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S4568

SCH 58261

Name: SCH 58261
Brand: SIGMA

≥98% (HPLC), solid

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Synonym(s):

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

Empirical Formula (Hill Notation):

C₁₈H₁₅N₇O

CAS Number:

160098-96-4

Molecular Weight:

345.36

MDL number:

MFCD00933778

PubChem Substance ID:

329824547

NACRES:

NA.77

Quality Level

100

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

Application

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

Biochem/physiol Actions

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.

A_2A adenosine receptor antagonist.

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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Caffeine and a selective adenosine A2A receptor antagonist induce sensitization and cross-sensitization behavior associated with increased striatal dopamine in mice.

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

Adenosine A2A receptor signaling affects IL-21/IL-22 cytokines and GATA3/T-bet transcription factor expression in CD4

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

Selective adenosine A2A receptor agonists and antagonists protect against spinal cord injury through peripheral and central effects.

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

Selective A

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

Activation of adenosine A2A receptor signaling regulates the expression of cytokines associated with immunologic dysfunction in BTBR T

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

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