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28822-58-4 molecular structure
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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 and InChIs

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

Cite this record

CBID:5583 http://www.chembase.cn/molecule-5583.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
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
CAS Number
28822-58-4
EC Number
249-259-3
MDL Number
MFCD00005584
Beilstein Number
247859
PubChem SID
160969011
24277680
99444425
24896107
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

CALCULATED PROPERTIES

JChem ALOGPS 2.1
Acid pKa 11.408139  H Acceptors
H Donor LogD (pH = 5.5) 0.43533114 
LogD (pH = 7.4) 0.43562138  Log P 0.4356642 
Molar Refractivity 57.369 cm3 Polarizability 21.586395 Å3
Polar Surface Area 69.3 Å2 Rotatable Bonds
Lipinski's Rule of Five true 
Log P 0.84  LOG S -1.61 
Solubility (Water) 5.44e+00 g/l 

PROPERTIES

PROPERTIES

Physical Property Safety Information Pharmacology Properties Product Information Bioassay(PubChem)
Solubility
Dichloromethane expand Show data source
DMSO: soluble1 M (with gentle warming) expand Show data source
ethanol: soluble10 mg/mL expand Show data source
Ether expand Show data source
Ethyl Acetate expand Show data source
Methanol expand Show data source
Soluble in ethanol, DMSO, and methanol expand Show data source
Apperance
White solid expand Show data source
White Solid expand Show data source
white to off-white powder expand Show data source
Melting Point
199-201 °C expand Show data source
200°C expand Show data source
200-201 °C(lit.) expand Show data source
200-201°C expand Show data source
201-203 °C expand Show data source
Storage Condition
0°C expand Show data source
-20°C Freezer expand Show data source
RTECS
ZD8500000 expand Show data source
European Hazard Symbols
Harmful Harmful (Xn) expand Show data source
MSDS Link
Download expand Show data source
Download expand Show data source
Download expand Show data source
Download expand Show data source
German water hazard class
3 expand Show data source
Risk Statements
22 expand Show data source
GHS Pictograms
GHS07 expand Show data source
GHS Signal Word
Warning expand Show data source
GHS Hazard statements
H302 expand Show data source
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Faceshields, Gloves expand Show data source
Storage Temperature
-20°C expand Show data source
Gene Information
human ... PRKAR1A(5573), PRKAR1AP(5574), PRKAR1B(5575), PRKAR2A(5576), PRKAR2B(5577)rat ... Adora1(29290), Adora2a(25369) expand Show data source
rat ... Adora1(29290), Adora2a(25369) expand Show data source
Mechanism of Action
Phosphodiesterase inhibitor expand Show data source
Purity
≥98.0% (HPLC) expand Show data source
≥99% expand Show data source
≥99% (HPLC) expand Show data source
99% expand Show data source
Grade
purum expand Show data source
Certificate of Analysis
Download expand Show data source
Download expand Show data source
Ignition Residue
<0.1% expand Show data source
Impurities
<0.005% Phosphorus (P) expand Show data source
Cation Traces
Al: <0.0005% expand Show data source
Ca: <0.005% expand Show data source
Cu: <0.0005% expand Show data source
Fe: <0.005% expand Show data source
K: <0.05% expand Show data source
Mg: <0.005% expand Show data source
Na: <0.005% expand Show data source
NH4+: <0.05% expand Show data source
Pb: <0.001% expand Show data source
Zn: <0.0005% expand Show data source
Antion Traces
sulfate (SO42-): <0.05% expand Show data source
Application(s)
Antidepressant expand Show data source
Psychostimulant expand Show data source
Empirical Formula (Hill Notation)
C10H14N4O2 expand Show data source

DETAILS

DETAILS

MP Biomedicals MP Biomedicals DrugBank DrugBank Wikipedia Wikipedia Sigma Aldrich Sigma Aldrich TRC TRC
MP Biomedicals - 02195262 external link
Inhibits cyclic-AMP phosphodiesterase.
DrugBank - DB07954 external link
Drug information: experimental
Sigma Aldrich - I7018 external link
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 external link
Frequently Asked Questions
Live Chat and Frequently Asked Questions are available for this Product.
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 external link
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 external link
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 external link
A nonspecific inhibitor of phosphodiesterases.

REFERENCES

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • 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)
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PATENTS

PATENTS

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INTERNET

INTERNET

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