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

• ChemBase编号: 5583
• 分子式: C10H14N4O2
• 平均质量: 222.24376
• 单一同位素质量: 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

名称和登记号

名称

• IUPAC标准名: 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传统名: isobutylmethylxanthine; 3 isobutyl 1 methylxanthine; 3-isobutyl-1-methylxanthine; 1-methyl-3-(2-methylpropyl)-2,3,6,9-tetrahydro-1H-purine-2,6-dione
• 别名: 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; 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

登记号

• CAS号: 28822-58-4
• EC号: 249-259-3
• MDL号: MFCD00005584
• Beilstein号: 247859
• PubChem SID: 160969011; 24277680; 99444425; 24896107
• PubChem CID: 3758
• CHEBI ID: 34795
• CHEMBL: 275084
• Chemspider ID: 3627
• DrugBank ID: DB07954
• IUPHAR配体索引: 388
• KEGG ID: C13708
• 美国药典/FDA物质标识码: TBT296U68M
• 维基百科标题: IBMX

理论计算性质

JChem

• Acid pKa: 11.408139
• 质子受体: 3
• 质子供体: 1
• LogD (pH = 5.5): 0.43533114
• LogD (pH = 7.4): 0.43562138
• Log P: 0.4356642
• 摩尔折射率: 57.369 cm^3
• 极化性: 21.586395 Å^3
• 极化表面积: 69.3 Å^2
• 可自由旋转的化学键: 2
• 里宾斯基五规则: true

ALOGPS 2.1

• Log P: 0.84
• LOG S: -1.61
• 溶解度: 5.44e+00 g/l

分子性质

理化性质

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

安全信息

• 保存条件: 0°C; -20°C Freezer
• RTECS编号: ZD8500000
• 欧盟危险性物质标志: 有害性(Harmful) (Xn)
• 德国WGK号: 3
• 危险公开号: 22
• GHS危险品标识: GHS07
• GHS警示词: Warning
• GHS危险声明: H302
• 个人保护装置: dust mask type N95 (US), Eyeshields, Faceshields, Gloves
• 保存温度: -20°C

药理学性质

• 相关基因信息: human ... PRKAR1A(5573), PRKAR1AP(5574), PRKAR1B(5575), PRKAR2A(5576), PRKAR2B(5577)rat ... Adora1(29290), Adora2a(25369); rat ... Adora1(29290), Adora2a(25369)
• 生物活性机理: Phosphodiesterase inhibitor

产品相关信息

• 纯度: ≥98.0% (HPLC); ≥99%; ≥99% (HPLC); 99%
• 级别: purum
• 燃烧残渣: <0.1%
• 杂质: <0.005% Phosphorus (P)
• 痕量阳离子: 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%
• 痕量阴离子: sulfate (SO42-): <0.05%
• 应用领域: Antidepressant; Psychostimulant
• Empirical Formula (Hill Notation): C10H14N4O2

详细说明

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
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

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
环核苷酸磷酸二酯酶蛋白抑制剂2,3
包装
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.

参考文献

• 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)