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T101

Sigma-Aldrich

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:
85118-33-8
Molecular Weight:
176.60
EC Number:
285-687-7
MDL number:
MFCD00055180
UNSPSC Code:
12352100
PubChem Substance ID:
57654649
NACRES:
NA.22

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)

Related Categories

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

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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)
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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