An adenosine A2 receptor antagonist
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8-(3-Chlorostyryl)caffeine

Item No. 29704

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
8-[(1E)-2-(3-chlorophenyl)ethenyl]-3,7-dihydro-1,3,7-trimethyl-1H-purine-2,6-dione
CAS Number
147700-11-6
Synonyms
  • CSC
Molecular Formula
C16H15ClN4O2
Formula Weight
330.8
Purity
≥95%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
DMSO: 25 mMMethanol: Soluble
SMILES
O=C(N(C)C1=C2N(C)C(/C=C/C3=CC=CC(Cl)=C3)=N1)N(C)C2=O
InChi Code
InChI=1S/C16H15ClN4O2/c1-19-12(8-7-10-5-4-6-11(17)9-10)18-14-13(19)15(22)21(3)16(23)20(14)2/h4-9H,1-3H3/b8-7+
InChi Key
WBWFIUAVMCNYPG-BQYQJAHWSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    10 mg

    $85

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    25 mg

    $202

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    100 mg

    $765

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    Product Description

    8-(3-Chlorostyryl)caffeine (CSC) is an adenosine A2 receptor antagonist (Ki = 54 nM).1 It is selective for adenosine A2 over A1 receptors (Ki = 28 µM). CSC reverses locomotor depression induced by the adenosine A2A agonist APEC in mice (ED50 = 16 µg/kg, i.p.). It increases locomotion in mice when administered at a dose of 5 mg/kg. CSC (5 mg/kg) reverses the shortening of the rotational motor response and increases in striatal adenosine A2 receptor levels induced by L-DOPA (Item No. 13248) in a rat model of Parkinson’s disease induced by 6-OHDA (Item No. 25330).2 It also inhibits monoamine oxidase B (MAO-B; Ki = 100 nM) and reduces MAO-B activity in brain mitochondrial preparations from wild-type and A2A-/- mice.3

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Jacobson, K.A., Nikodijević, O., Padgett, W.L., et al. 8-(3-Chlorostyryl)caffeine (CSC) is a selective A2-adenosine antagonist in vitro and in vivo. FEBS Lett. 323(1-2), 141-144 (1993).

    2. Song, L., Kong, M., Ma, Y., et al. Inhibitory effect of 8-(3-chlorostryryl) caffeine on levodopa-induced motor fluctuation is associated with intracellular signaling pathway in 6-OHDA-lesioned rats. Brain Res. 1276, 171-179 (2009).

    3. Chen, J.-F., Steyn, S., Staal, R., et al. 8-(3-Chlorostyryl)caffeine may attenuate MPTP neurotoxicity through dual actions of monoamine oxidase inhibition and A2A receptor antagonism. The Journal of Biological Chemisty 277(39), 36040-36044 (2002).