| Identification | Back Directory | [Name]
8-(3-CHLOROSTYRYL) CAFFEINE A2A ADENOSIN E RECEPTO | [CAS]
147700-11-6 | [Synonyms]
1,3,7-Trimethyl-8-(3-chlorostyryl)xanthine, CSC
8-(3-CHLOROSTYRYL) CAFFEINE A2A ADENOSIN E RECEPTO
8-[2-(3-Chloro-phenyl)-vinyl]-1,3,7-trimethyl-3,7-dihydro-purine-2,6-dione
(E)-8-[2-(3-Chlorophenyl)ethenyl]-3,7-dihydro-1,3,7-trimethyl-1H-purine-2,6-dione
1H-Purine-2,6-dione,8-[(1E)-2-(3-chlorophenyl)ethenyl]-3,7-dihydro-1,3,7-triMethyl- | [Molecular Formula]
C16H15ClN4O2 | [MDL Number]
MFCD00210188 | [MOL File]
147700-11-6.mol | [Molecular Weight]
330.77 |
| Chemical Properties | Back Directory | [Melting point ]
205 °C | [Boiling point ]
559.4±60.0 °C(Predicted) | [density ]
1.36±0.1 g/cm3(Predicted) | [storage temp. ]
−20°C | [solubility ]
DMSO: >5mg/mL | [form ]
solid | [pka]
0.12±0.70(Predicted) | [color ]
white |
| Hazard Information | Back Directory | [Description]
8-(3-Chlorostyryl)caffeine (CSC) is an adenosine A2 receptor antagonist (Ki = 54 nM). 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 in a rat model of Parkinson’s disease induced by 6-OHDA . 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. | [Uses]
8-(3-Chlorostyryl)caffeine is a selective Adenosine A2A-R and MAO-B inhibitor. | [Definition]
ChEBI: 8-(3-chlorostyryl)caffeine is caffeine substituted at its 8-position by an (E)-3-chlorostyryl group. It has a role as an adenosine A2A receptor antagonist and an EC 1.4.3.4 (monoamine oxidase) inhibitor. It is a trimethylxanthine and a member of monochlorobenzenes. It is functionally related to a caffeine. | [IC 50]
A2AR; MAO-B: 70 nM (Ki) | [storage]
Store at -20°C | [References]
[1] KENNETH A. JACOBSON. 8-(3-Chlorostyryl)caffeine (CSC) is a selective A2-adenosine antagonist in vitro and in vivo[J]. FEBS Letters, 1993, 323 1: Pages 141-144. DOI: 10.1016/0014-5793(93)81466-d
[2] LU SONG . Inhibitory effect of 8-(3-chlorostryryl) caffeine on levodopa-induced motor fluctuation is associated with intracellular signaling pathway in 6-OHDA-lesioned rats[J]. Brain Research, 2009, 1276: Pages 171-179. DOI: 10.1016/j.brainres.2009.04.028
[3] JIANG-FAN CHEN. 8-(3-Chlorostyryl)caffeine May Attenuate MPTP Neurotoxicity through Dual Actions of Monoamine Oxidase Inhibition and A2A Receptor Antagonism*[J]. The Journal of Biological Chemistry, 2002, 56 1: 36040-36044. DOI: 10.1074/jbc.m206830200 |
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