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

• ChemBase ID: 1894
• Molecular Formular: C5H4N4O2
• Molecular Mass: 152.11086
• Monoisotopic Mass: 152.03342539
• SMILES: c12c([nH]c(=O)[nH]c1=O)nc[nH]2
• Canonical SMILES: O=c1[nH]c(=O)c2c([nH]1)nc[nH]2
• InChI: InChI=1S/C5H4N4O2/c10-4-2-3(7-1-6-2)8-5(11)9-4/h1H,(H3,6,7,8,9,10,11)
• InChIKey: LRFVTYWOQMYALW-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2,3,6,9-tetrahydro-1H-purine-2,6-dione; 2,3,6,7-tetrahydro-1H-purine-2,6-dione
• IUPAC Traditional name: Xan; xanthine
• Synonyms: 1H-Purine-2,6(3H,7H)-dione; Xanthine; 2,6-Dihydroxypurine; 3,9-Dihydro-1H-purine-2,6-dione; 1H,3H,7H-Xanthine; 1H,3H,9H-Xanthine; 1H-Purine-2,6-diol; 2,6-Dioxo-1,2,3,6-tetrahydropurine; 2,6-Dioxopurine; 3,9-Dihydropurine-2,6-dione; 9H-Purine-2,6(1H,3H)-dione; Isoxanthine; NSC 14664; Pseudoxanthine; Purine-2,6(1H,3H)-dione; Xan; Xanthic oxide; Xanthin; Xanthine; 2,6-二羟基嘌呤; 黄嘌呤

Database IDs

• CAS Number: 69-89-6
• EC Number: 200-718-6
• MDL Number: MFCD00078453
• Beilstein Number: 8733
• Merck Index: 1410059
• PubChem SID: 24902156; 160965349; 46507575; 24902144; 24902122
• PubChem CID: 1188

CALCULATED PROPERTIES

JChem

• Acid pKa: 7.954238
• H Acceptors: 3
• H Donor: 3
• LogD (pH = 5.5): -0.20843261
• LogD (pH = 7.4): -0.30188677
• Log P: -0.2070638
• Molar Refractivity: 36.9219 cm^3
• Polarizability: 12.519744 Å^3
• Polar Surface Area: 86.88 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: -0.65
• LOG S: -1.49
• Solubility (Water): 4.91e+00 g/l

PROPERTIES

Physical Property

• Solubility: 0.069 mg/mL at 16 oC [MERCK INDEX (1996)]; 1 M NaOH: soluble0.1 M, clear, colorless to light yellow; DSMO; NaOH: freely soluble; NH4OH: freely soluble
• Apperance: Off-White Solid
• Melting Point: >300°C; Decomposes without melting
• Hydrophobicity(logP): -0.73 [HANSCH,C ET AL. (1995)]

Safety Information

• Storage Condition: Refrigerator; Room Temperature (15-30°C)
• Storage Warning: IRRITANT
• RTECS: ZD7700000
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36-43
• Safety Statements: 36/37
• TSCA Listed: false; 是
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H317-H319
• GHS Precautionary statements: P280-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Faceshields, Gloves

Product Information

• Purity: ≥99%; ≥99.0% (HPLC); ≥99.5% (HPLC); 95+%; 98%; 99%; 99-100%
• Grade: puriss.
• Ignition Residue: ≤0.1%
• Impurities: ≤0.0005% Phosphorus (P); ≤0.1% Insoluble matter
• Cation Traces: Al: ≤0.0005%; Ca: ≤0.0005%; Cu: ≤0.0005%; Fe: ≤0.0005%; K: ≤0.005%; Mg: ≤0.0005%; Na: ≤0.005%; NH4+: ≤0.05%; Pb: ≤0.001%; Zn: ≤0.0005%
• Antion Traces: sulfate (SO42-): <0.05%
• Purified By: recrystallization
• Quality Level: ELITE
• Empirical Formula (Hill Notation): C5H4N4O2
• Classification: Derivatives & analogs of Natural Compounds

DETAILS

MP Biomedicals - 02103290

Crystalline
Purity: 99-100%

DrugBank - DB02134

• Drug Groups: experimental
• Description: A purine base found in most body tissues and fluids, certain plants, and some urinary calculi. It is an intermediate in the degradation of adenosine monophosphate to uric acid, being formed by oxidation of hypoxanthine. The methylated xanthine compounds caffeine, theobromine, and theophylline and their derivatives are used in medicine for their bronchodilator effects. (Dorland, 28th ed)
• External Links: Wikipedia

Toronto Research Chemicals - X499950

Found in animal organs, yeast, patatoes, coffee beans, tea. This drug can be used to relax and widen certain breathing passages of the lungs. It is also found that a large number of derivatives have adenoside receptor antagonist properties.

REFERENCES

• Mueller, C. et. al: Handbook Exp. Pharmacol. 200,151(2011)