S4568

SCH 58261

Name: SCH 58261
Brand: SIGMA
Price: 221 USD

≥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

Bioactive Small Molecules

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Show Differences

1 of 4

This Item	C199	S6451	S9311
Sigma-Aldrich S4568 SCH 58261	Sigma-Aldrich C199 CGS-15943	Sigma-Aldrich S6451 SCH-442416	Sigma-Aldrich S9311 SIB 1893
assay ≥98% (HPLC)	assay ≥98% (HPLC)	assay ≥98% (HPLC)	assay >99%
form solid	form solid	form powder	form solid
Quality Level 100	Quality Level 100	Quality Level 100	Quality Level 100
solubility DMSO: soluble >10 mg/mL, H₂O: insoluble	solubility DMSO: >10 mg/mL, H₂O: insoluble	solubility DMSO: ≥20 mg/mL	solubility DMSO: 18 mg/mL
color off-white	color white	color light tan to tan	color -

Application

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

Biochem/physiol Actions

A_2A 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.[1] SCH 58261 increases the concentration of secretion of dopamine and elicits locomotor sensitization, an attractive option in the possible treatment of Parkinson′s disease.[2]

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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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

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

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

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

Neuronal adenosine A2A receptors signal ergogenic effects of caffeine.

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

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SCH 58261