64603-91-4

Basic information

• Product Name: THIP HYDROCHLORIDE
• Synonyms: THIP HYDROCHLORIDE;4,5,6,7-tetrahydroisoxazolo(5,4-c)pyridin-3(2h)-onehydrate;4-c)pyridin-3(2h)-one,4,5,6,7-tetrahydro-isoxazolo(hydrate;gaboxadol;4,5,6,7-TETRAHYDROISOXAZOLO[5,4-C]PYRIDIN-3-OL;4,5,6,7-TETRAHYDROISOXAZOLO[5,4-C]PYRIDIN-3-OL HYDROCHLORIDE;gaboxadol hydrochloride;4,5,6,7-Tetrahydroisoxazolo[5,4-c]pyridin-3(2H)-one
• CAS NO: 64603-91-4
• Molecular Formula: C₆H₈N₂O₂
• Molecular Weight: 176.6
• EINECS: 264-963-0
• Product Categories: GABA/Glycine receptor
• Mol File: 64603-91-4.mol
• Article Data: 3

Chemical Properties

• Melting Point: 242-244° (dec)
• Boiling Point: 340.5 °C at 760 mmHg
• Flash Point: 159.7 °C
• Appearance: white/solid
• Density: 1.36 g/cm³
• Vapor Pressure: 0.00113mmHg at 25°C
• Storage Temp.: Store at RT
• Solubility: ethanol: 0.91 mg/mL
• PKA: pKa (water, 25°): 4.44 ±0.03; 8.48 ±0.04
• Stability: Stable for 2 years from date of purchase as supplied. Solutions in DMSO or distilled water may be stored at -20°C for up to 3 months.
• CAS DataBase Reference: THIP HYDROCHLORIDE(CAS DataBase Reference)
• NIST Chemistry Reference: THIP HYDROCHLORIDE(64603-91-4)
• EPA Substance Registry System: THIP HYDROCHLORIDE(64603-91-4)

Safety Data

• Safety Statements: 22-24/25
• WGK Germany: 3
• RTECS: NY3396800
• Hazardous Substances Data: 64603-91-4(Hazardous Substances Data)

Usage

Description

Gaboxadol HCl (64603-91-4) is a GABA-A receptor agonist. Hypnotic agent.

Uses

GABAa agonist, GABAc antagonist

Biological Activity

Systemically active GABA A receptor agonist and GABA C receptor antagonist. Displays antinociceptive, anticonvulsant and sedative effects. Hypnotic agent that enhances delta activity within non-REM sleep in rats.

References

1) Meera et al. (2011), Molecular basis for the high THIP/gaboxadol sensitivity of extrasynaptic GABA(A) receptors; J. Neurophysiol., 106 2057

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

Upstream product

• 65202-62-2 methyl 3-hydroxy-4,5,6,7-tetraydroisoxazolo<5,4-c>pyridine-6-carboxylate 
• 815574-58-4 4,5,6,7-tetrahydroisoxazolo[5,4-c]pyridin-3-ol monohydrate 

Downstream Products

• 914291-73-9 gaboxadol, N,N-dibenzylethylenediamine salt 

Relevant articles and documents

GABOXADOL FORMS, COMPOSITIONS THEREOF, AND RELATED METHODS

The invention provides novel gaboxadol forms. These forms include salts, hydrates, solvates, and polymorphs of gaboxadol. The invention also provides novel compositions comprising these novel soluble forms and a suitable carrier. The invention also provides related methods of treatment. Compositions and methods of the invention of the invention have a number of uses, including the treatment or prevention of sleep disorders.

Heterocyclic compounds

The compound Ia STR1 has been shown to possess GABA-related activity. The invention relates to Ia and derivatives thereof, covered by the formula STR2 in which R" is hydrogen, acetyl or a group of the general formula STR3 in which R5 is C1-8 alkyl; phenyl; phenyl substituted in the 4-position with halogen, lower alkoxy, or lower alkyl; or phenylalkyl in which the phenyl group may be substituted in the 4-position with halogen, lower alkoxy, or lower alkyl; and salts thereof. Novel intermediates for preparing I are STR4 in which Alk is a lower alkyl group and Z is hydrogen or an amino-protecting group; STR5 wherein Z is hydrogen or an amino-protecting group, T is a group convertible, by hydrolysis, into an oxy group, and Q is a leaving group which, on reaction with hydroxylamine, forms a hydroxamic acid group; STR6 wherein Z and T are as defined above; STR7 wherein Z is as defined above, and W is hydrogen or a group removable to yield the free hydroxy group, with the proviso that at least one of Z and W is different from hydrogen.