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T101

Sigma-Aldrich

Gaboxadol -hydrochlorid

solid, ≥98% (HPLC)

Synonym(e):

4,5,6,7-Tetrahydroisoxazolo[5,4-c]pyridin-3-ol hydrochloride, THIP hydrochloride

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About This Item

Empirische Formel (Hill-System):
C6H8N2O2 · HCl
CAS-Nummer:
85118-33-8
Molekulargewicht:
176.60
EG-Nummer:
285-687-7
MDL-Nummer:
MFCD00055180
UNSPSC-Code:
12352100
PubChem Substanz-ID:
57654649
NACRES:
NA.22

Assay

≥98% (HPLC)

Form

solid

Lagerbedingungen

desiccated

Farbe

white

Löslichkeit

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

InChIKey

ZDZDSZQYRBZPNN-UHFFFAOYSA-N

Angaben zum Gen

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

Verwandte Kategorien

Allgemeine Beschreibung

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.

Anwendung

Gaboxadol hydrochloride has been used in cell migration and invasion assay to assess liver cancer cell migration.

Biochem./physiol. Wirkung

GABAA receptor agonist.

Vorsicht

Photosensitive

Lagerklassenschlüssel

11 - Combustible Solids

WGK

WGK 3

Flammpunkt (°F)

Not applicable

Flammpunkt (°C)

Not applicable

Persönliche Schutzausrüstung

Eyeshields, Gloves, type N95 (US)

Analysenzertifikate (COA)

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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
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)
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
M Lancel
Sleep, 22(1), 33-42 (1999-02-16)
This paper reviews the sleep effects of systemically administered agonistic modulators of GABAA receptors, including barbiturates, benzodiazepines, zolpidem, zopiclone and neuroactive steroids, and the selective GABAA agonists muscimol and THIP. To assess the involvement of GABAA receptors in the physiologic
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)
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