GYKI 52466

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 GABA_A receptors.^[5] Like other AMPA receptor antagonists, GYKI 52466 has anticonvulsant and neuroprotective properties.^[6]

Quick facts Names, Identifiers ...

GYKI 52466

Names
Preferred IUPAC name 4-(8-Methyl-2H,9H-[1,3]dioxolo[4,5-h][2,3]benzodiazepin-5-yl)aniline
Identifiers
CAS Number	102771-26-6 Y 192065-56-8 (HCl salt) N
3D model (JSmol)	Interactive image
ChEBI	CHEBI:79560 N
ChEMBL	ChEMBL275006 N
ChemSpider	3417 N
ECHA InfoCard	100.162.378
IUPHAR/BPS	4210
KEGG	C15040 N
PubChem CID	3538
UNII	471V8NZ5X3 N
CompTox Dashboard (EPA)	DTXSID40145500
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	293.326 g·mol−1
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). N verify (what is YN ?) Infobox references

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CNS review:^[7]