GYKI-52,466

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GYKI-52,466[1][2][3][4][5][6][7]
GYKI 52466.svg
Names
IUPAC name
4-(8-methyl-9H-[1,3]dioxolo[4,5-h][2,3]benzodiazepin-5-yl)aniline
Identifiers
102771-26-6 YesY
192065-56-8 (HCl salt) N
ChEMBL ChEMBL275006 N
4210
Jmol 3D model Interactive image
PubChem 3538
  • CC1=NN=C(C2=CC3=C(C=C2C1)OCO3)C4=CC=C(C=C4)N
Properties
C17H15N3O2
Molar mass 293.32 g/mol
Appearance Yellow solid (HCl salt)
Density 1.393 g/cm3
>10 mg/mL (HCl salt)
Vapor pressure {{{value}}}
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YesYN ?)
Infobox references

GYKI-52466 is a 2,3-benzodiazepine that acts as an ionotropic glutamate receptor antagonist, which is a non-competitive AMPA receptor antagonist (IC50 values are 10-20, ~ 450 and >> 50 μM for AMPA- , kainate- and NMDA-induced responses respectively), orally-active anticonvulsant, and skeletal muscle relaxant. Unlike conventional 1,4-benzodiazepines, GYKI-52466 and related 2,3-benzodiazepines do not act on GABAA receptors. Like other AMPA receptor antagonists, GYKI-52466 has anticonvulsant and neuroprotective properties.

References

  1. ↑ Donevan, S.D., Rogawski, M.A., Allosteric regulation of alpha-amino-3-hydroxy-5-methyl-4-isoxazole-propionate receptors by thiocyanate and cyclothiazide at a common modulatory site distinct from that of 2,3-benzodiazepines. Neuroscience 87, 615, (1998)
  2. ↑ Donevan, S.D., Rogawski, M.A., GYKI 52466, a 2,3-benzodiazepine is a highly selective, non-competitive antagonist of AMPA/kainate receptor responses. Neuron 10, 51, (1993)
  3. ↑ Wilding, T.J., Huettner, J.E., Differential antagonism of alpha-amino-3-hydroxy-5-methyl-4- isoxazolepropionic acid-preferring and kainate-preferring receptors by 2,3-benzodiazepines. Mol. Pharmacol. 47, 582, (1995)
  4. ↑ Tarnawa et al. (1989) Electrophysiological studies with a 2,3-benzodiazepine muscle relaxant: GYKI 52466. Eur. J.Pharmacol. 167 193
  5. ↑ Paternain et al. (1995) Selective antagonism of AMPA receptors unmasks kainate receptor-mediated responses in hippocampal neurons. Neuron 14 185.
  6. ↑ Rzeski et al. (2001) Glutamate antagonists limit tumor growth. Proc. Natl.Acad. Sci.USA 98 6372.
  7. ↑ Szabados et al. (2001) Comparison of anticonvulsive and acute neuroprotective activity of three 2,3-benzodiazepine compounds, GYKI 52466, GYKI 53405, and GYKI 53655. Brain Res. Bull. 55 387.


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