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C197

8-(3-Chlorostyryl)caffeine

≥98% (HPLC), solid

Synonym(s):

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

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Pack SizeSKUAvailabilityPrice
25 mg

Available to ship TODAYfromMILWAUKEE

$339.00

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

$339.00

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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)

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[1]
  • to study its effect on the nuclear factor κ-light-chain-enhancer of activated B cells (NF-κB) activity in macrophages[2]
  • to determine its effects on human umbilical vein endothelial cells (HUVECs)[3]

Biochem/physiol Actions

8-(3-Chlorostyryl)caffeine is a selective adenosine A2A receptor antagonist[1] and monoamine oxidase B (MAO B) inhibitor.[4]

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.

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This Item
205548D054C240
8-(3-Chlorostyryl)caffeine ≥98% (HPLC), solid

Sigma-Aldrich

C197

8-(3-Chlorostyryl)caffeine

Caffeine Trimethylated xanthine that acts as a potent central nervous system stimulant.

Sigma-Aldrich

205548

Caffeine

R(+)-SCH-23390 hydrochloride ≥98% (HPLC), solid

Sigma-Aldrich

D054

R(+)-SCH-23390 hydrochloride

8-(4-Chlorophenylthio)-guanosine 3′,5′-cyclic monophosphorothioate, Rp Isomer triethylammonium salt ≥98% (HPLC), solid

Sigma-Aldrich

C240

8-(4-Chlorophenylthio)-guanosine 3′,5′-cyclic monophosphorothioate, Rp Isomer triethylammonium salt

form

solid

form

solid

form

solid

form

solid

assay

≥98% (HPLC)

assay

≥99% (HPLC)

assay

≥98% (HPLC)

assay

≥98% (HPLC)

Quality Level

100

Quality Level

100

Quality Level

100

Quality Level

100

storage temp.

−20°C

storage temp.

10-30°C

storage temp.

-

storage temp.

−20°C

solubility

DMSO: >5 mg/mL

solubility

chloroform: 50 mg/mL

solubility

H2O: >5 mg/mL

solubility

H2O: 5 mg/mL

color

white

color

white

color

white

color

white

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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Certificates of Analysis (COA)

Lot/Batch Number
0000535682
0000531494
0000535682
0000531494
111M4719V

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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.
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
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Global Trade Item Number

SKUGTIN
C197-100MG04061832081472
C197-25MG04061832081489

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