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T101

Sigma-Aldrich

Gaboxadol hydrochloride

solid, ≥98% (HPLC)

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Synonym(s):
4,5,6,7-Tetrahydroisoxazolo[5,4-c]pyridin-3-ol hydrochloride, THIP hydrochloride
Empirical Formula (Hill Notation):
C6H8N2O2 · HCl
CAS Number:
85118-33-8
Molecular Weight:
176.60
EC Number:
285-687-7
MDL number:
MFCD00055180
PubChem Substance ID:
57654649
NACRES:
NA.22

Quality Level

100

Assay

≥98% (HPLC)

form

solid

storage condition

desiccated

color

white

solubility

ethanol: 0.91 mg/mL
H2O: 20 mg/mL

SMILES string

Cl[H].Oc1noc2CNCCc12

InChI

1S/C6H8N2O2.ClH/c9-6-4-1-2-7-3-5(4)10-8-6;/h7H,1-3H2,(H,8,9);1H

InChI key

ZDZDSZQYRBZPNN-UHFFFAOYSA-N

Gene Information

human ... GABRA1(2554) , GABRA2(2555) , GABRA3(2556) , GABRA4(2557) , GABRA5(2558) , GABRA6(2559) , GABRB1(2560) , GABRB2(2561) , GABRB3(2562)

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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.

Caution

Photosensitive

Storage Class Code

11 - 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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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)
GABA Site Agonist Gaboxadol Induces Addiction-Predicting Persistent Changes in Ventral Tegmental Area Dopamine Neurons But Is Not Rewarding in Mice or Baboons
Vashchinkina E, et al.
The Journal of Neuroscience, 32(15), 5310-5320 (2012)
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)
TEXTBOOK OF GERIATRIC MEDICINE INTERNATIONAL (2011)
Vanessa M Hill et al.
PLoS biology, 16(7), e2005206-e2005206 (2018-07-13)
Although sleep appears to be broadly conserved in animals, the physiological functions of sleep remain unclear. In this study, we sought to identify a physiological defect common to a diverse group of short-sleeping Drosophila mutants, which might provide insight into
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