1,7-dimethyl-2,3,6,7-tetrahydro-1H-purine-2,6-dione

• ChemBase ID: 128826
• Molecular Formular: C7H8N4O2
• Molecular Mass: 180.16402
• Monoisotopic Mass: 180.06472552
• SMILES: O=c1[nH]c2ncn(c2c(=O)n1C)C
• Canonical SMILES: Cn1cnc2c1c(=O)n(c(=O)[nH]2)C
• InChI: InChI=1S/C7H8N4O2/c1-10-3-8-5-4(10)6(12)11(2)7(13)9-5/h3H,1-2H3,(H,9,13)
• InChIKey: QUNWUDVFRNGTCO-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1,7-dimethyl-2,3,6,7-tetrahydro-1H-purine-2,6-dione
• IUPAC Traditional name: paraxanthine
• Synonyms: 1,7-Dimethyl-1H-purine-2,6-dione; 2,6-Dihydroxy-1,7-dimethylpurine; 1,7-Dimethylxanthine; paraxanthine; 1 ,7-Dimethylxanthine; Paraxanthine; 1,7-Dimethylxanthine; 3,7-Dihydro-1,7-dimethyl-1H-purine-2,6-dione

Database IDs

• CAS Number: 611-59-6
• EC Number: 210-271-9
• MDL Number: MFCD00005727
• Beilstein Number: 197907
• PubChem SID: 24277678; 162223130
• PubChem CID: 4687
• CHEBI ID: 25858
• CHEMBL: 1158
• Chemspider ID: 4525
• Unique Ingredient Identifier: Q3565Y41V7
• Wikipedia Title: Paraxanthine

CALCULATED PROPERTIES

• Acid pKa: 10.761287
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 0.2402859
• LogD (pH = 7.4): 0.24010879
• Log P: 0.24028835
• Molar Refractivity: 46.7153 cm^3
• Polarizability: 16.055227 Å^3
• Polar Surface Area: 67.23 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: 0.1 M NaOH: soluble2 mg/mL; 0.1N Sodium Hydroxide (2 mg/ml); Ethanol (0.6 mg/ml); ethanol: soluble0.6 mg/mL; H2O: soluble1 mg/mL; Water (1 mg/ml)
• Apperance: Off-White to Pale Yellow Solid; white solid
• Melting Point: 294-296 °C; 294-296 °C(lit.); 297-299°C; 351 - 352°C

Safety Information

• Storage Condition: -20°C Freezer
• Storage Warning: Store tightly sealed at RT
• RTECS: RV9380000
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 22
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302
• 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)

Product Information

• Purity: ~98%; ≥97.0% (HPLC)
• Suitability: suitable for 1694 per US EPA
• Empirical Formula (Hill Notation): C7H8N4O2

DETAILS

Sigma Aldrich - D5385

Biochem/physiol Actions
Adenosine receptor ligand; major metabolite of caffeine
包装
100, 500 mg in poly bottle

Sigma Aldrich - 41761

Application
Ligand for the adenosine receptor

Toronto Research Chemicals - P192500

An adenosine receptor ligand and a major metabolite of caffeine.

REFERENCES

• Proc. Natl. Acad. Sci. USA 78, 3260 (1981)
• Cell Mol. Neurobiol., 3, 69 (1981)
• Eur. J. Pharmacol., 179, 295 (1990)