1,3,9-trimethyl-2,3,6,9-tetrahydro-1H-purine-2,6-dione

• ChemBase ID: 133320
• Molecular Formular: C8H10N4O2
• Molecular Mass: 194.1906
• Monoisotopic Mass: 194.08037558
• SMILES: Cn1cnc2c1n(c(=O)n(c2=O)C)C
• Canonical SMILES: O=c1n(C)c2n(C)cnc2c(=O)n1C
• InChI: InChI=1S/C8H10N4O2/c1-10-4-9-5-6(10)11(2)8(14)12(3)7(5)13/h4H,1-3H3
• InChIKey: LPHGQDQBBGAPDZ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1,3,9-trimethyl-2,3,6,9-tetrahydro-1H-purine-2,6-dione
• IUPAC Traditional name: 1,3,9-trimethylpurine-2,6-dione
• Synonyms: 2,6-Dihydroxy-1,3,9-trimethylpurine; Isocaffeine; 1,3,9-Trimethylxanthine

Database IDs

• CAS Number: 519-32-4
• EC Number: 208-267-7
• MDL Number: MFCD00022834
• Beilstein Number: 196140
• PubChem SID: 24900197; 162227597
• PubChem CID: 1326

CALCULATED PROPERTIES

• H Acceptors: 3
• H Donor: 0
• LogD (pH = 5.5): -0.58521354
• LogD (pH = 7.4): -0.58496606
• Log P: -0.5849629
• Molar Refractivity: 48.5215 cm^3
• Polarizability: 17.869284 Å^3
• Polar Surface Area: 58.44 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: H2O: >20 mg/mL
• Apperance: solid

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: room temp

Product Information

• Purity: ≥98% (HPLC)

DETAILS

Sigma Aldrich - T4146

Biochem/physiol Actions
1,3,9-Trimethylxanthine is an adenosine receptor antagonist.
Application
1,3,9-Trimethylxanthine (Isocaffeine) may be used to study the mechanism of inositol-trisphosphate (Ins-P3) induced calcium release. 1,3,9-Trimethylxanthine may be used as an internal standard for measuring metabolites of caffeine in urine and other fluids by HPLC or capillary electrophoresis. 1,3,9-Trimethylxanthine may be used in studies on the binding of caffeine analogues to adenosine receptors.