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Merck
CN

S4568

Sigma-Aldrich

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
MDL number:
MFCD00933778
UNSPSC Code:
12352200
PubChem Substance ID:
329824547
NACRES:
NA.77

Key Documents

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Product Name

SCH 58261, ≥98% (HPLC), solid

Assay

≥98% (HPLC)

form

solid

color

off-white

solubility

DMSO: soluble >10 mg/mL
H2O: insoluble

SMILES string

Nc1nc2n(CCc3ccccc3)ncc2c4nc(nn14)-c5ccco5

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)

InChI key

UTLPKQYUXOEJIL-UHFFFAOYSA-N

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 Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
0000187943
0000187942
0000187943
0000187942
0000126130

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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
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
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
Chih W Hsu et al.
Journal of biomedical science, 17, 4-4 (2010-01-16)
Caffeine, a nonselective adenosine A1 and A(2A) receptor antagonist, is the most widely used psychoactive substance in the world. Evidence demonstrates that caffeine and selective adenosine A(2A) antagonists interact with the neuronal systems involved in drug reinforcement, locomotor sensitization, and
Thomas Pleli et al.
Cellular physiology and biochemistry : international journal of experimental cellular physiology, biochemistry, and pharmacology, 45(6), 2516-2528 (2018-03-28)
Signaling of Gs protein-coupled receptors (GsPCRs) is accomplished by stimulation of adenylyl cyclase, causing an increase of the intracellular cAMP concentration, activation of the intracellular cAMP effectors protein kinase A (PKA) and Epac, and an efflux of cAMP, the function
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