1-methyl-3-(2-methylpropyl)-2,3,6,9-tetrahydro-1H-purine-2,6-dione

• ChemBase ID: 5583
• Molecular Formular: C10H14N4O2
• Molecular Mass: 222.24376
• Monoisotopic Mass: 222.11167571
• SMILES: [nH]1cnc2c1n(c(=O)n(c2=O)C)CC(C)C
• Canonical SMILES: CC(Cn1c(=O)n(C)c(=O)c2c1[nH]cn2)C
• InChI: InChI=1S/C10H14N4O2/c1-6(2)4-14-8-7(11-5-12-8)9(15)13(3)10(14)16/h5-6H,4H2,1-3H3,(H,11,12)
• InChIKey: APIXJSLKIYYUKG-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-methyl-3-(2-methylpropyl)-2,3,6,9-tetrahydro-1H-purine-2,6-dione; 1-methyl-3-(2-methylpropyl)-2,3,6,7-tetrahydro-1H-purine-2,6-dione
• IUPAC Traditional name: isobutylmethylxanthine; 3 isobutyl 1 methylxanthine; 3-isobutyl-1-methylxanthine; 1-methyl-3-(2-methylpropyl)-2,3,6,9-tetrahydro-1H-purine-2,6-dione
• Synonyms: 3-Isobutyl-1-methylxanthine; 1-Methyl-3-isobutylxanthine; 3,7-Dihydro-1-methyl-3-(2-methylpropyl)-1H-purine-2,6-dione; 3-Isobutyl-1-methyl-2,6(1H,3H)-purinedione; 3-ISOBUTYL-1-METHYLXANTHINE; 3-Isobutyl-1-methylxanthine; IBMX; IBMX; 3,9-Dihydro-1-methyl-3-(2-methylpropyl)-1H-purine-2,6-dione; IMX; Isobutylmethylxanthine; Methylisobutylxanthine; NSC 165960; SC 2964; SC-2964; 1-甲基-3-异丁基黄嘌呤; 3,7-二氢-1-甲基-3-(2-甲基丙基)-1H-嘌呤-2,6-二酮; 3-异丁基-1-甲基-2,6(1H,3H)-嘌呤二酮; 3-异丁基-1-甲基黄嘌呤

Database IDs

• CAS Number: 28822-58-4
• EC Number: 249-259-3
• MDL Number: MFCD00005584
• Beilstein Number: 247859
• PubChem SID: 160969011; 24277680; 24896107; 99444425
• PubChem CID: 3758
• CHEBI ID: 34795
• CHEMBL: 275084
• Chemspider ID: 3627
• DrugBank ID: DB07954
• IUPHAR ligand ID: 388
• KEGG ID: C13708
• Unique Ingredient Identifier: TBT296U68M
• Wikipedia Title: IBMX

CALCULATED PROPERTIES

JChem

• Acid pKa: 11.408139
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 0.43533114
• LogD (pH = 7.4): 0.43562138
• Log P: 0.4356642
• Molar Refractivity: 57.369 cm^3
• Polarizability: 21.586395 Å^3
• Polar Surface Area: 69.3 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 0.84
• LOG S: -1.61
• Solubility (Water): 5.44e+00 g/l

PROPERTIES

Physical Property

• Solubility: Dichloromethane; DMSO: soluble1 M (with gentle warming); ethanol: soluble10 mg/mL; Ether; Ethyl Acetate; Methanol; Soluble in ethanol, DMSO, and methanol
• Apperance: White solid; White Solid; white to off-white powder
• Melting Point: 199-201 °C; 200°C; 200-201 °C(lit.); 200-201°C; 201-203 °C

Safety Information

• Storage Condition: 0°C; -20°C Freezer
• RTECS: ZD8500000
• 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, Faceshields, Gloves
• Storage Temperature: -20°C

Pharmacology Properties

• Gene Information: human ... PRKAR1A(5573), PRKAR1AP(5574), PRKAR1B(5575), PRKAR2A(5576), PRKAR2B(5577)rat ... Adora1(29290), Adora2a(25369); rat ... Adora1(29290), Adora2a(25369)
• Mechanism of Action: Phosphodiesterase inhibitor

Product Information

• Purity: ≥98.0% (HPLC); ≥99%; ≥99% (HPLC); 99%
• Grade: purum
• Ignition Residue: <0.1%
• Impurities: <0.005% Phosphorus (P)
• Cation Traces: Al: <0.0005%; Ca: <0.005%; Cu: <0.0005%; Fe: <0.005%; K: <0.05%; Mg: <0.005%; Na: <0.005%; NH4+: <0.05%; Pb: <0.001%; Zn: <0.0005%
• Antion Traces: sulfate (SO42-): <0.05%
• Application(s): Antidepressant; Psychostimulant
• Empirical Formula (Hill Notation): C10H14N4O2

DETAILS

MP Biomedicals - 02195262

Inhibits cyclic-AMP phosphodiesterase.

DrugBank - DB07954

Drug information: experimental

Sigma Aldrich - I7018

Biochem/physiol Actions
Non-specific inhibitor of cAMP and cGMP phosphodiesterases. The increase in cAMP level as a result of phosphodiesterase inhibition by IBMX activates PKA leading to decreased proliferation, increased differentiation, and induction of apoptosis. IBMX inhibits phenylephrine-induced release of 5-hydroxytryptamine from neuroendocrine epithelial cells of the airway mucosa (IC50: 1.3 μM). Also serves as an adenosine receptor antagonist. Shown to inhibit ion channels in the neuromuscular junction, GH3 cells, and vascular smooth muscle cells. Induces calcium release from intracellular stores in sensory neurons.1

Sigma Aldrich - I5879

Frequently Asked Questions
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包装
1, 5 g in poly bottle
250 mg in poly tube
100 mg in poly bottle
Biochem/physiol Actions
Non-specific inhibitor of cAMP and cGMP phosphodiesterases. The increase in cAMP level as a result of phosphodiesterase inhibition by IBMX activates PKA leading to decreased proliferation, increased differentiation, and induction of apoptosis. IBMX inhibits phenylephrine-induced release of 5-hydroxytryptamine from neuroendocrine epithelial cells of the airway mucosa (IC50: 1.3 μM). Also serves as an adenosine receptor antagonist. Shown to inhibit ion channels in the neuromuscular junction, GH3 cells, and vascular smooth muscle cells. Induces calcium release from intracellular stores in sensory neurons.1

Sigma Aldrich - 58620

Other Notes
Raises intracellular cyclic AMP levels2; Produces partial inhibition of cAMP-phosphodiesterase3
Biochem/physiol Actions
Non-specific inhibitor of cAMP and cGMP phosphodiesterases. The increase in cAMP level as a result of phosphodiesterase inhibition by IBMX activates PKA leading to decreased proliferation, increased differentiation, and induction of apoptosis. IBMX inhibits phenylephrine-induced release of 5-hydroxytryptamine from neuroendocrine epithelial cells of the airway mucosa (IC50: 1.3 μM). Also serves as an adenosine receptor antagonist. Shown to inhibit ion channels in the neuromuscular junction, GH3 cells, and vascular smooth muscle cells. Induces calcium release from intracellular stores in sensory neurons.1

Sigma Aldrich - 858455

Application
Potent inhibitor of cyclic nucleotide phosphodiesterase.2,3
Packaging
1 g in glass bottle
100 mg in glass bottle
Biochem/physiol Actions
Non-specific inhibitor of cAMP and cGMP phosphodiesterases. The increase in cAMP level as a result of phosphodiesterase inhibition by IBMX activates PKA leading to decreased proliferation, increased differentiation, and induction of apoptosis. IBMX inhibits phenylephrine-induced release of 5-hydroxytryptamine from neuroendocrine epithelial cells of the airway mucosa (IC50: 1.3 μM). Also serves as an adenosine receptor antagonist. Shown to inhibit ion channels in the neuromuscular junction, GH3 cells, and vascular smooth muscle cells. Induces calcium release from intracellular stores in sensory neurons.1

Toronto Research Chemicals - I785000

A nonspecific inhibitor of phosphodiesterases.

REFERENCES

• Beavo, J.A., et al., Molec. Pharmacol., 6: 597, (1970).
• Montague, W. and Cook, J.R., Biochem. J., 122: 115, (1971).
• Beavo., J.A., et al.: Mol. Pharmacol., 6, 597 (1970)
• Scamps, F., et al.: Eur. J. Pharmacol., 224, 119 (1993)