Chemistry:THAZ

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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

  • Aza-THIP
  • Iso-THIP
  • Thio-THIP
  • THPO

References

  1. ↑ 1.0 1.1 "GABA(A) receptor ligands and their therapeutic potentials". Current Topics in Medicinal Chemistry 2 (8): 817–832. August 2002. 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. ↑ 2.0 2.1 2.2 "Aza-THIP and related analogues of THIP as GABA C antagonists". Bioorganic & Medicinal Chemistry 11 (23): 4891–4896. November 2003. doi:10.1016/j.bmc.2003.09.016. PMID 14604650. 
  3. ↑ 3.0 3.1 3.2 "GABA agonists and potential antagonists related to muscimol". Brain Research 177 (2): 395–400. November 1979. doi:10.1016/0006-8993(79)90793-5. PMID 227538. 
  4. ↑ "Glycine antagonists structurally related to muscimol, THIP, or isoguvacine". Journal of Neurochemistry 39 (5): 1319–1324. November 1982. doi:10.1111/j.1471-4159.1982.tb12573.x. PMID 6288870. 
  5. ↑ "Serotonin 2A Receptor (5-HT2AR) Agonists: Psychedelics and Non-Hallucinogenic Analogues as Emerging Antidepressants". Chemical Reviews 124 (1): 124–163. January 2024. doi:10.1021/acs.chemrev.3c00375. PMID 38033123. 
  6. ↑ "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. February 2013. doi:10.1021/jm301656h. PMID 23301527. 

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See also
Receptor/signaling modulators
GABAA receptor positive modulators
GABA metabolism/transport modulators

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