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C197

Sigma-Aldrich

8-(3-Chlorostyryl)caffeine

≥98% (HPLC), solid

Synonym(e):

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

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About This Item

Empirische Formel (Hill-System):
C16H15ClN4O2
CAS-Nummer:
147700-11-6
Molekulargewicht:
330.77
MDL-Nummer:
MFCD00210188
UNSPSC-Code:
12352200
PubChem Substanz-ID:
24277703
NACRES:
NA.77

Assay

≥98% (HPLC)

Form

solid

Farbe

white

Löslichkeit

DMSO: >5 mg/mL

Lagertemp.

−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+

InChIKey

MHYRUZOJQQLLQS-BQYQJAHWSA-N

Angaben zum Gen

human ... ADORA2A(135)
mouse ... Maob(109731)
rat ... Adora1(29290) , Adora2a(25369)

Anwendung

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. Wirkung

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

Leistungsmerkmale und Vorteile

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.

Vorsicht

Photosensitive, store in the dark

Lagerklassenschlüssel

11 - Combustible Solids

WGK

WGK 3

Flammpunkt (°F)

Not applicable

Flammpunkt (°C)

Not applicable

Persönliche Schutzausrüstung

Eyeshields, Gloves, type N95 (US)

Analysenzertifikate (COA)

Suchen Sie nach Analysenzertifikate (COA), indem Sie die Lot-/Chargennummer des Produkts eingeben. Lot- und Chargennummern sind auf dem Produktetikett hinter den Wörtern ‘Lot’ oder ‘Batch’ (Lot oder Charge) zu finden.

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Rangel L Silva et al.
Toxicology and applied pharmacology, 368, 63-71 (2019-02-24)
Cannabidiol (CBD) is a natural compound with psychoactive therapeutic properties well described. Conversely, the immunological effects of CBD are still poorly explored. In this study, the potential anti-inflammatory effects and underlying mechanisms of CBD and its analog Dimethyl-Heptyl-Cannabidiol (DMH-CBD) were
K A Jacobson et al.
Journal of medicinal chemistry, 36(10), 1333-1342 (1993-05-14)
A series of substituted 8-styryl derivatives of 1,3,7-alkylxanthines was synthesized as potential A2-selective adenosine receptor antagonists, and the potency at rat brain A1- and A2-receptors was studied in radioligand binding experiments. At the xanthine 7-position, only small hydrophobic substituents were
K A Jacobson et al.
FEBS letters, 323(1-2), 141-144 (1993-05-24)
An adenosine antagonist, 8-(3-chlorostyryl)caffeine (CSC), was shown previously to be 520-fold selective for A2a-adenosine receptors in radioligand binding assays in the rat brain. In reversing agonist effects on adenylate cyclase, CSC was 22-fold selective for A2a receptors in rat phenochromocytoma
Krystyna Gołembiowska et al.
Brain research, 998(2), 208-217 (2004-01-31)
In the present study, we investigated effects of the new selective adenosine A2A receptor antagonist 8-(3-chlorostyryl)caffeine (CSC) on L-DOPA-induced dopamine (DA) release in the striatum of intact and reserpine-treated rats. CSC given in a pharmacologically effective dose of 5 mg/kg
Eduardo P Amaral et al.
The Journal of infectious diseases, 219(6), 964-974 (2018-10-12)
Tuberculous pneumonia, necrotic granulomatous lesions, and bacterial dissemination characterize severe forms of mycobacterial infection. To evaluate the pulmonary CD4+ T-cell response during severe tuberculosis, C57BL/6 mice were infected with approximately 100 bacilli of 3 hypervirulent mycobacterial isolates (Mycobacterium tuberculosis strain
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