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C101

Sigma-Aldrich

8-Cyclopentyl-1,3-dipropylxanthine

solid

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Synonym(s):
1,3-Dipropyl-8-cyclopentylxanthine, DPCPX, PD 116,948
Empirical Formula (Hill Notation):
C16H24N4O2
CAS Number:
Molecular Weight:
304.39
MDL number:
PubChem Substance ID:
NACRES:
NA.77

form

solid

Quality Level

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

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

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This Item
M2547D5385C102
8-Cyclopentyl-1,3-dipropylxanthine solid

C101

8-Cyclopentyl-1,3-dipropylxanthine

1,7-Dimethylxanthine ~98%, solid

D5385

1,7-Dimethylxanthine

8-Cyclopentyl-1,3-dimethylxanthine ≥98% (HPLC), powder

C102

8-Cyclopentyl-1,3-dimethylxanthine

Quality Level

100

Quality Level

-

Quality Level

200

Quality Level

-

solubility

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

solubility

ethanol: 10 mg/mL

solubility

ethanol: 0.6 mg/mL, H2O: 1 mg/mL, 0.1 M NaOH: 2 mg/mL

solubility

H2O: slightly soluble <0.28 mg/mL, 45% (w/v) aq 2-hydroxypropyl-β-cyclodextrin: 0.77 mg/mL, DMSO: ~16 mg/mL at 60 °C, 0.1 M NaOH: soluble

color

white

color

-

color

white

color

white to off-white

εmax

14,800 at 276 nm in ethanol

εmax

-

εmax

-

εmax

-

Gene Information

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

Gene Information

human ... PDE1A(5136), PDE1B(5153)

Gene Information

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

Gene Information

human ... ADORA1(134)

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

signalword

Warning

Hazard Classifications

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

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves


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