THAZ

THAZ
Clinical data
Drug classGABAA-ρ receptor antagonist; GABAA receptor antagonist; Glycine receptor antagonist
ATC code
  • None
Identifiers
  • 5,6,7,8-tetrahydro-4H-[1,2]oxazolo[4,5-d]azepin-3-one
CAS Number
PubChem CID
ChemSpider
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC7H10N2O2
Molar mass154.169 g·mol−1
3D model (JSmol)
  • C1CNCCC2=C1C(=O)NO2
  • 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

THAZ, also known as 5,6,7,8-tetrahydro-4H-isoxazolo(4,5-d)azepin-3-ol, is a moderately potent GABAA-ρ receptor antagonist related to gaboxadol (THIP).[1][2] Unlike gaboxadol, it is said to be virtually inactive at the GABAA receptor.[1] However, in other studies, it showed significant affinity for the GABAA receptor, where it appeared to act as an antagonist.[2][3] In addition to its GABAA-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-HT2A and 5-HT2C receptor agonists.[5][6]

See also

References

  1. ^ a b Frølund B, Ebert B, Kristiansen U, Liljefors T, Krogsgaard-Larsen P (August 2002). "GABA(A) receptor ligands and their therapeutic potentials". Current Topics in Medicinal Chemistry. 2 (8): 817–832. doi:10.2174/1568026023393525. PMID 12171573. Like thio-THIP, the structurally related THIP analogues, aza-THIP, iso-THIP and THAZ (Fig. 4) are virtually inactive at the GABAA receptors [51, 52], but disclose antagonistic effects at the GABAC receptors [53].
  2. ^ a b c Krehan D, Frølund B, Ebert B, Nielsen B, Krogsgaard-Larsen P, Johnston GA, et al. (November 2003). "Aza-THIP and related analogues of THIP as GABA C antagonists". Bioorganic & Medicinal Chemistry. 11 (23): 4891–4896. doi:10.1016/j.bmc.2003.09.016. PMID 14604650.
  3. ^ a b c Arnt J, Krogsgaard-Larsen P (November 1979). "GABA agonists and potential antagonists related to muscimol". Brain Research. 177 (2): 395–400. doi:10.1016/0006-8993(79)90793-5. PMID 227538.
  4. ^ Krogsgaard-Larsen P, Hjeds H, Curtis DR, Leah JD, Peet MJ (November 1982). "Glycine antagonists structurally related to muscimol, THIP, or isoguvacine". Journal of Neurochemistry. 39 (5): 1319–1324. doi:10.1111/j.1471-4159.1982.tb12573.x. PMID 6288870.
  5. ^ Duan W, Cao D, Wang S, Cheng J (January 2024). "Serotonin 2A Receptor (5-HT2AR) Agonists: Psychedelics and Non-Hallucinogenic Analogues as Emerging Antidepressants". Chemical Reviews. 124 (1): 124–163. doi:10.1021/acs.chemrev.3c00375. PMID 38033123.
  6. ^ Jensen AA, Plath N, Pedersen MH, Isberg V, Krall J, Wellendorph P, et al. (February 2013). "Design, synthesis, and pharmacological characterization of N- and O-substituted 5,6,7,8-tetrahydro-4H-isoxazolo[4,5-d]azepin-3-ol analogues: novel 5-HT(2A)/5-HT(2C) receptor agonists with pro-cognitive properties". Journal of Medicinal Chemistry. 56 (3): 1211–1227. doi:10.1021/jm301656h. PMID 23301527.
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