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S6451

Sigma-Aldrich

SCH-442416

≥98% (HPLC)

Synonym(s):

2-(2-Furanyl)-7-[3-(4-methoxyphenyl)propyl]-7H-pyrazolo [4,3-e][1,2,4]triazolo[1,5-c]pyrimidin-5-amine; 5-amino-7-(3-(4-methoxyphenyl)propyl)-2-(2 furyl)pyrazolo[4,3-e]-1,2,4-triazolo[1,5-c]pyrimidine; 5-Amino-7-[3-(4-methoxy)phenylpropyl]-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):
C20H19N7O2
CAS Number:
316173-57-6
Molecular Weight:
389.41
MDL number:
MFCD08703126
UNSPSC Code:
12352200
PubChem Substance ID:
329824564
NACRES:
NA.77

Quality Level

100

Assay

≥98% (HPLC)

form

powder

storage condition

desiccated

color

light tan to tan

solubility

DMSO: ≥20 mg/mL

storage temp.

2-8°C

SMILES string

COc1ccc(CCCn2ncc3c2nc(N)n4nc(nc34)-c5ccco5)cc1

InChI

1S/C20H19N7O2/c1-28-14-8-6-13(7-9-14)4-2-10-26-18-15(12-22-26)19-23-17(16-5-3-11-29-16)25-27(19)20(21)24-18/h3,5-9,11-12H,2,4,10H2,1H3,(H2,21,24)

InChI key

AEULVFLPCJOBCE-UHFFFAOYSA-N

Application

SCH-442416 has been used:
  • as a selective adenosine A2A antagonist to study its effects on cyclic adenosine monophosphate (cAMP) production in T/C-28a2 chondrocytes or hFOB 1.19 osteoblasts 
  • as a presynaptic A2A receptor antagonists to study its effects on receptor blockade on δ9-Tetrahydrocannabinol (THC) self-administration in squirrel monkeys
  • as a presynaptic A2A receptor antagonists to study its effects on cocaine-induced locomotion and cocaine-seeking in mice

Biochem/physiol Actions

SCH-442416 potent and selective Adenosine A2a antagonist. SCH-442416 is >10,000-fold selective for A2a compared to other adensosine receptors.

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

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Certificates of Analysis (COA)

Lot/Batch Number
021M4623V
060M46221V

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Mallikarjunarao Ganesana et al.
PloS one, 13(5), e0196932-e0196932 (2018-05-26)
Adenosine is an important neuromodulator in the central nervous system, and tissue adenosine levels increase during ischemic events, attenuating excitotoxic neuronal injury. Recently, our lab developed an electrochemical fast-scan cyclic voltammetry (FSCV) method that identified rapid, spontaneous changes in adenosine
Fabrizio Vincenzi et al.
PloS one, 8(5), e65561-e65561 (2013-06-07)
Adenosine receptors (ARs) have an important role in the regulation of inflammation and their activation is involved in the inhibition of pro-inflammatory cytokine release. The effects of pulsed electromagnetic fields (PEMFs) on inflammation have been reported and we have demonstrated
Xiaohan Xu et al.
Inflammation research : official journal of the European Histamine Research Society ... [et al.], 66(4), 353-364 (2017-01-12)
Neutrophil chemotaxis plays an essential role in recruiting neutrophils to sites of inflammation. Neutrophil chemotaxis is suppressed both after exposure to lipopolysaccharide (LPS) in vitro and during clinical and experimental endotoxemia, leading to serious consequences. Adenosine (ADO) is a potent
Ying Wang et al.
ACS chemical neuroscience, 10(4), 1941-1949 (2018-09-27)
Adenosine is an endogenous neuroprotectant that modulates vasodilation in the central nervous system. Oxygen changes occur when there is an increase in local cerebral blood flow and thus are a measure of vasodilation. Transient oxygen events following rapid adenosine events
Takahiro Matsuya et al.
Journal of pharmacological sciences, 103(3), 329-332 (2007-03-08)
In this study, we examined the combination effects of L-DOPA and adenosine receptor antagonists on rotational behaviors in a hemi-Parkinsonian mouse model induced by unilateral 6-hydroxydopamine (6-OHDA) injection. The adenosine A(2A) antagonist SCH-58261, but not the A(1)-receptor antagonist 8-cyclopentyl-1,3-dipropylxanthine or
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