Skip to Content
Merck

C197

8-(3-Chlorostyryl)caffeine

≥98% (HPLC), solid

Synonym(s):

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

Sign In to View Organizational & Contract Pricing.

Select a Size

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

Key Documents

View All Documentation
Technical Service
Need help? Our team of experienced scientists is here for you.
Let Us Assist
Technical Service
Need help? Our team of experienced scientists is here for you.
Let Us Assist

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 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.

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)

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

Choose from one of the most recent versions:

Certificates of Analysis (COA)

Lot/Batch Number
111M4719V
0000035693
127K47094
127K47093
127K47092

Don't see the Right Version?

If you require a particular version, you can look up a specific certificate by the Lot or Batch number.

Search for a COA

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

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
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
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
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
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
View All Related Papers

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service