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Merck

C101

8-Cyclopentyl-1,3-dipropylxanthine

A1 adenosine receptor antagonist, solid

Synonym(s):

1,3-Dipropyl-8-cyclopentylxanthine, DPCPX, PD 116,948

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About This Item

Empirical Formula (Hill Notation):
C16H24N4O2
CAS Number:
102146-07-6
Molecular Weight:
304.39
UNSPSC Code:
12352202
PubChem Substance ID:
24277697
NACRES:
NA.77
MDL number:
MFCD00055117

Product Name

8-Cyclopentyl-1,3-dipropylxanthine, solid

SMILES string

CCCN1C(=O)N(CCC)c2nc([nH]c2C1=O)C3CCCC3

InChI

1S/C16H24N4O2/c1-3-9-19-14-12(15(21)20(10-4-2)16(19)22)17-13(18-14)11-7-5-6-8-11/h11H,3-10H2,1-2H3,(H,17,18)

InChI key

FFBDFADSZUINTG-UHFFFAOYSA-N

form

solid

color

white

solubility

DMSO: >10 mg/mL
0.1 M NaOH: 2 mg/mL
ethanol: 4 mg/mL
H2O: insoluble

εmax

14,800 at 276 nm in ethanol

Quality Level

100

Gene Information

human ... ADORA1(134), ADORA2A(135), ADORA2B(136), ADORA3(140)
rat ... Adora1(29290), Adora2a(25369), Adora2b(29316), Adora3(25370)

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Application

8-Cyclopentyl-1,3-dipropylxanthine has been used as an adenosine receptor (A1AR) antagonist in macrophages and human umbilical vein endothelial cells (HUVECs). It has also been used as A1AR antagonist in MCF-7 breast cancer cell line to test its anti-cancer effect.

Biochem/physiol Actions

8-Cyclopentyl-1,3-dipropylxanthine (DPCPX) is a selective A1 adenosine receptor antagonist. DPCPX possesses anti-cancer functionality. It induces apoptosis in breast cancer cells and favors mRNA expression of caspases.

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.

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
0000500493
0000316642
0000316642
0000500493
0000072838

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Lindsay Silva et al.
Neurotoxicology and teratology, 58, 88-100 (2016-02-24)
Adolescents who use marijuana are more likely to exhibit anxiety, depression, and other mood disorders, including psychotic-like symptoms. Additionally, the age at onset of use and the stress history of the individual can affect responses to cannabis. To examine the
Hongjie Chen et al.
Experimental hematology, 37(5), 533-538 (2009-04-21)
The control of expression of tumor necrosis factor-alpha (TNF-alpha) impacts a variety of processes during a stress response. Macrophages are a major source of TNF-alpha, the level of which is known to be regulated by adenosine. Previous studies highlighted the
Jordi Bonaventura et al.
Nature communications, 10(1), 4627-4627 (2019-10-13)
Designer Receptors Exclusively Activated by Designer Drugs (DREADDs) are a popular chemogenetic technology for manipulation of neuronal activity in uninstrumented awake animals with potential for human applications as well. The prototypical DREADD agonist clozapine N-oxide (CNO) lacks brain entry and
Mariachiara Zuccarini et al.
Purinergic signalling, 13(4), 429-442 (2017-06-16)
Epithelial to mesenchymal transition (EMT) occurs during embryogenesis or under pathological conditions such as hypoxia, injury, chronic inflammation, or tissue fibrosis. In renal tubular epithelial cells (MDCK), TGF-β1 induces EMT by reducing or increasing epithelial or mesenchymal marker expression, respectively.
Daniela Patinha et al.
American journal of physiology. Renal physiology, 304(5), F614-F622 (2013-01-04)
Increased angiotensin II (ANG II) or adenosine can potentiate each other in the regulation of renal hemodynamics and tubular function. Diabetes is characterized by hyperfiltration, yet the roles of ANG II and adenosine receptors for controlling baseline renal blood flow
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