Thio-THIP

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Thio-THIP
Clinical data
Other names4,5,6,7-Tetrahydroisothiazolo[5,4-c]pyridin-3-ol; Thiogaboxadol
Drug classGABAA receptor weak partial agonist or antagonist; GABAA-ρ receptor antagonist; GABA reuptake inhibitor
ATC code
  • None
Identifiers
  • 4,5,6,7-tetrahydro-[1,2]thiazolo[5,4-c]pyridin-3-one
CAS Number
PubChem CID
ChemSpider
KEGG
ChEBI
ChEMBL
Chemical and physical data
FormulaC6H8N2OS
Molar mass156.20 g·mol−1
3D model (JSmol)
  • C1CNCC2=C1C(=O)NS2
  • InChI=1S/C6H8N2OS/c9-6-4-1-2-7-3-5(4)10-8-6/h7H,1-3H2,(H,8,9)
  • Key:DZYJTJJQGHXSFN-UHFFFAOYSA-N

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

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References

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  1. ^ a b Krogsgaard-Larsen P, Frølund B, Liljefors T (2002). "Specific GABA(A) agonists and partial agonists". Chemical Record. 2 (6): 419–430. doi:10.1002/tcr.10040. PMID 12469353.
  2. ^ a b Krogsgaard-Larsen P, Frølund B, Liljefors T (2006). "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. Vol. 54. pp. 53–71. doi:10.1016/s1054-3589(06)54003-7. ISBN 978-0-12-032957-1. PMID 17175810.
  3. ^ Brehm L, Ebert B, Kristiansen U, Wafford K, Kemp J, Krogsgaard-Larsen P (1997). "Structure and pharmacology of 4,5,6,7-tetrahydroisothiazolo[5,4-c]pyridin-3-ol (Thio-THIP), an agonist/antagonist at GABAA receptors". European Journal of Medicinal Chemistry. 32 (4): 357–363. doi:10.1016/S0223-5234(97)89089-7. Retrieved 5 October 2025.
  4. ^ 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.
  5. ^ 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.
  6. ^ a b Krogsgaard-Larsen P, Brehm L, Schaumburg K (1981). "Muscimol, a psychoactive constituent of Amanita muscaria, as a medicinal chemical model structure". Acta Chemica Scandinavica. Series B. 35 (5): 311–324. doi:10.3891/acta.chem.scand.35b-0311. PMID 6274117.
  7. ^ a b Krogsgaard-Larsen P, Mikkelsen H, Jacobsen P, Falch E, Curtis DR, Peet MJ, et al. (June 1983). "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. doi:10.1021/jm00360a020. PMID 6304315.
  8. ^ a b c Krogsgaard-Larsen P, Frølund B, Jørgensen FS, Schousboe A (August 1994). "GABAA receptor agonists, partial agonists, and antagonists. Design and therapeutic prospects". Journal of Medicinal Chemistry. 37 (16): 2489–2505. doi:10.1021/jm00042a001. PMID 8057295.
  9. ^ Krogsgaard-Larsen P (December 1981). "gamma-Aminobutyric acid agonists, antagonists, and uptake inhibitors. Design and therapeutic aspects". Journal of Medicinal Chemistry. 24 (12): 1377–1383. doi:10.1021/jm00144a001. PMID 6118436.
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