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8-(3-CHLOROSTYRYL) CAFFEINE A2A ADENOSIN E RECEPTO

CAS No.
147700-11-6
Chemical Name:
8-(3-CHLOROSTYRYL) CAFFEINE A2A ADENOSIN E RECEPTO
Synonyms
(E)-8-(3-Chlorostyryl)caffeine;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-
CBNumber:
CB9972690
Molecular Formula:
C16H15ClN4O2
Molecular Weight:
330.77
MDL Number:
MFCD00210188
MOL File:
147700-11-6.mol
Last updated:2023-06-30 15:45:59

8-(3-CHLOROSTYRYL) CAFFEINE A2A ADENOSIN E RECEPTO Properties

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

SAFETY

Risk and Safety Statements

WGK Germany  3

8-(3-CHLOROSTYRYL) CAFFEINE A2A ADENOSIN E RECEPTO Chemical Properties,Uses,Production

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.

storage

Store at -20°C

5440-00-6
147700-11-6
Synthesis of 8-(3-CHLOROSTYRYL) CAFFEINE A2A ADENOSIN E RECEPTO from 5,6-Diamino-1,3-dimethyluracil hydrate

8-(3-CHLOROSTYRYL) CAFFEINE A2A ADENOSIN E RECEPTO Preparation Products And Raw materials

Raw materials

Preparation Products

8-(3-CHLOROSTYRYL) CAFFEINE A2A ADENOSIN E RECEPTO 1,3,7-Trimethyl-8-(3-chlorostyryl)xanthine, CSC 1H-Purine-2,6-dione,8-[(1E)-2-(3-chlorophenyl)ethenyl]-3,7-dihydro-1,3,7-triMethyl- 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 (E)-8-(3-Chlorostyryl)caffeine 147700-11-6