Chemistry:Thio-THIP

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Thio-THIP, also known as 4,5,6,7-tetrahydroisothiazolo[5,4-c]pyridin-3-ol, is a low-potency GABAA receptor very weak partial agonist or antagonist related to gaboxadol (THIP).[1][2][3] It is also a weak GABAA-ρ receptor antagonist[4][5] and a weak GABA reuptake inhibitor.[2] The drug has three orders of magnitude lower potency as a GABAA receptor modulator than gaboxadol.[6][7] This is unlike the case of muscimol and thiomuscimol, which are almost equipotent.[8] Like gaboxadol, thio-THIP is a zwitterion.[1][8] It may cross the blood–brain barrier similarly to gaboxadol.[8] Thio-THIP was developed and described by Povl Krogsgaard-Larsen and colleagues by 1981.[6][9][7]

See also

References

  1. ↑ 1.0 1.1 "Specific GABA(A) agonists and partial agonists". Chemical Record 2 (6): 419–430. 2002. doi:10.1002/tcr.10040. PMID 12469353. 
  2. ↑ 2.0 2.1 "GABAA Agonists and Partial Agonists: THIP (Gaboxadol) as a Non-Opioid Analgesic and a Novel Type of Hypnotic1". GABA(A) agonists and partial agonists: THIP (Gaboxadol) as a non-opioid analgesic and a novel type of hypnotic. Advances in Pharmacology. 54. 2006. pp. 53–71. doi:10.1016/s1054-3589(06)54003-7. ISBN 978-0-12-032957-1. 
  3. ↑ "Structure and pharmacology of 4,5,6,7-tetrahydroisothiazolo[5,4-cpyridin-3-ol (Thio-THIP), an agonist/antagonist at GABAA receptors"]. European Journal of Medicinal Chemistry 32 (4): 357–363. 1997. doi:10.1016/S0223-5234(97)89089-7. https://linkinghub.elsevier.com/retrieve/pii/S0223523497890897. Retrieved 5 October 2025. 
  4. ↑ "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. 
  5. ↑ "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. 
  6. ↑ 6.0 6.1 "Muscimol, a psychoactive constituent of Amanita muscaria, as a medicinal chemical model structure". Acta Chemica Scandinavica. Series B 35 (5): 311–324. 1981. doi:10.3891/acta.chem.scand.35b-0311. PMID 6274117. 
  7. ↑ 7.0 7.1 "4,5,6,7-Tetrahydroisothiazolo[5,4-c]pyridin-3-ol and related analogues of THIP. Synthesis and biological activity". Journal of Medicinal Chemistry 26 (6): 895–900. June 1983. doi:10.1021/jm00360a020. PMID 6304315. 
  8. ↑ 8.0 8.1 8.2 "GABAA receptor agonists, partial agonists, and antagonists. Design and therapeutic prospects". Journal of Medicinal Chemistry 37 (16): 2489–2505. August 1994. doi:10.1021/jm00042a001. PMID 8057295. 
  9. ↑ "gamma-Aminobutyric acid agonists, antagonists, and uptake inhibitors. Design and therapeutic aspects". Journal of Medicinal Chemistry 24 (12): 1377–1383. December 1981. doi:10.1021/jm00144a001. PMID 6118436. 

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See also
Receptor/signaling modulators
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