Thiomuscimol

Thiomuscimol
Clinical data
Other names5-Aminomethyl-3-isothiazol
Drug classGABAA receptor agonist
ATC code
  • None
Identifiers
  • 5-(Aminomethyl)-1,2-thiazol-3-ol
CAS Number
PubChem CID
ChemSpider
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC4H6N2OS
Molar mass130.17 g·mol−1
3D model (JSmol)
Melting point140 °C (284 °F) (decomp.)[1]
  • C1=C(SN=C1O)CN
  • InChI=1S/C4H6N2OS/c5-2-3-1-4(7)6-8-3/h1H,2,5H2,(H,6,7)
  • Key:QVBUOPGWPXUAHT-UHFFFAOYSA-N

Thiomuscimol, also known as 5-aminomethyl-3-isothiazol, is a synthetic GABAA receptor agonist which is structurally related to the naturally occurring GABAA receptor agonist muscimol (found in Amanita muscaria).[2][3] It is approximately equipotent with muscimol as a GABAA receptor agonist in vitro.[4] Unlike muscimol however, thiomuscimol does not to any extent additionally act as a GABA reuptake inhibitor.[2] On the other hand, like muscimol, it is a substrate for and metabolized by GABA transaminase (GABA-T), which is said to have limited its usefulness and application in animal behavioral studies.[2][5] The drug was first described in the scientific literature by Povl Krogsgaard-Larsen and colleagues by 1976.[1][6][3] It was encountered as a novel designer drug online in 2024.[7][8]

See also

References

  1. ^ a b Lykkeberg J, Krogsgaard-Larsen P, Garegg PJ, Norberg T, Pilotti AM, Anthonsen T (1976). "Structural Analogues of GABA. Synthesis of 5-Aminomethyl-3-isothiazolol (Thiomuscimol)" (PDF). Acta Chemica Scandinavica. 30b: 781–785. doi:10.3891/acta.chem.scand.30b-0781.
  2. ^ a b c Falch E, Larsson OM, Schousboe A, Krogsgaard-Larsen P (1990). "GABA‐A agonists and GABA uptake inhibitors: Structure‐activity relationships". Drug Development Research. 21 (3): 169–188. doi:10.1002/ddr.430210304. ISSN 0272-4391. Retrieved 4 October 2025.
  3. ^ a b Krogsgaard-Larsen P, Hjeds H, Curtis DR, Lodge D, Johnston GA (June 1979). "Dihydromuscimol, thiomuscimol and related heterocyclic compounds as GABA analogues". Journal of Neurochemistry. 32 (6): 1717–1724. doi:10.1111/j.1471-4159.1979.tb02284.x. PMID 448364.
  4. ^ Krogsgaard-Larsen P, Christensen A (1980). "Chapter 5. GABA Agonists and Antagonists". Annual Reports in Medicinal Chemistry. Vol. 15. Elsevier. pp. 41–50. doi:10.1016/s0065-7743(08)60366-8. ISBN 978-0-12-040515-2. Retrieved 4 October 2025.
  5. ^ Krogsgaard-Larsen P, Falch E (August 1981). "GABA agonists. Development and interactions with the GABA receptor complex". Molecular and Cellular Biochemistry. 38 Spec No (Pt 1): 129–146. doi:10.1007/BF00235692. PMID 6270544.
  6. ^ Krogsgaard-Larsen P, Hjeds H, Curtis DR, Lodge D, Johnston GA (1977). "Thiomuscimol, isomuscimol, and related compounds as GABA agonists". Proc. Int. Soc. Neurochem. 6: 626.
  7. ^ "Тиомусцимол (Thiomuscimol)". АИПСИН (in Russian). 15 March 1995. Retrieved 13 October 2025.
  8. ^ "Тиомусцимол (Thiomuscimol)". АИПСИН (in Russian). 15 March 1995. Retrieved 1 January 2026.
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