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:
Product Name
Gaboxadol hydrochloride, solid, ≥98% (HPLC)
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
Related Categories
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
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.
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
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)
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 and Sleep: Molecular, Functional and Clinical Aspects (2010)
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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