IEM-1754 2HBr | CAS#162831-31-4 | open-channel blocker

MedKoo Cat#: 563406 | Name: IEM-1754 2HBr

Description:

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

IEM-1754 2HBr is a voltage-dependent open-channel blocker of AMPA receptors. It acts by selectively blocking GluR2 subunit-lacking (Ca2+-permeable) receptors.

Chemical Structure

IEM-1754 2HBr

CAS#162831-31-4

Theoretical Analysis

MedKoo Cat#: 563406

Name: IEM-1754 2HBr

CAS#: 162831-31-4

Chemical Formula: C16H32Br2N2

Exact Mass:

Molecular Weight: 412.25

Elemental Analysis: C, 46.62; H, 7.82; Br, 38.76; N, 6.80

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Synonym

IEM-1754 dihydrobromide; IEM 1754 dihydrobromide; IEM1754 dihydrobromide; IEM-1754 2HBr; IEM 1754 2HBr; IEM1754 2HBr;

IUPAC/Chemical Name

N-(Tricyclo[3.3.1.13,7]dec-1-ylmethyl)-1,5-pentanediamine dihydrobromide

InChi Key

JMPHTNNJCZDROM-UHFFFAOYSA-N

InChi Code

InChI=1S/C16H30N2.2BrH/c17-4-2-1-3-5-18-12-16-9-13-6-14(10-16)8-15(7-13)11-16;;/h13-15,18H,1-12,17H2;2*1H

SMILES Code

NCCCCCNCC1(C2)CC3CC2CC(C3)C1.[H]Br.[H]Br

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

Shelf Life

>3 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

2934.99.03.00

More Info

Product Data

Product Data

Instruction

View handling instruction

Biological target:

IEM 1754 2HBr is a selective AMPA/kainate receptor blockers for GluR1 and GluR3 with IC50 of 6 μM.

In vitro activity:

The voltage-dependence of IEM-1925 and IEM-1754 action is similar to that of IEM-1460, suggesting that these compounds also behave as weakly-permeant blockers of GluR2-containing AMPAR. Reference: Br J Pharmacol. 2000 Jan;129(2):265-74. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC1571829/

In vivo activity:

The effects of two adamantane derivatives, 1-trimethylammonio-5-(1-adamantane-methyl-ammoniopentane dibromide) (IEM-1460) and 1-ammonio-5-(1-adamantane-methylammoniopentane dibromide) (IEM-1754) on kainate-induced currents were studied in Xenopus oocytes expressing recombinant ionotropic glutamate receptors and in freshly isolated neurones from rat hippocampal slices. In the former cases, IEM-1460 had an IC50 of 1.6 microM at a holding potential (Vh) of -80 mV and IEM-1754 was 3.8 times less potent than IEM-1460. IEM-1460 and IEM-1754 were equipotent when applied to pyramidal neurones, but IEM-1754 was less potent (approximately 3 times) than IEM-1460 when applied to interneurones. Reference: J Physiol. 1997 Dec 15;505 ( Pt 3)(Pt 3):655-63. https://pubmed.ncbi.nlm.nih.gov/9457643/

	Solvent	mg/mL	mM
Solubility
	DMSO	82.0	198.91
	Water	82.0	198.91

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 412.25 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

Formulation protocol:

1. Tikhonov DB, Samoilova MV, Buldakova SL, Gmiro VE, Magazanik LG. Voltage-dependent block of native AMPA receptor channels by dicationic compounds. Br J Pharmacol. 2000 Jan;129(2):265-74. doi: 10.1038/sj.bjp.0703043. PMID: 10694232; PMCID: PMC1571829. 2. Antonov SM, Johnson JW. Voltage-dependent interaction of open-channel blocking molecules with gating of NMDA receptors in rat cortical neurons. J Physiol. 1996 Jun 1;493 ( Pt 2)(Pt 2):425-45. doi: 10.1113/jphysiol.1996.sp021394. PMID: 8782107; PMCID: PMC1158928. 3. Magazanik LG, Buldakova SL, Samoilova MV, Gmiro VE, Mellor IR, Usherwood PN. Block of open channels of recombinant AMPA receptors and native AMPA/kainate receptors by adamantane derivatives. J Physiol. 1997 Dec 15;505 ( Pt 3)(Pt 3):655-63. doi: 10.1111/j.1469-7793.1997.655ba.x. PMID: 9457643; PMCID: PMC1160043.

In vitro protocol:

In vivo protocol:

1. Magazanik LG, Buldakova SL, Samoilova MV, Gmiro VE, Mellor IR, Usherwood PN. Block of open channels of recombinant AMPA receptors and native AMPA/kainate receptors by adamantane derivatives. J Physiol. 1997 Dec 15;505 ( Pt 3)(Pt 3):655-63. doi: 10.1111/j.1469-7793.1997.655ba.x. PMID: 9457643; PMCID: PMC1160043.

1: Vataev SI, Oganesian GA, Lukomskaia NIa, Magazanik LG. [The action of ionotropic glutamate receptor channel blockers on effects of sleep deprivation in rats]. Ross Fiziol Zh Im I M Sechenova. 2013 May;99(5):575-85. Russian. PubMed PMID: 24459868. 2: Vataev SI, Oganesian GA, Gmiro VE, Lukomskaia NIa, Magazanik LG. [Effects of ionotropic glutamate receptor channel blockers ON sleep-waking organization in rats]. Ross Fiziol Zh Im I M Sechenova. 2012 Jul;98(7):809-18. Russian. PubMed PMID: 23074828. 3: Lukomskaia NIa, Vataev SI, Zhabko EP, Magazanik LG. [Effects of ionotropic glutamate receptor channel blockers on the development of audiogenic seizures in Krushinski-Molodkina rats]. Ross Fiziol Zh Im I M Sechenova. 2012 Apr;98(4):449-60. Russian. PubMed PMID: 22834334. 4: Kaczor AA, Kijkowska-Murak UA, Matosiuk D. Theoretical studies on the structure and symmetry of the transmembrane region of glutamatergic GluR5 receptor. J Med Chem. 2008 Jul 10;51(13):3765-76. doi: 10.1021/jm7011694. Epub 2008 Jun 10. PubMed PMID: 18540667. 5: Serdyuk SE, Gmiro VE. Combined blockade of alpha3beta4 nicotinic acetylcholine receptors and GluR1 AMPA receptors in rats prevents kainate-induced tonic-clonic seizures. Bull Exp Biol Med. 2007 May;143(5):611-3. PubMed PMID: 18239782. 6: Lukomskaya NY, Rukoyatkina NI, Gorbunova LV, Gmiro VE, Bol'shakov KV, Magazanik LG. Comparison of the anticonvulsive activities of organic mono- and dications with their abilities to inhibit NMDA and AMPA glutamate receptors. Neurosci Behav Physiol. 2004 Feb;34(2):181-7. PubMed PMID: 15115325. 7: Magazanik LG, Tikhonov DB, Bol'shakov KV, Gmiro VE, Buldakova SL, Samoilova MV. Studies of the structure of glutamate receptor ion channels and the mechanisms of their blockade by organic cations. Neurosci Behav Physiol. 2003 Mar;33(3):237-46. PubMed PMID: 12762590. 8: Lukomskaia NIa, Rukoiatkina NI, Gorbunova LV, Gmiro VE, Bol'shakov KV, Magazanik LG. [Comparison of the anticonvulsant activity of organic mono- and di-cations and their potential to inhibit NMDA and AMPA glutamate receptors]. Ross Fiziol Zh Im I M Sechenova. 2002 Sep;88(9):1161-71. Russian. PubMed PMID: 12503423. 9: Magazanik LG, Tikhonov DB, Bol'shakov KB, Gmiro VE, Buldakova SL, Samoĭlova MV. [Structure of glutamate receptor ion channels and mechanisms of their blockade by organic cations]. Ross Fiziol Zh Im I M Sechenova. 2001 Aug;87(8):1026-39. Russian. PubMed PMID: 11601147. 10: Lukomskaya NY, Zhabko EP, Gmiro VE. The involvement of glutamatergic transmission in the mechanism of movement disorders induced by reversive rotation of white mice. Neurosci Behav Physiol. 2000 Sep-Oct;30(5):543-6. PubMed PMID: 11037145. 11: Rukoiatkina NI, Gorbunova LV, Gmiro VE, Lukomskaia NIa. [Glutamate receptor antagonists attenuate experimental catalepsy in rats]. Ross Fiziol Zh Im I M Sechenova. 2000 Jun;86(6):626-33. Russian. PubMed PMID: 10955300. 12: Gmiro VE, Serdiuk SE. [Bis-ammonium adamantane derivatives--novel modulators of polyamine binding sites]. Eksp Klin Farmakol. 2000 May-Jun;63(3):16-20. Russian. PubMed PMID: 10934589. 13: Gmiro VE, Serdiuk SE. [A comparative study of the central H-cholinergic-blocking and NMDA-blocking actions of MK-801, memantin, amantadine, pyrilen and IEM-1754 in experiments on intact rats]. Eksp Klin Farmakol. 2000 Mar-Apr;63(2):16-20. Russian. PubMed PMID: 10834088. 14: Gmiro VE, Serdiuk SE. [The search for selective blockers of NMDA and AMPA/kainate receptors in a series of bis-ammonium compounds with adamantyl radicals]. Eksp Klin Farmakol. 2000 Jan-Feb;63(1):7-13. Russian. PubMed PMID: 10763102. 15: Tikhonov DB, Samoilova MV, Buldakova SL, Gmiro VE, Magazanik LG. Voltage-dependent block of native AMPA receptor channels by dicationic compounds. Br J Pharmacol. 2000 Jan;129(2):265-74. PubMed PMID: 10694232; PubMed Central PMCID: PMC1571829. 16: Lukomskaia NIa, Zhabko EP, Gmiro VE. [The participation of glutaminergic transmission in the mechanism of movement disorders induced by reverse rotation in white mice]. Ross Fiziol Zh Im I M Sechenova. 1999 Apr;85(4):497-501. Russian. PubMed PMID: 10513382. 17: Antonov SM, Gmiro VE, Johnson JW. Binding sites for permeant ions in the channel of NMDA receptors and their effects on channel block. Nat Neurosci. 1998 Oct;1(6):451-61. PubMed PMID: 10196542. 18: Magazanik LG, Buldakova SL, Samoilova MV, Gmiro VE, Mellor IR, Usherwood PN. Block of open channels of recombinant AMPA receptors and native AMPA/kainate receptors by adamantane derivatives. J Physiol. 1997 Dec 15;505 ( Pt 3):655-63. PubMed PMID: 9457643; PubMed Central PMCID: PMC1160043. 19: Magazanik LG, Samoĭlova MV, Buldakova SL, Esin KV, Gmiro VE. Selective block of AMPA/kainate receptors of hippocampal interneurons as a new approach to the investigation of inhibitory system. Ross Fiziol Zh Im I M Sechenova. 1997 May-Jun;83(5-6):19-39. English, Russian. PubMed PMID: 13677665. 20: Antonov SM, Johnson JW. Voltage-dependent interaction of open-channel blocking molecules with gating of NMDA receptors in rat cortical neurons. J Physiol. 1996 Jun 1;493 ( Pt 2):425-45. PubMed PMID: 8782107; PubMed Central PMCID: PMC1158928.