8-cyclopentyl-1,3-dipropyl-2,3,6,7-tetrahydro-1H-purine-2,6-dione

• ChemBase ID: 92978
• Molecular Formular: C16H24N4O2
• Molecular Mass: 304.38736
• Monoisotopic Mass: 304.18992603
• SMILES: [nH]1c2c(nc1C1CCCC1)n(c(=O)n(c2=O)CCC)CCC
• Canonical SMILES: CCCn1c2nc([nH]c2c(=O)n(c1=O)CCC)C1CCCC1
• InChI: 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)
• InChIKey: FFBDFADSZUINTG-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 8-cyclopentyl-1,3-dipropyl-2,3,6,7-tetrahydro-1H-purine-2,6-dione
• IUPAC Traditional name: dipropylcyclopentylxanthine; 8-cyclopentyl-1,3-dipropyl-7H-purine-2,6-dione
• Synonyms: 1,3-Dipropyl-8-cyclopentylxanthine; PD 116,948; 8-Cyclopentyl-1,3-dipropylxanthine; 8-Cyclopentyl-3,9-dihydro-1,3-dipropyl-1H-purine-2,6-dione; DPCPX, PD 116,948; 8-Cyclopentyl-1,3-dipropylxanthine; DPCPX; 8-Cyclopentyl-3,7-dihydro-1,3-dipropyl-1H-purine-2,6-dione; DPCPX, 1,3-Dipropyl-8-cyclopentylxanthine; 8-CYCLOPENTYL-1,3-DIPROPYLXANTHINE; 8-Cyclopentyl-1,3-dipropyl-1H-purine-2,6(3H,7H)-dione

Database IDs

• CAS Number: 102146-07-6
• MDL Number: MFCD00055117
• PubChem SID: 162079676; 24277697
• PubChem CID: 1329

CALCULATED PROPERTIES

• Acid pKa: 8.012483
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 2.780168
• LogD (pH = 7.4): 2.69929
• Log P: 2.7813373
• Molar Refractivity: 84.5216 cm^3
• Polarizability: 31.777079 Å^3
• Polar Surface Area: 69.3 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: 0.1 M NaOH: soluble2 mg/mL; 0.1N Sodium Hydroxide (2 mg/ml); DMSO (3.6 mg/ml); DMSO: >10 mg/mL; Ethanol (4 mg/ml); ethanol: soluble4 mg/mL; H2O: insoluble
• Apperance: white solid; White Solid
• Melting Point: 191-194°C; 191-194°C
• Absorption Wavelength: εmax/276 nm, ethanol 14,800

Safety Information

• Storage Condition: -20°C Freezer; Room Temperature (15-30°C)
• Storage Warning: Irritant/Store at -20°C
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-36
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

Pharmacology Properties

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

Product Information

• Purity: 97%

DETAILS

MP Biomedicals - 02153745

A1 adenosine receptor antagonist.

Apollo Scientific Ltd - OR9885T

A potent & selective A1-adenosine receptor antagonist, with a Ki of 0.46 nM for A1 receptors in rat whole-brain membranes.

Sigma Aldrich - C101

Biochem/physiol Actions
Selective A1 adenosine receptor antagonist.

Toronto Research Chemicals - C988500

DPCPX is a potent and very selective A1-adenosine receptor antagonist, with a Ki of 0.46 nM for A1 receptors in rat whole-brain membranes. Its 740-fold A1-selectivity is the highest reported for an adenosine antagonist.

REFERENCES

• Gessi, S., et al.: Mol. Pharmacol., 67, 2137 (2005)
• Minor, T.R., et al.: Behav. Neurosci., 122, 1236 (2005)
• Gracia, E., et al.: J. Neurochem., 107, 161 (2005)
• Gessi, S., et al.: Biochem. Pharmacol., 75, 562 (2005)