T101
Gaboxadol hydrochloride
solid, ≥98% (HPLC)
Synonym(s):
4,5,6,7-Tetrahydroisoxazolo[5,4-c]pyridin-3-ol hydrochloride, THIP hydrochloride
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About This Item
Empirical Formula (Hill Notation):
C6H8N2O2 · HCl
CAS Number:
Molecular Weight:
176.60
NACRES:
NA.22
PubChem Substance ID:
UNSPSC Code:
12352100
EC Number:
285-687-7
MDL number:
Assay:
≥98% (HPLC)
Form:
solid
InChI key
ZDZDSZQYRBZPNN-UHFFFAOYSA-N
InChI
1S/C6H8N2O2.ClH/c9-6-4-1-2-7-3-5(4)10-8-6;/h7H,1-3H2,(H,8,9);1H
SMILES string
Cl[H].Oc1noc2CNCCc12
assay
≥98% (HPLC)
form
solid
storage condition
desiccated
color
white
solubility
ethanol: 0.91 mg/mL, H2O: 20 mg/mL
Quality Level
Gene Information
General description
Gaboxadol, also referred to as 4,5,6,7-tetrahydroisoxazolo(5,4-c)pyridin-3-ol (THIP), is a GABA site agonist. It has great affinity to the δ subunit of extrasynaptic high-affinity GABAA receptors. Gaboxadol was first developed for the treatment of schizophrenia, epilepsy, primary insomnia and Huntington′s disease. It can easily cross the blood-brain barrier and is rapidly absorbed by the body.
Application
Gaboxadol hydrochloride has been used in cell migration and invasion assay to assess liver cancer cell migration.
Biochem/physiol Actions
GABAA receptor agonist.
Disclaimer
Photosensitive
Storage Class
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
Eyeshields, Gloves, type N95 (US)
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P Krogsgaard-Larsen et al.
Journal of medicinal chemistry, 26(6), 895-900 (1983-06-01)
The thio analogues of the GABA (gamma-aminobutyric acid) agonist THIP (4,5,6,7-tetrahydroisoxazolo[5,4-c]pyridin-3-ol), the GABA uptake inhibitor THPO (4,5,6,7-tetrahydroisoxazolo[4,5-c]pyridin-3-ol), and the glycine antagonist THAZ (5,6,7,8-tetrahydro-4H-isoxazolo[4,5-d]azepin-3-ol) have been synthesized and tested biologically on single neurons in the cat spinal cord and in vitro
Zhiwen Ye et al.
Frontiers in neural circuits, 7, 203-203 (2014-01-07)
We have made use of the δ subunit-selective allosteric modulator DS2 (4-chloro-N-[2-(2-thienyl)imidazo[1,2-a]pyridine-3-yl benzamide) to assay the contribution of δ-GABAARs to tonic and phasic conductance changes in the cerebellum, thalamus and neocortex. In cerebellar granule cells, an enhancement of the tonic
GABA(A) agonists and partial agonists: THIP (Gaboxadol) as a non-opioid analgesic and a novel type of hypnotic.
Krogsgaard-Larsen P, et al.
Biochemical Pharmacology, 68(8), 1573-1580 (2004)
Tissue transglutaminase and its role in human cancer progression.
Bo Li et al.
Advances in enzymology and related areas of molecular biology, 78, 247-293 (2012-01-10)
Suppression of Human Liver Cancer Cell Migration and Invasion via the GABAA Receptor
Chen ZA, et al.
Cancer Biology & Medicine, 9(2), 90-90 (2012)
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