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Key Documents

C197

Sigma-Aldrich

8-(3-Chlorostyryl)caffeine

≥98% (HPLC), solid

Synonym(s):

1,3,7-Trimethyl-8-(3-chlorostyryl)xanthine, CSC

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About This Item

Empirical Formula (Hill Notation):
C16H15ClN4O2
CAS Number:
Molecular Weight:
330.77
MDL number:
UNSPSC Code:
12352200
PubChem Substance ID:
NACRES:
NA.77

Quality Level

Assay

≥98% (HPLC)

form

solid

color

white

solubility

DMSO: >5 mg/mL

storage temp.

−20°C

SMILES string

[H]\C(=C(\[H])c1nc2C(=O)N(C)C(=O)N(C)c2n1C)c3cccc(Cl)c3

InChI

1S/C16H15ClN4O2/c1-19-12(8-7-10-5-4-6-11(17)9-10)18-13-14(19)20(2)16(23)21(3)15(13)22/h4-9H,1-3H3/b8-7+

InChI key

MHYRUZOJQQLLQS-BQYQJAHWSA-N

Gene Information

Application

8-(3-Chlorostyryl)caffeine has been used as an adenosine A2A receptor antagonist:
  • to study its effects on levodopa (L-DOPA)-induced dopamine (DA) release in rat striatum
  • to study its effect on the nuclear factor κ-light-chain-enhancer of activated B cells (NF-κB) activity in macrophages
  • to determine its effects on human umbilical vein endothelial cells (HUVECs)

Biochem/physiol Actions

8-(3-Chlorostyryl)caffeine is a selective adenosine A2A receptor antagonist and monoamine oxidase B (MAO B) inhibitor.

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.

Caution

Photosensitive, store in the dark

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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