THAZ

THAZ, also known as 5,6,7,8-tetrahydro-4H-isoxazolo(4,5-d)azepin-3-ol, is a moderately potent GABA_A-ρ receptor antagonist related to gaboxadol (THIP).^[1][2] Unlike gaboxadol, it is said to be virtually inactive at the GABA_A receptor.^[1] However, in other studies, it showed significant affinity for the GABA_A receptor, where it appeared to act as an antagonist.^[2][3] In addition to its GABA_A-ρ receptor antagonism, THAZ is a very weak glycine receptor antagonist.^[2][4] In contrast to muscimol and gaboxadol, THAZ injected directly into the brain produced convulsions.^[3] The drug was first described in the scientific literature by Povl Krogsgaard-Larsen and colleagues by 1979.^[3] Derivatives of THAZ such as N-Bn-THAZ and O-Bn-THAZ have been found to act as serotonin 5-HT_2A and 5-HT_2C receptor agonists.^[5][6]

Drug classGABA_A-ρ receptor antagonist; GABA_A receptor antagonist; Glycine receptor antagonist

ATC code

• None

CAS Number

• 53658-58-5

PubChem CID

• 171289

Quick facts Clinical data, Drug class ...

THAZ

Clinical data
Drug class	GABAA-ρ receptor antagonist; GABAA receptor antagonist; Glycine receptor antagonist
ATC code	None
Identifiers
IUPAC name 5,6,7,8-tetrahydro-4H-[1,2]oxazolo[4,5-d]azepin-3-one
CAS Number	53658-58-5
PubChem CID	171289
ChemSpider	149751
ChEMBL	ChEMBL309689
CompTox Dashboard (EPA)	DTXSID00201893
Chemical and physical data
Formula	C7H10N2O2
Molar mass	154.169 g·mol−1
3D model (JSmol)	Interactive image
SMILES C1CNCCC2=C1C(=O)NO2
InChI InChI=1S/C7H10N2O2/c10-7-5-1-3-8-4-2-6(5)11-9-7/h8H,1-4H2,(H,9,10) Key:KHTRGFVHYPWHIZ-UHFFFAOYSA-N

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