BTCSSZJGUNDROE-UHFFFAOYSA-N
SMILES string
NCCCC(O)=O
assay
97%
mp
195 °C (dec.) (lit.)
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Application
Important inhibitory neurotransmitter. Reacts with isothiocyanates to produce thioureas which have antifungal activity.
Biochem/physiol Actions
Major inhibitory neurotransmitter in brain; GABAA and GABAB receptor agonist; increases Cl− conductance.
Storage Class
11 - Combustible Solids
wgk
WGK 1
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
dust mask type N95 (US), Eyeshields, Gloves
Regulatory Information
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Chem. Abstr., 120, 225805w-225805w (1994)
E Roberts et al.
Neurochemical research, 18(4), 365-376 (1993-04-01)
Alone of the known neurotransmitters, GABA is an electroneutral zwitterion (pI = 7.3) at physiological pH. This confers the highest probability of successfully traversing densely packed synaptic gaps without interacting electrostatically with charged entities enroute, making GABA a high fidelity
European Journal of Medicinal Chemistry, 26, 723-723 (1991)
Abraham Nudelman et al.
Journal of medicinal chemistry, 51(9), 2858-2862 (2008-03-28)
The perphenazine and fluphenazine GABA esters 3 and 4 evaluated in rat models for antipsychotic activity displayed a significant decrease of catalepsy associated with increased prolactin blood levels. Efficacy was evaluated in the d-amphetamine-induced hyperactivity model, where perphenazine abolished hyperactivity
Michaela Jansen et al.
Journal of medicinal chemistry, 51(15), 4430-4448 (2008-07-25)
Drugs used to treat various disorders target GABA A receptors. To develop alpha subunit selective compounds, we synthesized 5-(4-piperidyl)-3-isoxazolol (4-PIOL) derivatives. The 3-isoxazolol moiety was substituted by 1,3,5-oxadiazol-2-one, 1,3,5-oxadiazol-2-thione, and substituted 1,2,4-triazol-3-ol heterocycles with modifications to the basic piperidine substituent
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