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Merck
모든 사진(1)

문서

C197

Sigma-Aldrich

8-(3-Chlorostyryl)caffeine

≥98% (HPLC), solid

동의어(들):

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

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About This Item

실험식(Hill 표기법):
C16H15ClN4O2
CAS Number:
Molecular Weight:
330.77
MDL number:
UNSPSC 코드:
12352200
PubChem Substance ID:
NACRES:
NA.77

분석

≥98% (HPLC)

형태

solid

색상

white

solubility

DMSO: >5 mg/mL

저장 온도

−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

유전자 정보

애플리케이션

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)

생화학적/생리학적 작용

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

특징 및 장점

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.

주의사항

Photosensitive, store in the dark

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point (°F)

Not applicable

Flash Point (°C)

Not applicable

개인 보호 장비

Eyeshields, Gloves, type N95 (US)


시험 성적서(COA)

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문서 라이브러리 방문

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
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
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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