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

• ChemBase ID: 103456
• Molecular Formular: C13H12N4O2
• Molecular Mass: 256.25998
• Monoisotopic Mass: 256.09602564
• SMILES: Cn1c(=O)n(C)c2c([nH]c(n2)c2ccccc2)c1=O
• Canonical SMILES: Cn1c2nc([nH]c2c(=O)n(c1=O)C)c1ccccc1
• InChI: InChI=1S/C13H12N4O2/c1-16-11-9(12(18)17(2)13(16)19)14-10(15-11)8-6-4-3-5-7-8/h3-7H,1-2H3,(H,14,15)
• InChIKey: PJFMAVHETLRJHJ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1,3-dimethyl-8-phenyl-2,3,6,9-tetrahydro-1H-purine-2,6-dione; 1,3-dimethyl-8-phenyl-2,3,6,7-tetrahydro-1H-purine-2,6-dione
• IUPAC Traditional name: 1,3-dimethyl-8-phenyl-2,3,6,7-tetrahydro-1H-purine-2,6-dione; 8-phenyltheophylline
• Synonyms: 8-Phenyltheophylline; 1,3-Dimethyl-8-phenylxanthine; 8-PHENYLTHEOPHYLLINE; 8-Phenyltheophylline; 1,3-Dimethyl-8-phenylxanthine

Database IDs

• CAS Number: 961-45-5
• MDL Number: MFCD00005582
• Beilstein Number: 261704
• PubChem SID: 162090452; 24278626; 24853617
• PubChem CID: 1922
• CHEMBL: 62350
• Chemspider ID: 1846
• Wikipedia Title: 8-Phenyltheophylline

CALCULATED PROPERTIES

• Acid pKa: 7.1814876
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 1.2476053
• LogD (pH = 7.4): 0.911705
• Log P: 1.2554486
• Molar Refractivity: 80.0361 cm^3
• Polarizability: 26.261997 Å^3
• Polar Surface Area: 69.3 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: aqueous base: moderately soluble (Solutions should be stored at 4 °C.); ethanol: moderately soluble (Solutions should be stored at 4 °C.); H2O: slightly soluble
• Apperance: off-white to light yellow crystalline
• Melting Point: >300 °C(lit.)

Safety Information

• Storage Condition: 2-8°C
• RTECS: UO8445700
• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Pharmacology Properties

• Gene Information: human ... ADORA1(134), ADORA2B(136), ADORA3(140)rat ... Adora1(29290), Adora2a(25369), Adora2b(29316); human ... ADORA2B(136)rat ... Adora1(29290), Adora2a(25369), Adora2b(29316)
• Mechanism of Action: Antagonist of cyclic-AMP accumulation; Purine-antagonist

Product Information

• Purity: 98%
• Potency: 86 nM Ki for A1 receptors
• Empirical Formula (Hill Notation): C13H12N4O2

DETAILS

MP Biomedicals - 02151846

Crystalline
A potent antagonist of adenosine-mediated accumulation of cAMP in a human fibroblast cell line.

Sigma Aldrich - P2278

Biochem/physiol Actions
Selective A1 adenosine receptor antagonist.
Packaging
1 g in glass bottle
100 mg in glass bottle

Sigma Aldrich - 227161

Packaging
100 mg in glass bottle

REFERENCES

• Life Sci., 24: 2475 (1979).
• Aldrich Library of FT-IR Spectra, 1st edn., 1985, 2, 712A, (ir)
• Traube, W. et al., Ber., 1906, 39, 227, (derivs)
• Bergmann, F. et al., J.C.S., 1961, 4468, (synth)
• Taylor, E.C. et al., J.A.C.S., 1964, 86, 4721, (derivs)
• Goldner, H. et al., Annalen, 1966, 691, 142, (derivs)
• Smellie, F.W. et al., Life Sci., 1979, 24, 2475, (pharmacol)
• Oh, C.-H. et al., Arch. Pharm. (Weinheim, Ger.), 2001, 334, 345-350, (synth, pmr)