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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

Assay:

≥98% (HPLC)

Form:

solid

Quality level:

100

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Properties

Quality Level

100

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

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

Description

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.

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.

Disclaimer

Photosensitive, store in the dark

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

C197-BULK: + C197-25MG: + C197-VAR: + C197-100MG:

jan

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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.