8-cyclopentyl-1,3-dimethyl-2,3,6,9-tetrahydro-1H-purine-2,6-dione

• ChemBase ID: 103973
• Molecular Formular: C12H16N4O2
• Molecular Mass: 248.28104
• Monoisotopic Mass: 248.12732577
• SMILES: Cn1c(=O)n(C)c2c([nH]c(n2)C2CCCC2)c1=O
• Canonical SMILES: Cn1c2nc([nH]c2c(=O)n(c1=O)C)C1CCCC1
• InChI: InChI=1S/C12H16N4O2/c1-15-10-8(11(17)16(2)12(15)18)13-9(14-10)7-5-3-4-6-7/h7H,3-6H2,1-2H3,(H,13,14)
• InChIKey: SCVHFRLUNIOSGI-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 8-cyclopentyl-1,3-dimethyl-2,3,6,9-tetrahydro-1H-purine-2,6-dione; 8-cyclopentyl-1,3-dimethyl-2,3,6,7-tetrahydro-1H-purine-2,6-dione
• IUPAC Traditional name: 8-cyclopentyl-1,3-dimethyl-9H-purine-2,6-dione; 8-cyclopentyl-1,3-dimethyl-7H-purine-2,6-dione
• Synonyms: 8-Cyclopentyl-3,9-dihydro-1,3-dimethyl-1H-purine-2,6-dione; CPT, NSC 101806; CPT; 8-Cyclopentyl-1,3-dimethylxanthine; 8-Cyclopentyltheophylline; 8-CYCLOPENTYL-1,3-DIMETHYLXANTHINE

Database IDs

• CAS Number: 35873-49-5
• MDL Number: MFCD00055116
• PubChem SID: 24277730; 162091036
• PubChem CID: 1917
• CHEMBL: 106265
• Chemspider ID: 1843
• Wikipedia Title: 8-Cyclopentyl-1,3-dimethylxanthine

CALCULATED PROPERTIES

• Acid pKa: 8.043211
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 1.021587
• LogD (pH = 7.4): 0.94562656
• Log P: 1.0226766
• Molar Refractivity: 65.9764 cm^3
• Polarizability: 24.453636 Å^3
• Polar Surface Area: 69.3 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: 0.1 M NaOH: soluble; 0.1N Sodium Hydroxide; 45% (w/v) aq 2-hydroxypropyl-β-cyclodextrin: soluble0.77 mg/mL; DMSO; DMSO: ~16 mg/mL at 60 °C; H2O: slightly soluble <0.28 mg/mL; Water (<0.28 mg/ml)
• Apperance: white to off-white powder; White to Off-White Solid
• Melting Point: 250-252°C; 250-252°C

Safety Information

• Storage Condition: -20°C Freezer; Room Temperature (15-30°C)
• RTECS: XH5093600
• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Pharmacology Properties

• Legal Status: Uncontrolled
• Gene Information: human ... ADORA1(134)

Product Information

• Purity: ≥98% (HPLC)

DETAILS

MP Biomedicals - 02153746

A1 adenosine receptor antagonist.

Sigma Aldrich - C102

Biochem/physiol Actions
Selective A1 adenosine receptor antagonist.

Toronto Research Chemicals - C988490

A selective A1 adenosine receptor antagonist. Binding activity in rat brain membranes: Ki = 10.9 nM (A1 receptor); Ki = 1440 nM (A2 receptor).

REFERENCES

• Klaasse, E., et al.: Eur. J. Pharmacol., 499, 91 (2004)
• Romanelli, L., et al.: Neurotoxicol., 26, 829 (2004)
• Rezvani, M.E., et al.: Can. J. Physiol. Pharmacol., 85, 606 (2004)