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Description: Selective A2A antagonist. Also MAO-B inhibitor
Alternative Names: CSC
Chemical Name: (E)-8-[2-(3-Chlorophenyl)ethenyl]-3,7-dihydro-1,3,7-trimethyl-1H-purine-2,6-dione
Purity: ≥99% (HPLC)
Citations (5)
Literature (1)

Biological Activity for 8-(3-Chlorostyryl)caffeine

8-(3-Chlorostyryl)caffeine is a selective adenosine A2A receptor antagonist and monoamine oxidase B (MAO-B) inhibitor (Ki values are 54 and 28200 nM at rat A2A and A1 receptors respectively and Ki ~ 100 nM at MAO-B). Potently protects against quinolinic acid-induced (Cat. No. 0225) neuronal damage and is neuroprotective in the MPTP model of Parkinson's disease.

Technical Data for 8-(3-Chlorostyryl)caffeine

M. Wt 330.77
Formula C16H15ClN4O2
Storage Store at -20°C
Purity ≥99% (HPLC)
CAS Number 147700-11-6
PubChem ID 5353365
Smiles ClC1=CC(/C=C/C(N3C)=NC2=C3C(N(C)C(N2C)=O)=O)=CC=C1

The technical data provided above is for guidance only. For batch specific data refer to the Certificate of Analysis.

Tocris products are intended for laboratory research use only, unless stated otherwise.

Solubility Data for 8-(3-Chlorostyryl)caffeine

Solvent Max Conc. mg/mL Max Conc. mM
DMSO 8.27 25

Preparing Stock Solutions for 8-(3-Chlorostyryl)caffeine

The following data is based on the product molecular weight 330.77. Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Select a batch to recalculate based on the batch molecular weight:
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
0.25 mM 12.09 mL 60.46 mL 120.93 mL
1.25 mM 2.42 mL 12.09 mL 24.19 mL
2.5 mM 1.21 mL 6.05 mL 12.09 mL
12.5 mM 0.24 mL 1.21 mL 2.42 mL

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Product Datasheets for 8-(3-Chlorostyryl)caffeine

References for 8-(3-Chlorostyryl)caffeine

References are publications that support the biological activity of the product.

Chen et al (2002) 8-(3-Chlorostyryl)caffeine may attenuate MPTP neurotoxicity through dual actions on monoamine oxidase inhibition and A2A receptor antagonism. J.Biol.Chem. 277 36040 PMID: 12130655

Behan and Stone (2002) Enhanced neuronal damage by co-administration of quinolinic acid and free radicals, and protection by adenosine A2A receptor antagonists. Br.J.Pharmacol. 135 1435 PMID: 11906956

Vlok et al (2006) Inhibition of monoamine oxidase B by analogues of the adenosine A2A receptor antagonist (E)-8-(3-chlorostyryl)caffeine (CSC). Bioorg.Med.Chem. 14 3512 PMID: 16442801

If you know of a relevant reference for 8-(3-Chlorostyryl)caffeine, please let us know.

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Keywords: 8-(3-Chlorostyryl)caffeine, 8-(3-Chlorostyryl)caffeine supplier, Selective, A2A, antagonists, MAO-B, inhibitors, inhibits, Receptors, adenosines, Monoamine, Oxygenases, Oxidases, CSC, Adenosine, Oxidase, 5-HT-Related, Adrenergic, Related, Compounds, Dopaminergic-Related, 5-HT3, 3306, Tocris Bioscience

5 Citations for 8-(3-Chlorostyryl)caffeine

Citations are publications that use Tocris products. Selected citations for 8-(3-Chlorostyryl)caffeine include:

Benada et al (2015) Polo-like kinase 1 inhibits DNA damage response during mitosis. Oncotarget 14 219 PMID: 25607646

Li et al (2014) Regulation of photoreceptor gap junction phosphorylation by adenosine in zebrafish retina. Vis Neurosci 31 237 PMID: 24844306

Kleiner et al (2018) Activator protein-1 contributes to the NaCl-induced expression of VEGF and PlGF in RPE cells. Mol Vis 24 647 PMID: 30310263

Bao et al (2013) Pannexin 1 channels link chemoattractant receptor signaling to local excitation and global inhibition responses at the front and back of polarized neutrophils. J Biol Chem 288 22650 PMID: 23798685

Factor et al (2007) Adenosine regulation of alveolar fluid clearance. Cell Cycle 104 4083 PMID: 17360481

Do you know of a great paper that uses 8-(3-Chlorostyryl)caffeine from Tocris? Please let us know.

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Literature in this Area

Tocris offers the following scientific literature in this area to showcase our products. We invite you to request* your copy today!

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Parkinson's Disease Poster

Parkinson's Disease Poster

Parkinson's disease (PD) causes chronic disability and is the second most common neurodegenerative condition. This poster outlines the neurobiology of the disease, as well as highlighting current therapeutic treatments for symptomatic PD, and emerging therapeutic strategies to delay PD onset and progression.