GYKI 52466 | CAS#102771-26-6 | AMPA receptor antagonist

MedKoo Cat#: 522535 | Name: GYKI-52466

Description:

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

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.

Chemical Structure

GYKI-52466

CAS#102771-26-6 (free base)

Theoretical Analysis

MedKoo Cat#: 522535

Name: GYKI-52466

CAS#: 102771-26-6 (free base)

Chemical Formula: C17H15N3O2

Exact Mass: 293.1164

Molecular Weight: 293.33

Elemental Analysis: C, 69.61; H, 5.15; N, 14.33; O, 10.91

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.

Bulk Inquiry

Related CAS #

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

Synonym

GYKI-52466; GYKI52466; GYKI 52466; GYKI-5,2466; GYKI52,466; GYKI 52,466; GYKI-2466; GYKI2466; GYKI 2466

IUPAC/Chemical Name

4-(8-methyl-9H-[1,3]dioxolo[4,5-h][2,3]benzodiazepin-5-yl)aniline

InChi Key

LFBZZHVSGAHQPP-UHFFFAOYSA-N

InChi Code

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

SMILES Code

NC1=CC=C(C2=NN=C(C)CC3=CC4=C(OCO4)C=C32)C=C1

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

Soluble in DMSO, not in water

Shelf Life

>2 years if stored properly

Drug Formulation

This drug may be formulated in DMSO

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

Preparing Stock Solutions

The following data is based on the product molecular weight 293.33 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: Nayak PK, Kerr DS. Functional preservation of hippocampal CA1 by low-dose GYKI-52466 preconditioning in a rat model of hypoxic-ischemic brain injury. Brain Res. 2015 Jul 10;1613:100-9. doi: 10.1016/j.brainres.2015.04.004. Epub 2015 Apr 11. PubMed PMID: 25869178. 2: Wu A, Wang C, Niu L. Mechanism of inhibition of the GluA1 AMPA receptor channel opening by the 2,3-benzodiazepine compound GYKI 52466 and a N-methyl-carbamoyl derivative. Biochemistry. 2014 May 13;53(18):3033-41. doi: 10.1021/bi5002079. Epub 2014 May 1. PubMed PMID: 24738995; PubMed Central PMCID: PMC4025570. 3: Nayak PK, Kerr DS. Low-dose GYKI-52466: prophylactic preconditioning confers long-term neuroprotection and functional recovery following hypoxic-ischaemic brain injury. Neuroscience. 2013 Mar 1;232:128-38. doi: 10.1016/j.neuroscience.2012.11.063. Epub 2012 Dec 16. PubMed PMID: 23246617. 4: Srivastava R, Xi ZX, Gardner EL. Cocaine-taking and cocaine-seeking behaviors in rats remain stable after systemic administration of GYKI 52466: a non-competitive AMPA receptor antagonist. Neurosci Lett. 2012 Feb 6;508(2):106-9. doi: 10.1016/j.neulet.2011.12.028. Epub 2011 Dec 22. PubMed PMID: 22206835; PubMed Central PMCID: PMC3267379. 5: Goulton CS, Patten AR, Kerr JR, Kerr DS. Pharmacological Preconditioning with GYKI 52466: A Prophylactic Approach to Neuroprotection. Front Neurosci. 2010 Aug 3;4. pii: 54. doi: 10.3389/fnins.2010.00054. eCollection 2010. PubMed PMID: 20953290; PubMed Central PMCID: PMC2955399. 6: Nandhu MS, Paul J, Mathew J, Peeyush Kumar T, Paulose CS. GYKI-52466: a potential therapeutic agent for glutamate-mediated excitotoxic injury in Cerebral Palsy. Med Hypotheses. 2010 Mar;74(3):619-20. doi: 10.1016/j.mehy.2009.10.033. Epub 2009 Nov 13. PubMed PMID: 19914009. 7: Colak A, Soy O, Karaoglan A, Akdemir O, Kokturk S, Sagmanligil A, Tasyurekli M. Effects of GYKI 52466 on early vasospasm in rats. Cent Eur Neurosurg. 2009 Nov;70(4):187-94. doi: 10.1055/s-0029-1202357. Epub 2009 Oct 22. PubMed PMID: 19851958. 8: Fritsch B, Stott JJ, Joelle Donofrio J, Rogawski MA. Treatment of early and late kainic acid-induced status epilepticus with the noncompetitive AMPA receptor antagonist GYKI 52466. Epilepsia. 2010 Jan;51(1):108-17. doi: 10.1111/j.1528-1167.2009.02205.x. Epub 2009 Jul 20. PubMed PMID: 19682025; PubMed Central PMCID: PMC4535693. 9: Kapus GL, Gacsályi I, Vegh M, Kompagne H, Hegedus E, Leveleki C, Hársing LG, Barkóczy J, Bilkei-Gorzó A, Lévay G. Antagonism of AMPA receptors produces anxiolytic-like behavior in rodents: effects of GYKI 52466 and its novel analogues. Psychopharmacology (Berl). 2008 Jun;198(2):231-41. doi: 10.1007/s00213-008-1121-z. Epub 2008 Mar 25. PubMed PMID: 18363046. 10: O'Hearn E, Molliver ME. Administration of a non-NMDA antagonist, GYKI 52466, increases excitotoxic Purkinje cell degeneration caused by ibogaine. Neuroscience. 2004;127(2):373-83. PubMed PMID: 15262328. 11: Jakus R, Graf M, Ando RD, Balogh B, Gacsalyi I, Levay G, Kantor S, Bagdy G. Effect of two noncompetitive AMPA receptor antagonists GYKI 52466 and GYKI 53405 on vigilance, behavior and spike-wave discharges in a genetic rat model of absence epilepsy. Brain Res. 2004 May 22;1008(2):236-44. PubMed PMID: 15145761. 12: Colak A, Soy O, Uzun H, Aslan O, Barut S, Belce A, Akyildiz A, Taşyürekli M. Neuroprotective effects of GYKI 52466 on experimental spinal cord injury in rats. J Neurosurg. 2003 Apr;98(3 Suppl):275-81. PubMed PMID: 12691384. 13: Tutka P, Olszewski K, Woźniak M, Kleinrok Z, Czuczwar SJ, Wielosz M. Molsidomine potentiates the protective activity of GYKI 52466, a non-NMDA antagonist, MK-801, a non-competitive NMDA antagonist, and riluzole against electroconvulsions in mice. Eur Neuropsychopharmacol. 2002 Aug;12(4):321-6. PubMed PMID: 12126871. 14: Rakovska A, Kiss JP, Raichev P, Lazarova M, Kalfin R, Djambazova E. The non-competitive AMPA receptor antagonist (GYKI 52466) blocks quisqualate-induced acetylcholine release from the rat hippocampus and striatum: an in vivo microdialysis study. Neurochem Int. 2002 Apr;40(5):419-26. PubMed PMID: 11821149. 15: Borowicz KK, Duda AM, Kleinrok Z, Czuczwar SJ. Interaction of GYKI 52466, a selective non-competitive antagonist of AMPA/kainate receptors, with conventional antiepileptic drugs in amygdala-kindled seizures in rats. Pol J Pharmacol. 2001 Mar-Apr;53(2):101-8. PubMed PMID: 11787948. 16: Szabados T, Gigler G, Gacsályi I, Gyertyán I, Lévay G. Comparison of anticonvulsive and acute neuroprotective activity of three 2,3-benzodiazepine compounds, GYKI 52466, GYKI 53405, and GYKI 53655. Brain Res Bull. 2001 Jun;55(3):387-91. PubMed PMID: 11489346. 17: Arai AC. GYKI 52466 has positive modulatory effects on AMPA receptors. Brain Res. 2001 Feb 23;892(2):396-400. PubMed PMID: 11172790. 18: Lees GJ, Leong W. In vivo, the direct and seizure-induced neuronal cytotoxicity of kainate and AMPA is modified by the non-competitive antagonist, GYKI 52466. Brain Res. 2001 Jan 26;890(1):66-77. PubMed PMID: 11164769. 19: Glade U, Häfker T, Motzko D, Flohr H. [The non-competitive AMPA antagonist GYKI 52466 increases the anesthetic efficacy of methohexital]. Anasthesiol Intensivmed Notfallmed Schmerzther. 2000 Sep;35(9):597-8. German. PubMed PMID: 11050968. 20: Arai AC, Kessler M, Rogers G, Lynch G. Effects of the potent ampakine CX614 on hippocampal and recombinant AMPA receptors: interactions with cyclothiazide and GYKI 52466. Mol Pharmacol. 2000 Oct;58(4):802-13. PubMed PMID: 10999951.