SCH-58261
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MedKoo CAT#: 526655

CAS#: 160098-96-4

Description: SCH-58261 is a potent and selective adenosine A(2A) receptor antagonist. SCH-58261 is a useful ligand in autoradiographic studies. Blockade of adenosine A2A receptors by SCH 58261 results in neuroprotective effects in cerebral ischaemia in rats. SCH 58261 counteracts parkinsonian-like muscle rigidity in rats. SCH 58261 reduces striatal transmitter outflow, turning behavior and ischemic brain damage induced by permanent focal ischemia in the rat. SCH 58261 protects from neurological deficit, brain damage and activation of p38 MAPK in rat focal cerebral ischemia.


Price and Availability

Size Price Shipping out time Quantity
100mg USD 750 2 Weeks
200mg USD 1250 2 Weeks
500mg USD 2150 2 Weeks
1g USD 3450 2 Weeks
2g USD 4850 2 Weeks
5g USD 7950 2 Weeks
Inquire bulk and customized quantity

Pricing updated 2020-10-26. Prices are subject to change without notice.

SCH-58261, purity > 98%, is in stock. Current shipping out time is about 2 weeks after order is received. CoA, QC data and MSDS documents are available in one week after order is received. Delivery time: overnight (USA/Canada); 3-5 days (worldwide). Shipping fee: from $30.00 (USA); from $45.00 (Canada); from $70.00 (international).


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 526655
Name: SCH-58261
CAS#: 160098-96-4
Chemical Formula: C18H15N7O
Exact Mass: 345.1338
Molecular Weight: 345.366
Elemental Analysis: C, 62.60; H, 4.38; N, 28.39; O, 4.63


Synonym: SCH-58261; SCH 58261; SCH58261.

IUPAC/Chemical Name: 2-(furan-2-yl)-7-phenethyl-7H-pyrazolo[4,3-e][1,2,4]triazolo[1,5-c]pyrimidin-5-amine

InChi Key: UTLPKQYUXOEJIL-UHFFFAOYSA-N

InChi Code: InChI=1S/C18H15N7O/c19-18-22-16-13(11-20-24(16)9-8-12-5-2-1-3-6-12)17-21-15(23-25(17)18)14-7-4-10-26-14/h1-7,10-11H,8-9H2,(H2,19,22)

SMILES Code: NC1=NC(N(CCC2=CC=CC=C2)N=C3)=C3C4=NC(C5=CC=CO5)=NN14


Technical Data

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


References

1: Shah U, Boyle CD, Chackalamannil S, Neustadt BR, Lindo N, Greenlee WJ, Foster C, Arik L, Zhai Y, Ng K, Wang S, Monopoli A, Lachowicz JE. Biaryl and heteroaryl derivatives of SCH 58261 as potent and selective adenosine A2A receptor antagonists. Bioorg Med Chem Lett. 2008 Jul 15;18(14):4199-203. doi: 10.1016/j.bmcl.2008.05.074. Epub 2008 May 22. PubMed PMID: 18562199.

2: Shah U, Lankin CM, Boyle CD, Chackalamannil S, Greenlee WJ, Neustadt BR, Cohen-Williams ME, Higgins GA, Ng K, Varty GB, Zhang H, Lachowicz JE. Design, synthesis, and evaluation of fused heterocyclic analogs of SCH 58261 as adenosine A2A receptor antagonists. Bioorg Med Chem Lett. 2008 Jul 15;18(14):4204-9. doi: 10.1016/j.bmcl.2008.05.069. Epub 2008 May 22. PubMed PMID: 18558486.

3: Domenici MR, Scattoni ML, Martire A, Lastoria G, Potenza RL, Borioni A, Venerosi A, Calamandrei G, Popoli P. Behavioral and electrophysiological effects of the adenosine A2A receptor antagonist SCH 58261 in R6/2 Huntington's disease mice. Neurobiol Dis. 2007 Nov;28(2):197-205. Epub 2007 Jul 24. PubMed PMID: 17720507.

4: Melani A, Gianfriddo M, Vannucchi MG, Cipriani S, Baraldi PG, Giovannini MG, Pedata F. The selective A2A receptor antagonist SCH 58261 protects from neurological deficit, brain damage and activation of p38 MAPK in rat focal cerebral ischemia. Brain Res. 2006 Feb 16;1073-1074:470-80. Epub 2006 Jan 26. PubMed PMID: 16443200.

5: Wardas J. Synergistic effect of SCH 58261, an adenosine A2A receptor antagonist, and L-DOPA on the reserpine-induced muscle rigidity in rats. Pol J Pharmacol. 2003 Mar-Apr;55(2):155-64. PubMed PMID: 12926542.

6: Wardas J, Pietraszek M, Dziedzicka-Wasylewska M. SCH 58261, a selective adenosine A2A receptor antagonist, decreases the haloperidol-enhanced proenkephalin mRNA expression in the rat striatum. Brain Res. 2003 Jul 11;977(2):270-7. PubMed PMID: 12834887.

7: Melani A, Pantoni L, Bordoni F, Gianfriddo M, Bianchi L, Vannucchi MG, Bertorelli R, Monopoli A, Pedata F. The selective A2A receptor antagonist SCH 58261 reduces striatal transmitter outflow, turning behavior and ischemic brain damage induced by permanent focal ischemia in the rat. Brain Res. 2003 Jan 10;959(2):243-50. PubMed PMID: 12493612.

8: Tebano MT, Domenici MR, Popoli P. SCH 58261 differentially influences quinolinic acid-induced effects in striatal and in hippocampal slices. Eur J Pharmacol. 2002 Aug 30;450(3):253-7. PubMed PMID: 12208317.

9: El Yacoubi M, Ledent C, Parmentier M, Ongini E, Costentin J, Vaugeois JM. In vivo labelling of the adenosine A2A receptor in mouse brain using the selective antagonist [3H]SCH 58261. Eur J Neurosci. 2001 Nov;14(9):1567-70. PubMed PMID: 11722618.

10: Pintor A, Quarta D, Pèzzola A, Reggio R, Popoli P. SCH 58261 (an adenosine A(2A) receptor antagonist) reduces, only at low doses, K(+)-evoked glutamate release in the striatum. Eur J Pharmacol. 2001 Jun 15;421(3):177-80. PubMed PMID: 11516434.

11: Wardas J, Konieczny J, Lorenc-Koci E. SCH 58261, an A(2A) adenosine receptor antagonist, counteracts parkinsonian-like muscle rigidity in rats. Synapse. 2001 Aug;41(2):160-71. PubMed PMID: 11400182.

12: Pinna A, Fenu S, Morelli M. Motor stimulant effects of the adenosine A2A receptor antagonist SCH 58261 do not develop tolerance after repeated treatments in 6-hydroxydopamine-lesioned rats. Synapse. 2001 Mar 1;39(3):233-8. PubMed PMID: 11284438.

13: Pinna A, Fenu S, Morelli M. Motor stimulant effects of the adenosine A(2A) receptor antagonist SCH 58261 do not develop tolerance after repeated treatments in 6-hydroxydopamine-lesioned rats. Synapse. 2001 Mar 1;39(2):233-238. PubMed PMID: 11169767.

14: El Yacoubi M, Ledent C, Parmentier M, Costentin J, Vaugeois J. SCH 58261 and ZM 241385 differentially prevent the motor effects of CGS 21680 in mice: evidence for a functional 'atypical' adenosine A(2A) receptor. Eur J Pharmacol. 2000 Jul 28;401(1):63-77. PubMed PMID: 10915839.

15: Popoli P, Reggio R, Pèzzola A. Effects of SCH 58261, an adenosine A(2A) receptor antagonist, on quinpirole-induced turning in 6-hydroxydopamine-lesioned rats. Lack of tolerance after chronic caffeine intake. Neuropsychopharmacology. 2000 May;22(5):522-9. PubMed PMID: 10731627.

16: Ongini E, Dionisotti S, Gessi S, Irenius E, Fredholm BB. Comparison of CGS 15943, ZM 241385 and SCH 58261 as antagonists at human adenosine receptors. Naunyn Schmiedebergs Arch Pharmacol. 1999 Jan;359(1):7-10. PubMed PMID: 9933143.

17: Monopoli A, Lozza G, Forlani A, Mattavelli A, Ongini E. Blockade of adenosine A2A receptors by SCH 58261 results in neuroprotective effects in cerebral ischaemia in rats. Neuroreport. 1998 Dec 1;9(17):3955-9. PubMed PMID: 9875735.

18: Varani K, Gessi S, Dionisotti S, Ongini E, Borea PA. [3H]-SCH 58261 labelling of functional A2A adenosine receptors in human neutrophil membranes. Br J Pharmacol. 1998 Apr;123(8):1723-31. PubMed PMID: 9605581; PubMed Central PMCID: PMC1565317.

19: Monopoli A, Casati C, Lozza G, Forlani A, Ongini E. Cardiovascular pharmacology of the A2A adenosine receptor antagonist, SCH 58261, in the rat. J Pharmacol Exp Ther. 1998 Apr;285(1):9-15. PubMed PMID: 9535988.

20: Fredholm BB, Lindström K, Dionisotti S, Ongini E. [3H]SCH 58261, a selective adenosine A2A receptor antagonist, is a useful ligand in autoradiographic studies. J Neurochem. 1998 Mar;70(3):1210-6. PubMed PMID: 9489743.