C197

8-(3-Chlorostyryl)caffeine

Name: 8-(3-Chlorostyryl)caffeine
Brand: SIGMA

≥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:

147700-11-6

Molecular Weight:

330.77

NACRES:

NA.77

PubChem Substance ID:

24277703

UNSPSC Code:

12352200

MDL number:

MFCD00210188

Product Name

8-(3-Chlorostyryl)caffeine, ≥98% (HPLC), solid

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+

SMILES string

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

InChI key

MHYRUZOJQQLLQS-BQYQJAHWSA-N

assay

≥98% (HPLC)

form

solid

color

white

solubility

DMSO: >5 mg/mL

storage temp.

−20°C

Quality Level

100

Gene Information

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

Application

8-(3-Chlorostyryl)caffeine has been used as an adenosine A_2A 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 A_2A receptor antagonist and monoamine oxidase B (MAO B) inhibitor.

Disclaimer

Photosensitive, store in the dark

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.

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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DMH-CBD, a cannabidiol analog with reduced cytotoxicity, inhibits TNF production by targeting NF-kB activity dependent on A2A receptor.

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

Structure-activity relationships of 8-styrylxanthines as A2-selective adenosine antagonists.

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

8-(3-Chlorostyryl)caffeine (CSC) is a selective A2-adenosine antagonist in vitro and in vivo.

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

Effect of the adenosine A2A receptor antagonist 8-(3-chlorostyryl)caffeine on L-DOPA biotransformation in rat striatum.

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

Effect of adenosine A(2A) receptor antagonists and L-DOPA on hydroxyl radical, glutamate and dopamine in the striatum of 6-OHDA-treated rats.

Krystyna Gołembiowska et al.

Neurotoxicity research, 21(2), 222-230 (2011-08-11)

A(2A) adenosine receptor antagonists have been proposed as a new therapy of PD. Since oxidative stress plays an important role in the pathogenesis of PD, we studied the effect of the selective A(2A) adenosine receptor antagonists 8-(-3-chlorostyryl)caffeine (CSC) and 4-(2-[7-amino-2-(2-furyl)[1,2,4]triazolo[2,3-a][1,3,5]triazin-5-ylamino]ethyl)phenol

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