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Merck
CN

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
Assay:
≥98% (HPLC)
Form:
solid
Quality level:
100

Key Documents

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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
0000187943
0000187942
0000187943
0000187942
0000126130

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Irene Paterniti et al.
Journal of neuroinflammation, 8, 31-31 (2011-04-14)
Permanent functional deficits following spinal cord injury (SCI) arise both from mechanical injury and from secondary tissue reactions involving inflammation. Enhanced release of adenosine and glutamate soon after SCI represents a component in the sequelae that may be responsible for
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
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
Jing Dong et al.
Molecular neurobiology, 54(5), 3407-3417 (2016-05-15)
Deprivation of spontaneous rhythmic electrical activity in early development by anesthesia administration, among other interventions, induces neuronal apoptosis. However, it is unclear whether enhancement of neuronal electrical activity attenuates neuronal apoptosis in either normal development or after anesthesia exposure. The
Sven Berberich et al.
Scientific reports, 7(1), 17040-17040 (2017-12-08)
Mechanisms underlying information storage have been depicted for global cell-wide and pathway-specific synaptic plasticity. Yet, little is known how these forms of plasticity interact to enhance synaptic competition and network stability. We examined synaptic interactions between apical and basal dendrites
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