GYKI 52466
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| Preferred IUPAC name
4-(8-Methyl-2H,9H-[1,3]dioxolo[4,5-h][2,3]benzodiazepin-5-yl)aniline | |
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3D model (JSmol)
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| ChemSpider | |
| ECHA InfoCard | 100.162.378 |
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PubChem CID
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CompTox Dashboard (EPA)
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| Properties | |
| C17H15N3O2 | |
| Molar mass | 293.326 g·mol−1 |
| Appearance | Yellow solid (HCl salt) |
| Density | 1.393 g/cm3 |
| >10 mg/mL (HCl salt) | |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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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.[1][2][3][4] Unlike conventional 1,4-benzodiazepines, GYKI 52466 and related 2,3-benzodiazepines do not act on GABAA receptors.[5] Like other AMPA receptor antagonists, GYKI 52466 has anticonvulsant and neuroprotective properties.[6]
See also
[edit]- GYKI 52895, another 2,3-benzodiazepine with other than GABAergic function
- Tifluadom
- Lufuradom
References
[edit]- ^ Donevan, S.D; Rogawski, M.A (1998). "Allosteric regulation of α-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 (3): 615–629. doi:10.1016/s0306-4522(98)00109-2. PMID 9758228. S2CID 14817743.
- ^ Donevan, Sean D.; Rogawski, Michael A. (1993). "GYKI 52466, a 2,3-benzodiazepine, is a highly selective, noncompetitive antagonist of AMPA/Kainate receptor responses". Neuron. 10 (1): 51–59. doi:10.1016/0896-6273(93)90241-i. PMID 7678966. S2CID 16011527.
- ^ Tarnawa, István; Farkas, Sándor; Berzsenyi, Pál; Pataki, Ágnes; Andrási, Ferenc (1989). "Electrophysiological studies with a 2,3-benzodiazepine muscle relaxant: GYKI 52466". European Journal of Pharmacology. 167 (2): 193–199. doi:10.1016/0014-2999(89)90579-7. PMID 2574112.
- ^ Rzeski, W.; Turski, L.; Ikonomidou, C. (2001). "Glutamate antagonists limit tumor growth". Proceedings of the National Academy of Sciences. 98 (11): 6372–6377. doi:10.1073/pnas.091113598. PMC 33475. PMID 11331750.
- ^ Paternain, Ana V.; Morales, Miguel; Lerma, Juan (1995). "Selective antagonism of AMPA receptors unmasks kainate receptor-mediated responses in hippocampal neurons". Neuron. 14 (1): 185–189. doi:10.1016/0896-6273(95)90253-8. PMID 7826635. S2CID 6037517.
- ^ Szabados, Tamás; Gigler, Gábor; Gacsályi, István; Gyertyán, István; Lévay, György (2001). "Comparison of anticonvulsive and acute neuroprotective activity of three 2,3-benzodiazepine compounds, GYKI 52466, GYKI 53405, and GYKI 53655". Brain Research Bulletin. 55 (3): 387–391. doi:10.1016/s0361-9230(01)00516-0. PMID 11489346. S2CID 23142293.