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AB120439

SCH-58261, A2A antagonist

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(3 Publications)

MW 345.4 Da, Purity >99%. Potent, highly selective A2A receptor antagonist. (Ki values are 1-2, 289 and >10000 nM at A2A, A1 and A3 receptors, respectively). Displays therapeutic effects in animal Parkinson's models and elicits locomotor sensitization *in vivo*.

View Alternative Names

A1AR, A1R, A2AAR, A2aR, A3AR, A3R, AA1R_HUMAN, AA2AR_HUMAN, AA2BR_HUMAN, AA3R_HUMAN, AD 026, ADENO, ADORA 1, ADORA 2, ADORA 3, ADORA2A, ARA3, Adenosine A2 receptor, Adenosine A2a receptor, Adenosine A3 receptor, Adenosine receptor A1, Adenosine receptor A2a, Adenosine receptor A2b, Adenosine receptor A3, Adenosine receptor subtype A2a, GPCR 2, HGNC:264, Netrin 1 receptor, RDC 7, RDC 8, RP11 552M11.7, Ri, TGPCR1, adora 2b, bA552M11.5, hA2aR

1 Images
Chemical Structure - SCH-58261, A2A antagonist (AB120439)
  • Chemical Structure

Lab

Chemical Structure - SCH-58261, A2A antagonist (AB120439)

2D chemical structure image of ab120439, SCH-58261, A2Aantagonist

Key facts

CAS number

160098-96-4

Purity

>99%

Form

Solid

form

Molecular weight

345.4 Da

Molecular formula

C<sub>1</sub><sub>8</sub>H<sub>1</sub><sub>5</sub>N<sub>7</sub>O

PubChem

176408

Nature

Synthetic

Solubility

Soluble in DMSO to 100 mM

Biochemical name

2-(Furan-2-yl)-7-phenethyl-7H-pyrazolo[4,3-e][1,2,4]triazolo[1,5-c]pyrimidin-5-amine

Biological description

Potent, highly selective A2A receptor antagonist. (Ki values are 1-2, 289 and >10000 nM at A2A, A1 and A3 receptors, respectively). Displays therapeutic effects in animal Parkinson's models and elicits locomotor sensitization *in vivo*.

Canonical smiles

C1=CC=C(C=C1)CCN2C3=C(C=N2)C4=NC(=NN4C(=N3)N)C5=CC=CO5

InChi

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)

InChiKey

UTLPKQYUXOEJIL-UHFFFAOYSA-N

IUPAC Name

4-(furan-2-yl)-10-(2-phenylethyl)-3,5,6,8,10,11-hexazatricyclo[7.3.0.02,6]dodeca-1(9),2,4,7,11-pentaen-7-amine

Properties and storage information

Shipped at conditions
Ambient - Can Ship with Ice
Appropriate short-term storage conditions
Ambient
Appropriate long-term storage conditions
Ambient
Storage information
The product can be stored for up to 12 months

Supplementary information

This supplementary information is collated from multiple sources and compiled automatically.

The adenosine receptor family includes four subtypes: Adenosine A1 Receptor Adenosine Receptor A2a Adenosine A3 Receptor (A3AR) and Adenosine A2b Receptor (ADORA2B). These receptors are G protein-coupled receptors (GPCRs) that each have distinct roles in cellular signaling. They bind adenosine a nucleoside and trigger various downstream effects. For example these receptors are integral to the regulation of myocardial oxygen consumption and cerebral blood flow. They are most commonly expressed in the central nervous system but also show presence in peripheral tissues. Each receptor subtype varies in molecular mass which can influence its interaction with ligands.
Biological function summary

These receptors modulate a wide array of physiological functions. As parts of receptor complexes they influence neurotransmission inflammation and immune responses. Specifically adenosine acts through these receptors to inhibit neurotransmitter release in the brain providing a neuroprotective effect under stress conditions. Adenosine A2a Receptor is known to play a role in vasodilation and immune cell regulation while A3AR has implications in both cardioprotection and cancer biology. These receptors function collectively and independently facilitating cellular communication and maintaining homeostasis.

Pathways

These receptors engage in important signaling cascades such as the cyclic AMP (cAMP) pathway where they either inhibit or stimulate cAMP production through different G proteins. They also participate in MAPK and PI3K/Akt pathways which are critical for cell survival and proliferation. Adenosine Receptor A2a is often studied in relation to dopamine D2 receptors highlighting its role in neuromodulation and potential therapeutic targets for neurological disorders.

Dysfunction of adenosine receptors links to several conditions including cardiovascular diseases and neurological disorders. Changes in adenosine A1 Receptor activity can influence ischemic brain injury recovery while irregularities in Adenosine Receptor A2a activity are associated with chronic inflammatory diseases like asthma. Adenosine receptor activity connects to these diseases through interaction with toll-like receptors and cytokines illustrating an interplay between adenosine signaling and immune response.

Product protocols

Publications (3)

Recent publications for all applications. Explore the full list and refine your search

Cell death discovery 8:475 PubMed36456564

2022

H3K27 tri-demethylase JMJD3 inhibits macrophage apoptosis by promoting ADORA2A in lipopolysaccharide-induced acute lung injury.

Applications

Unspecified application

Species

Unspecified reactive species

Yizhuo Gao,Na Wang,Dong Jia

Theranostics 8:5713-5730 PubMed30555576

2018

Caffeine Protects Skin from Oxidative Stress-Induced Senescence through the Activation of Autophagy.

Applications

Unspecified application

Species

Unspecified reactive species

Yi-Fang Li,Shu-Hua Ouyang,Long-Fang Tu,Xi Wang,Wei-Lin Yuan,Guo-En Wang,Yan-Ping Wu,Wen-Jun Duan,Hong-Min Yu,Zhong-Ze Fang,Hiroshi Kurihara,Youwei Zhang,Rong-Rong He

PloS one 10:e0134488 PubMed26252389

2015

Stimulation of Glia Reveals Modulation of Mammalian Spinal Motor Networks by Adenosine.

Applications

Unspecified application

Species

Unspecified reactive species

David Acton,Gareth B Miles
View all publications

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