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Merck

S4568

SCH 58261

≥98% (HPLC), adenosine receptor antagonist, solid

Synonym(s):

7-(2-phenylethyl)-5-amino-2-(2-furyl)-pyrazolo-[4,3-e]-1,2,4-triazolo[1,5-c]pyrimidine

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About This Item

Empirical Formula (Hill Notation):
C18H15N7O
CAS Number:
160098-96-4
Molecular Weight:
345.36
UNSPSC Code:
12352200
PubChem Substance ID:
329824547
NACRES:
NA.77
MDL number:
MFCD00933778

Product Name

SCH 58261, ≥98% (HPLC), solid

SMILES string

Nc1nc2n(CCc3ccccc3)ncc2c4nc(nn14)-c5ccco5

InChI key

UTLPKQYUXOEJIL-UHFFFAOYSA-N

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)

assay

≥98% (HPLC)

form

solid

color

off-white

solubility

DMSO: soluble >10 mg/mL
H2O: insoluble

Quality Level

100

Related Categories

Application

SCH 58261 was used to block A2α adenosine receptor to study the signaling by prostatic acid phosphatase in neurons.4

Biochem/physiol Actions

A2A adenosine receptor antagonist.
SCH 58261 reduces the levels of TNF-α, Fas-L, Bax expression and activation of JNK-MAPK pathway. It has neuroprotective effects as it reduces demyelination of the neurons. SCH 58261 increases the concentration of secretion of dopamine and elicits locomotor sensitization, an attractive option in the possible treatment of Parkinson′s disease.

Features and Benefits

This compound is featured on the Adenosine Receptors page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Certificates of Analysis (COA)

Lot/Batch Number
0000187942
0000187943
0000187942
0000187943
0000126130

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Sheikh F Ahmad et al.
Journal of neuroimmunology, 311, 59-67 (2017-08-16)
Autism is a complex heterogeneous neurodevelopmental disorder; previous studies have identified altered immune responses among individuals diagnosed with autism. An imbalance in the production of pro- and anti-inflammatory cytokines and transcription factors plays a role in neurodevelopmental behavioral and autism
Aderbal S Aguiar et al.
Scientific reports, 10(1), 13414-13414 (2020-08-10)
Caffeine is one of the most used ergogenic aid for physical exercise and sports. However, its mechanism of action is still controversial. The adenosinergic hypothesis is promising due to the pharmacology of caffeine, a nonselective antagonist of adenosine A1 and
Cristiani F Bortolatto et al.
Metabolic brain disease, 32(6), 1919-1927 (2017-08-11)
The aim of the present study was to investigate the effects of SCH58261, a selective adenosine A
Mushtaq A Ansari et al.
Molecular and cellular neurosciences, 82, 76-87 (2017-05-04)
Autism spectrum disorder (ASD) is neurodevelopmental disorders characterized by stereotypical repetitive behavior, impaired social interaction, and deficits in communication. The BTBR T
Siqi Chen et al.
Cancer immunology research, 8(8), 1064-1074 (2020-05-10)
Accumulating evidence suggests that inhibiting adenosine-generating ecto-enzymes (CD39 and CD73) and/or adenosine A2A or A2B receptors (R) stimulates antitumor immunity and limits tumor progression. Although activating A2ARs or A2BRs causes similar immunosuppressive and protumoral functions, few studies have investigated the
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