A 582941 | CAS#848591-90-2

MedKoo Cat#: 558770 | Name: A 582941

Featured

Description:

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

A-582941 exhibits high-affinity binding and agonism at alpha-7 nicotinic acetylcholine receptor , with pharmacokinetic properties and excellent distribution to the central nervous system. A-582941 activates signaling pathways known to be involved in cognitive functions (ERK1/2 and CREB phosphorylation).

Chemical Structure

A 582941

CAS#848591-90-2 (free base)

Theoretical Analysis

MedKoo Cat#: 558770

Name: A 582941

CAS#: 848591-90-2 (free base)

Chemical Formula: C17H20N4

Exact Mass: 280.1700

Molecular Weight: 280.38

Elemental Analysis: C, 72.83; H, 7.19; N, 19.98

Price and Availability

Size	Price	Availability	Quantity
10mg	USD 450.00	2 Weeks
50mg	USD 1,450.00	2 Weeks

Bulk Inquiry

Buy Now

Add to Cart

Related CAS #

848591-90-2 (free base)

Synonym

A582941, A-582941; A 582941

IUPAC/Chemical Name

(3aR,6aS)-2-methyl-5-(6-phenylpyridazin-3-yl)octahydropyrrolo[3,4-c]pyrrole

InChi Key

GTMRUYCIJSNXGB-GASCZTMLSA-N

InChi Code

InChI=1S/C17H20N4/c1-20-9-14-11-21(12-15(14)10-20)17-8-7-16(18-19-17)13-5-3-2-4-6-13/h2-8,14-15H,9-12H2,1H3/t14-,15+

SMILES Code

[H][C@@]12[C@@](CN(C3=CC=C(C4=CC=CC=C4)N=N3)C2)([H])CN(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

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

2934.99.9001

More Info

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 280.38 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: Tietje KR, Anderson DJ, Bitner RS, Blomme EA, Brackemeyer PJ, Briggs CA, Browman KE, Bury D, Curzon P, Drescher KU, Frost JM, Fryer RM, Fox GB, Gronlien JH, Håkerud M, Gubbins EJ, Halm S, Harris R, Helfrich RJ, Kohlhaas KL, Law D, Malysz J, Marsh KC, Martin RL, Meyer MD, Molesky AL, Nikkel AL, Otte S, Pan L, Puttfarcken PS, Radek RJ, Robb HM, Spies E, Thorin-Hagene K, Waring JF, Ween H, Xu H, Gopalakrishnan M, Bunnelle WH. Preclinical characterization of A-582941: a novel alpha7 neuronal nicotinic receptor agonist with broad spectrum cognition- enhancing properties. CNS Neurosci Ther. 2008 Spring;14(1):65-82. doi: 10.1111/j.1527-3458.2008.00037.x. PMID: 18482100; PMCID: PMC6494002. 2: Leung K. 2-[11C]Methyl-5-[6-phenylpyridazine-3-yl]octahydropyrrolo [3,4-c]pyrrole. 2010 Oct 12 [updated 2011 Jan 14]. In: Molecular Imaging and Contrast Agent Database (MICAD) [Internet]. Bethesda (MD): National Center for Biotechnology Information (US); 2004–2013. PMID: 21290619. 3: Toyohara J, Ishiwata K, Sakata M, Wu J, Nishiyama S, Tsukada H, Hashimoto K. In vivo evaluation of alpha7 nicotinic acetylcholine receptor agonists [11C]A-582941 and [11C]A-844606 in mice and conscious monkeys. PLoS One. 2010 Feb 1;5(2):e8961. doi: 10.1371/journal.pone.0008961. PMID: 20126539; PMCID: PMC2813863. 4: Thomsen MS, Mikkelsen JD, Timmermann DB, Peters D, Hay-Schmidt A, Martens H, Hansen HH. The selective alpha7 nicotinic acetylcholine receptor agonist A-582941 activates immediate early genes in limbic regions of the forebrain: Differential effects in the juvenile and adult rat. Neuroscience. 2008 Jun 23;154(2):741-53. doi: 10.1016/j.neuroscience.2008.03.083. Epub 2008 Apr 16. PMID: 18495359. 5: Buccafusco JJ, Terry AV Jr, Decker MW, Gopalakrishnan M. Profile of nicotinic acetylcholine receptor agonists ABT-594 and A-582941, with differential subtype selectivity, on delayed matching accuracy by young monkeys. Biochem Pharmacol. 2007 Oct 15;74(8):1202-11. doi: 10.1016/j.bcp.2007.07.010. Epub 2007 Jul 14. PMID: 17706609. 6: Potasiewicz A, Kos T, Ravazzini F, Puia G, Arias HR, Popik P, Nikiforuk A. Pro-cognitive activity in rats of 3-furan-2-yl-N-p-tolyl-acrylamide, a positive allosteric modulator of the α7 nicotinic acetylcholine receptor. Br J Pharmacol. 2015 Nov;172(21):5123-35. doi: 10.1111/bph.13277. Epub 2015 Oct 10. Erratum in: Br J Pharmacol. 2016 Jan;173(2):411. PMID: 26276349; PMCID: PMC4687805. 7: Nikiforuk A, Kos T, Hołuj M, Potasiewicz A, Popik P. Positive allosteric modulators of alpha 7 nicotinic acetylcholine receptors reverse ketamine-induced schizophrenia-like deficits in rats. Neuropharmacology. 2016 Feb;101:389-400. doi: 10.1016/j.neuropharm.2015.07.034. Epub 2015 Jul 29. PMID: 26232639. 8: Kohlhaas KL, Bitner RS, Gopalakrishnan M, Rueter LE. Effects of α7 nicotinic acetylcholine receptor agonists on antipsychotic efficacy in a preclinical mouse model of psychosis. Psychopharmacology (Berl). 2012 Apr;220(4):823-33. doi: 10.1007/s00213-011-2535-6. Epub 2011 Oct 29. PMID: 22038534. 9: Unal G, Sirvanci S, Aricioglu F. α7 nicotinic receptor agonist and positive allosteric modulators differently improved schizophrenia-like cognitive deficits in male rats. Behav Brain Res. 2021 Jan 15;397:112946. doi: 10.1016/j.bbr.2020.112946. Epub 2020 Oct 1. PMID: 33011186. 10: Bitner RS, Nikkel AL, Markosyan S, Otte S, Puttfarcken P, Gopalakrishnan M. Selective alpha7 nicotinic acetylcholine receptor activation regulates glycogen synthase kinase3beta and decreases tau phosphorylation in vivo. Brain Res. 2009 Apr 10;1265:65-74. doi: 10.1016/j.brainres.2009.01.069. Epub 2009 Feb 20. PMID: 19230830. 11: Christensen DZ, Mikkelsen JD, Hansen HH, Thomsen MS. Repeated administration of alpha7 nicotinic acetylcholine receptor (nAChR) agonists, but not positive allosteric modulators, increases alpha7 nAChR levels in the brain. J Neurochem. 2010 Aug;114(4):1205-16. doi: 10.1111/j.1471-4159.2010.06845.x. Epub 2010 Jun 1. PMID: 20533993. 12: Thomsen MS, Mikkelsen JD. Type I and II positive allosteric modulators differentially modulate agonist-induced up-regulation of α7 nicotinic acetylcholine receptors. J Neurochem. 2012 Oct;123(1):73-83. doi: 10.1111/j.1471-4159.2012.07876.x. Epub 2012 Aug 16. PMID: 22804734. 13: Thomsen MS, El-Sayed M, Mikkelsen JD. Differential immediate and sustained memory enhancing effects of alpha7 nicotinic receptor agonists and allosteric modulators in rats. PLoS One. 2011;6(11):e27014. doi: 10.1371/journal.pone.0027014. Epub 2011 Nov 9. PMID: 22096516; PMCID: PMC3212529. 14: Bitner RS, Bunnelle WH, Anderson DJ, Briggs CA, Buccafusco J, Curzon P, Decker MW, Frost JM, Gronlien JH, Gubbins E, Li J, Malysz J, Markosyan S, Marsh K, Meyer MD, Nikkel AL, Radek RJ, Robb HM, Timmermann D, Sullivan JP, Gopalakrishnan M. Broad-spectrum efficacy across cognitive domains by alpha7 nicotinic acetylcholine receptor agonism correlates with activation of ERK1/2 and CREB phosphorylation pathways. J Neurosci. 2007 Sep 26;27(39):10578-87. doi: 10.1523/JNEUROSCI.2444-07.2007. PMID: 17898229; PMCID: PMC6673141. 15: Medeiros R, Castello NA, Cheng D, Kitazawa M, Baglietto-Vargas D, Green KN, Esbenshade TA, Bitner RS, Decker MW, LaFerla FM. α7 Nicotinic receptor agonist enhances cognition in aged 3xTg-AD mice with robust plaques and tangles. Am J Pathol. 2014 Feb;184(2):520-9. doi: 10.1016/j.ajpath.2013.10.010. Epub 2013 Nov 19. PMID: 24269557. 16: Tanibuchi Y, Wu J, Toyohara J, Fujita Y, Iyo M, Hashimoto K. Characterization of [(3)H]CHIBA-1001 binding to alpha7 nicotinic acetylcholine receptors in the brain from rat, monkey, and human. Brain Res. 2010 Aug 12;1348:200-8. doi: 10.1016/j.brainres.2010.06.008. Epub 2010 Jun 9. PMID: 20537987. 17: Redrobe JP, Nielsen EØ, Christensen JK, Peters D, Timmermann DB, Olsen GM. Alpha7 nicotinic acetylcholine receptor activation ameliorates scopolamine- induced behavioural changes in a modified continuous Y-maze task in mice. Eur J Pharmacol. 2009 Jan 5;602(1):58-65. doi: 10.1016/j.ejphar.2008.09.035. Epub 2008 Sep 30. PMID: 18848931. 18: Hu M, Waring JF, Gopalakrishnan M, Li J. Role of GSK-3beta activation and alpha7 nAChRs in Abeta(1-42)-induced tau phosphorylation in PC12 cells. J Neurochem. 2008 Aug;106(3):1371-7. doi: 10.1111/j.1471-4159.2008.05483.x. Epub 2008 May 15. PMID: 18485099. 19: Briggs CA, Grønlien JH, Curzon P, Timmermann DB, Ween H, Thorin-Hagene K, Kerr P, Anderson DJ, Malysz J, Dyhring T, Olsen GM, Peters D, Bunnelle WH, Gopalakrishnan M. Role of channel activation in cognitive enhancement mediated by alpha7 nicotinic acetylcholine receptors. Br J Pharmacol. 2009 Nov;158(6):1486-94. doi: 10.1111/j.1476-5381.2009.00426.x. Epub 2009 Oct 20. PMID: 19845675; PMCID: PMC2795215. 20: Wichern F, Jensen MM, Christensen DZ, Mikkelsen JD, Gondré-Lewis MC, Thomsen MS. Perinatal nicotine treatment induces transient increases in NACHO protein levels in the rat frontal cortex. Neuroscience. 2017 Mar 27;346:278-283. doi: 10.1016/j.neuroscience.2017.01.026. Epub 2017 Jan 25. PMID: 28131622; PMCID: PMC5360531.