GYKI-52,466

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GYKI-52,466

GYKI-52,466[[CITE|1|https://openlibrary.org/search?q=Donevan%2C%20S.D.%2C%20Rogawski%2C%20M.A.%2C%20Allosteric%20regulati]][[CITE|2|https://openlibrary.org/search?q=Donevan%2C%20S.D.%2C%20Rogawski%2C%20M.A.%2C%20GYKI%2052466%2C%20a%202%2C3-b]][[CITE|3|https://openlibrary.org/search?q=Wilding%2C%20T.J.%2C%20Huettner%2C%20J.E.%2C%20Differential%20antago]][[CITE|4|https://openlibrary.org/search?q=Tarnawa%20et%20al.%20%281989%29%20Electrophysiological%20studies]][[CITE|5|https://openlibrary.org/search?q=Paternain%20et%20al.%20%281995%29%20Selective%20antagonism%20of%20AM]][[CITE|6|https://openlibrary.org/search?q=Rzeski%20et%20al.%20%282001%29%20Glutamate%20antagonists%20limit%20t]][[CITE|7|https://openlibrary.org/search?q=Szabados%20et%20al.%20%282001%29%20Comparison%20of%20anticonvulsiv]]
Names

IUPAC name 4-(8-methyl-9H-[1,3]dioxolo[4,5-h][2,3]benzodiazepin-5-yl)aniline
Identifiers
CAS Number	102771-26-6 ^[19]^Y 192065-56-8 ^[20](HCl salt)^N
3D model (JSmol)	Interactive image ^[21]
ChEBI	CHEBI:79560 ^[22]^N
ChEMBL	ChEMBL275006 ^[23]^N
ChemSpider	3417 ^[24]^N
ECHA InfoCard	100.162.378 ^[25]
IUPHAR/BPS	4210 ^[26]
KEGG	C15040 ^[27]^N
PubChemCID	3538 ^[28]
UNII	471V8NZ5X3 ^[29]^N
CompTox Dashboard(EPA)	DTXSID40145500 ^[30]
InChI InChI=1S/C17H15N3O2/c1-10-6-12-7-15-16(22-9-21-15)8-14(12)17(20-19-10)11-2-4-13(18)5-3-11/h2-5,7-8H,6,9,18H2,1H3^N Key: LFBZZHVSGAHQPP-UHFFFAOYSA-N^N InChI=1/C17H15N3O2/c1-10-6-12-7-15-16(22-9-21-15)8-14(12)17(20-19-10)11-2-4-13(18)5-3-11/h2-5,7-8H,6,9,18H2,1H3 Key: LFBZZHVSGAHQPP-UHFFFAOYAH
SMILES CC1=NN=C(C2=CC3=C(C=C2C1)OCO3)C4=CC=C(C=C4)N
Properties
Chemical formula	C₁₇H₁₅N₃O₂
Molar mass	293.32 g/mol
Appearance	Yellow solid (HCl salt)
Density	1.393 g/cm³
Solubility in water	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).
Nverify ^[31] (what is^YN ?)
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.

GYKI-52,466[[CITE|1|https://openlibrary.org/search?q=Donevan%2C%20S.D.%2C%20Rogawski%2C%20M.A.%2C%20Allosteric%20regulati]][[CITE|2|https://openlibrary.org/search?q=Donevan%2C%20S.D.%2C%20Rogawski%2C%20M.A.%2C%20GYKI%2052466%2C%20a%202%2C3-b]][[CITE|3|https://openlibrary.org/search?q=Wilding%2C%20T.J.%2C%20Huettner%2C%20J.E.%2C%20Differential%20antago]][[CITE|4|https://openlibrary.org/search?q=Tarnawa%20et%20al.%20%281989%29%20Electrophysiological%20studies]][[CITE|5|https://openlibrary.org/search?q=Paternain%20et%20al.%20%281995%29%20Selective%20antagonism%20of%20AM]][[CITE|6|https://openlibrary.org/search?q=Rzeski%20et%20al.%20%282001%29%20Glutamate%20antagonists%20limit%20t]][[CITE|7|https://openlibrary.org/search?q=Szabados%20et%20al.%20%282001%29%20Comparison%20of%20anticonvulsiv]]
Names

IUPAC name 4-(8-methyl-9H-[1,3]dioxolo[4,5-h][2,3]benzodiazepin-5-yl)aniline
Identifiers
CAS Number	102771-26-6 ^[19]^Y 192065-56-8 ^[20](HCl salt)^N
3D model (JSmol)	Interactive image ^[21]
ChEBI	CHEBI:79560 ^[22]^N
ChEMBL	ChEMBL275006 ^[23]^N
ChemSpider	3417 ^[24]^N
ECHA InfoCard	100.162.378 ^[25]
IUPHAR/BPS	4210 ^[26]
KEGG	C15040 ^[27]^N
PubChemCID	3538 ^[28]
UNII	471V8NZ5X3 ^[29]^N
CompTox Dashboard(EPA)	DTXSID40145500 ^[30]
InChI InChI=1S/C17H15N3O2/c1-10-6-12-7-15-16(22-9-21-15)8-14(12)17(20-19-10)11-2-4-13(18)5-3-11/h2-5,7-8H,6,9,18H2,1H3^N Key: LFBZZHVSGAHQPP-UHFFFAOYSA-N^N InChI=1/C17H15N3O2/c1-10-6-12-7-15-16(22-9-21-15)8-14(12)17(20-19-10)11-2-4-13(18)5-3-11/h2-5,7-8H,6,9,18H2,1H3 Key: LFBZZHVSGAHQPP-UHFFFAOYAH
SMILES CC1=NN=C(C2=CC3=C(C=C2C1)OCO3)C4=CC=C(C=C4)N
Properties
Chemical formula	C₁₇H₁₅N₃O₂
Molar mass	293.32 g/mol
Appearance	Yellow solid (HCl salt)
Density	1.393 g/cm³
Solubility in water	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).
Nverify ^[31] (what is^YN ?)
Infobox references

References

[1]

Citation Linkopenlibrary.orgDonevan, 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)

Sep 30, 2019, 5:10 AM

[2]

Citation Linkopenlibrary.orgDonevan, 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)

Sep 30, 2019, 5:10 AM

[3]

Citation Linkopenlibrary.orgWilding, 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)

Sep 30, 2019, 5:10 AM

[4]

Citation Linkopenlibrary.orgTarnawa et al. (1989) Electrophysiological studies with a 2,3-benzodiazepine muscle relaxant: GYKI 52466. Eur. J.Pharmacol. 167 193

Sep 30, 2019, 5:10 AM

[5]

Citation Linkopenlibrary.orgPaternain et al. (1995) Selective antagonism of AMPA receptors unmasks kainate receptor-mediated responses in hippocampal neurons. Neuron 14 185.

Sep 30, 2019, 5:10 AM

[6]

Citation Linkopenlibrary.orgRzeski et al. (2001) Glutamate antagonists limit tumor growth. Proc. Natl.Acad. Sci.USA 98 6372.

Sep 30, 2019, 5:10 AM

[7]

Citation Linkopenlibrary.orgSzabados 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.

Sep 30, 2019, 5:10 AM

[8]

Citation Linkwww.commonchemistry.org102771-26-6

Sep 30, 2019, 5:10 AM

[9]

Citation Linkwww.commonchemistry.org192065-56-8

Sep 30, 2019, 5:10 AM

[10]

Citation Linkchemapps.stolaf.eduInteractive image

Sep 30, 2019, 5:10 AM

[11]

Citation Linkwww.ebi.ac.ukCHEBI:79560