GYKI 52466 HCl | CAS#192065-56-8 | AMPA receptor antagonist

MedKoo Cat#: 464805 | Name: GYKI 52466 HCl

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Description:

WARNING: This product is for research use only, not for human or veterinary use.

GYKI 52466 is an allosteric AMPA receptor antagonist. It selectively inhibits AMPA-induced inward currents (IC50 = 7.5 µM) over NMDA- or GABA-induced inward currents in primary rat hippocampal neurons at 50 µM but also inhibits kainate-induced inward currents in the same cells (IC50 = 11 µM).2 GYKI 52466 (10 µM) reduces the amplitude of spontaneous excitatory postsynaptic currents (EPSCs) in the same cells. It increases the latency to seizure onset and reduces mortality in a rat model of generalized tonic-clonic seizures induced by 4-aminopyridine (4-AP) when administered at doses of 25 and 50 mg/kg. GYKI 52466 (30 mg/kg) prevents neuronal damage in the CA1 region of the hippocampus in a rat model of global ischemia-reperfusion injury induced by four-vessel occlusion.

Chemical Structure

GYKI 52466 HCl

CAS#192065-56-8 (HCl)

Theoretical Analysis

MedKoo Cat#: 464805

Name: GYKI 52466 HCl

CAS#: 192065-56-8 (HCl)

Chemical Formula: C17H16ClN3O2

Exact Mass: 329.0931

Molecular Weight: 329.78

Elemental Analysis: C, 61.92; H, 4.89; Cl, 10.75; N, 12.74; O, 9.70

Price and Availability

Size	Price	Availability	Quantity
10mg	USD 400.00	2 Weeks
25mg	USD 750.00	2 Weeks

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Related CAS #

192065-56-8 (HCl) 102771-26-6 (free base)

Synonym

GYKI 52466 HCl; GYKI-52466 HCl; GYKI52466 HCl; GYKI 52466 hydrochloride; GYKI52466 hydrochloride; GYKI-52466 hydrochloride;

IUPAC/Chemical Name

4-(8-methyl-9H-[1,3]dioxolo[4',5':4,5]benzo[1,2-d][1,2]diazepin-5-yl)aniline hydrochloride

InChi Key

RUBSCPARMVJNKX-UHFFFAOYSA-N

InChi Code

InChI=1S/C17H15N3O2.ClH/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;1H

SMILES Code

CC1=NN=C(C2=C(C1)C=C3OCOC3=C2)C4=CC=C(C=C4)N.Cl

Appearance

Solid powder

Purity

>98% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility

To be determined

Shelf Life

>2 years if stored properly

Drug Formulation

To be determined

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.9001

More Info

Instruction

View handling instruction

	Solvent	mg/mL	mM	comments
Solubility
	Methanol	1.0	3.03

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 329.78 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

1: John CA, Beart PM, Giardina SF, Pascoe CJ, Cheung NS. Cyclothiazide and GYKI 52466 modulate AMPA receptor-mediated apoptosis in cortical neuronal cultures. Neurosci Lett. 1999 Jun 11;268(1):9-12. doi: 10.1016/s0304-3940(99)00342-0. PMID: 10400065. 2: Kretschmer BD, Kratzer U, Schmidt WJ. Riluzole, a glutamate release inhibitor, and motor behavior. Naunyn Schmiedebergs Arch Pharmacol. 1998 Aug;358(2):181-90. doi: 10.1007/pl00005241. PMID: 9750003. 3: Liljequist S, Cebers G, Kalda A. Effects of decahydroisoquinoline-3-carboxylic acid monohydrate, a novel AMPA receptor antagonist, on glutamate-induced CA2+ responses and neurotoxicity in rat cortical and cerebellar granule neurons. Biochem Pharmacol. 1995 Nov 27;50(11):1761-74. doi: 10.1016/0006-2952(95)02032-2. PMID: 8615854. 4: Hauber W, Waldenmeier MT. The AMPA receptor antagonist GYKI 52466 reverses the anti-cataleptic effects of the competitive NMDA receptor antagonist CGP 37849. Eur J Pharmacol. 1994 May 2;256(3):339-42. doi: 10.1016/0014-2999(94)90561-4. PMID: 7913894. 5: Smith SE, al-Zubaidy ZA, Chapman AG, Meldrum BS. Excitatory amino acid antagonists, lamotrigine and BW 1003C87 as anticonvulsants in the genetically epilepsy-prone rat. Epilepsy Res. 1993 Jun;15(2):101-11. doi: 10.1016/0920-1211(93)90091-k. PMID: 8103738. 6: Chapman AG, al-Zubaidy Z, Meldrum BS. Aniracetam reverses the anticonvulsant action of NBQX and GYKI 52466 in DBA/2 mice. Eur J Pharmacol. 1993 Feb 9;231(2):301-3. doi: 10.1016/0014-2999(93)90465-t. PMID: 8453982. 7: Le Peillet E, Arvin B, Moncada C, Meldrum BS. The non-NMDA antagonists, NBQX and GYKI 52466, protect against cortical and striatal cell loss following transient global ischaemia in the rat. Brain Res. 1992 Jan 31;571(1):115-20. doi: 10.1016/0006-8993(92)90516-c. PMID: 1351775. 8: Moncada C, Arvin B, Le Peillet E, Meldrum BS. Non-NMDA antagonists protect against kainate more than AMPA toxicity in the rat hippocampus. Neurosci Lett. 1991 Dec 9;133(2):287-90. doi: 10.1016/0304-3940(91)90590-p. PMID: 1816508. 9: Smith SE, Dürmüller N, Meldrum BS. The non-N-methyl-D-aspartate receptor antagonists, GYKI 52466 and NBQX are anticonvulsant in two animal models of reflex epilepsy. Eur J Pharmacol. 1991 Aug 29;201(2-3):179-83. doi: 10.1016/0014-2999(91)90342-n. PMID: 1686756.