Skip to Content
Merck
All Photos(1)

Documents

S4568

Sigma-Aldrich

SCH 58261

≥98% (HPLC), solid

Synonym(s):

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

Sign Into View Organizational & Contract Pricing
All Photos(1)

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

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.
A2A 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

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

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
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
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
View All Related Papers

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service