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Thio-THIP

From Wikipedia, the free encyclopedia

Pharmaceutical compound
Thio-THIP
Clinical data
Other names4,5,6,7-Tetrahydroisothiazolo[5,4-c]pyridin-3-ol; Thiogaboxadol
Drug classGABAA receptor weakpartial agonist orantagonist;GABAA-ρ receptorantagonist;GABA reuptake inhibitor
ATC code
  • None
Identifiers
  • 4,5,6,7-tetrahydro-[1,2]thiazolo[5,4-c]pyridin-3-one
CAS Number
PubChemCID
ChemSpider
KEGG
ChEBI
ChEMBL
CompTox Dashboard(EPA)
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 as4,5,6,7-tetrahydroisothiazolo[5,4-c]pyridin-3-ol, is a low-potencyGABAA receptor very weakpartial agonist orantagonist related togaboxadol (THIP).[1][2][3] It is also a weakGABAA-ρ receptor antagonist[4][5] and a weakGABA 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 ofmuscimol andthiomuscimol, which are almostequipotent.[8] Like gaboxadol, thio-THIP is azwitterion.[1][8] It may cross theblood–brain barrier similarly to gaboxadol.[8] Thio-THIP was developed and described byPovl Krogsgaard-Larsen and colleagues by 1981.[6][9][7]

See also

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References

[edit]
  1. ^abKrogsgaard-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. ^abKrogsgaard-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. Retrieved5 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. ^abKrogsgaard-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. ^abKrogsgaard-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. ^abcKrogsgaard-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.
Ionotropic
GABAATooltip γ-Aminobutyric acid A receptor
GABAA-ρTooltip γ-Aminobutyric acid A-rho receptor
Metabotropic
GABABTooltip γ-Aminobutyric acid B receptor
GABATooltip γ-Aminobutyric acidmetabolism andtransportmodulators
Transporter
GATTooltip GABA transporter
VIAATTooltip Vesicular inhibitory amino acid transporter
Enzyme
GADTooltip Glutamate decarboxylase
GABA-TTooltip γ-Aminobutyrate aminotransferase
Other
Antivitamin B6
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