8-(methoxymethyl)-1-methyl-3-(2-methylpropyl)-2,3,6,7-tetrahydro-1H-purine-2,6-dione

• ChemBase ID: 105166
• Molecular Formular: C12H18N4O3
• Molecular Mass: 266.29632
• Monoisotopic Mass: 266.13789046
• SMILES: COCc1nc2c([nH]1)c(=O)n(C)c(=O)n2CC(C)C
• Canonical SMILES: COCc1[nH]c2c(n1)n(CC(C)C)c(=O)n(c2=O)C
• InChI: InChI=1S/C12H18N4O3/c1-7(2)5-16-10-9(11(17)15(3)12(16)18)13-8(14-10)6-19-4/h7H,5-6H2,1-4H3,(H,13,14)
• InChIKey: NBLBCGUCPBXKOV-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 8-(methoxymethyl)-1-methyl-3-(2-methylpropyl)-2,3,6,7-tetrahydro-1H-purine-2,6-dione; 8-(methoxymethyl)-1-methyl-3-(2-methylpropyl)-2,3,6,9-tetrahydro-1H-purine-2,6-dione
• IUPAC Traditional name: 8-(methoxymethyl)-1-methyl-3-(2-methylpropyl)-7H-purine-2,6-dione; 8-(methoxymethyl)-1-methyl-3-(2-methylpropyl)-9H-purine-2,6-dione
• Synonyms: 8-Methoxymethyl-IBMX; 8-METHOXYMETHYL-1-METHYL-3-(2-METHYLPROPYL)XANTHINE; 8-Methoxymethyl-3-isobutyl-1-methylxanthine; 3,7-Dihydro-8-(methoxymethyl)-1-methyl-3-(2-methylpropyl)-1H-purine-2,6-dione; 8-Methoxymethyl-3-isobutyl-1-methylxanthine; 8-Methoxymethyl-1-methyl-3-(2-methylpropyl) Xanthine

Database IDs

• CAS Number: 78033-08-6
• MDL Number: MFCD00211081
• PubChem SID: 24278541; 162105862
• PubChem CID: 155806

CALCULATED PROPERTIES

• Log P: 0.38460737
• Molar Refractivity: 68.2631 cm^3
• Polarizability: 25.976109 Å^3
• Polar Surface Area: 78.53 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true
• Acid pKa: 10.371393
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): 0.3845691
• LogD (pH = 7.4): 0.38419983

PROPERTIES

Physical Property

• Solubility: DMSO - 2mg in 0.5ml @ 25°C; Ethanol - 2mg in 0.4 ml - clear and colorless.; ethanol: soluble10 mg/mL
• Apperance: White Solid
• Melting Point: 189-190°C

Safety Information

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

Pharmacology Properties

• Gene Information: human ... PDE1A(5136), PDE1B(5153)

Product Information

• Purity: ≥98%; 98%
• Empirical Formula (Hill Notation): C12H18N4O3

DETAILS

MP Biomedicals - 02158955

Purity: 98%
Specifically inhibits Ca^2+ -calmodulin-dependent phosphodiesterase.

Sigma Aldrich - M2547

Biochem/physiol Actions
Selective inhibitor of Ca2+-calmodulin-dependent phosphodiesterase I (PDE1).

Toronto Research Chemicals - M264500

A specific inhibitor of calmodulin-sensitive cyclic GMP phosphodiesterase.

REFERENCES

• Wells, J.N. and Miller, J.R., Methods Enzymol. , 159 : 489 (1988).
• Ahn, H.S., et al., Biochem. Pharmacol. , 38 : 3331 (1989).
• Ahlstroem, M., Cell. Mol. Biol. Lett., 10, 305 (2005)
• Marte, A., et al.: J. Neurosci. Res., 86, 3338 (2005)