1H-Purine-2,6-dione, 3,7-dihydro-1-methyl-3-(2-methylpropyl)-
3,7-dihydro-3-isobutyl-1-methyl-1H-purine-2,6-dione
CAS: 28822-58-4
Molecular Formula: C10H14N4O2
1H-Purine-2,6-dione, 3,7-dihydro-1-methyl-3-(2-methylpropyl)- - Names and Identifiers
| Name | 3,7-dihydro-3-isobutyl-1-methyl-1H-purine-2,6-dione |
| Synonyms | IMX Isobutylmethylxanthine Methylisobutylxanthine 3-isobutyl-1-methyl-xanthin 3-Isobutyl-1-methylanxthine 3,7-dihydro-3-isobutyl-1-methyl-1H-purine-2,6-dione 3-Isobutyl-1-methyl-3,7-dihydro-1H-purine-2,6-dione 3,7-dihydro-1-methyl-3-(2-methylpropyl)-1h-purine-6-dione 1H-Purine-2,6-dione, 3,7-dihydro-1-methyl-3-(2-methylpropyl)- |
| CAS | 28822-58-4 |
| EINECS | 249-259-3 |
| InChI | InChI=1/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 |
1H-Purine-2,6-dione, 3,7-dihydro-1-methyl-3-(2-methylpropyl)- - Physico-chemical Properties
| Molecular Formula | C10H14N4O2 |
| Molar Mass | 222.24 |
| Density | 1.2042 (rough estimate) |
| Melting Point | 200-201°C(lit.) |
| Boling Point | 363.42°C (rough estimate) |
| Flash Point | 223.3°C |
| Solubility | DMSO: 1M with gentle warming |
| Vapor Presure | 3.89E-08mmHg at 25°C |
| Appearance | Powder |
| Color | off-white |
| BRN | 247859 |
| pKa | 8.61±0.70(Predicted) |
| Storage Condition | -20°C |
| Stability | Stable for 2 years from date of purchase as supplied. Solutions in DMSO or ethanol may be stored at -20°C for up to 3 months. |
| Refractive Index | 1.6500 (estimate) |
| MDL | MFCD00005584 |
| Use | Non-specific inhibitors of cAMP and cGMP phosphodilipase. IBMX inhibits phosphodilipase, and the increase of cAMP activates PKA, which results in reduced proliferation, increased differentiation and induced apoptosis. IBMX inhibits the decrease of tryptamine (reduced mucus IC50: 1.3 μM from neuroendocrine epithelial cells) induced by phenylephrine. Also acts as an adenosine receptor antagonist. |
| In vitro study | At 100 μM, KMUP-1 (a xanthine derivative) and IBMX are the most effective at inducing tracheal relaxation; the magnitude of the relaxation responses induced by KMUP-1 and IBMX are not significantly different. IBMX (100 μM) activates renal outer medullary K + (ROMK) channels (n=6, P<0.05) and prevents further channel activation by ANG II (n=6, P=NS) or cGMP. Of note is that pretreatment of cortical collecting duct (CCDs) isolated from high-K + (HK)-fed rats with IBMX (100 μM) for 20 min leads to a significant increase in tubular cAMP content to 1.43±0.35 pg/mm tubule length (n=14) compare with that measured in vehicle-treated controls (0.61±0.13 pg/mm tubule length, n=12, P<0.05). |
| In vivo study | IBMX, a non-selective PDE inhibitor significantly decreases the liver glycogen storage (mg/g, IBMX 22±1.5 P<0.001). In comparison with the control group, IBMX and mc5 significantly increase plasma glucose (blood glucose, mg/dl, control=141±3, IBMX=210±17 P<0.001 and mc5=191±13 P<0.01) while other test compounds (mc1, mc6, MCPIP and Win 47203) do not produce significant effect (control=141±3, mc1 160±7, mc6 175±9, MCPIP 179±8 and Win 47203 116±2 P>0.05) also mc2 does not change plasma glucose (control=141±3 and mc2=145±5). IBMX has the highest efficacy on increasing plasma glucose. Treatments with IBMX and Apocynin significantly decrease cold-induced elevation of right ventricular (RV) systolic pressure (23.5±1.8 and 24.2±0.6 mmHg, respectively) although they do not decrease RV pressure to the warm control levels. IBMX or Apocynin significantly reduces medial layer thickness (19.0±0.9, and 16.9±0.8 μm, respectively) and increases lumen diameter (62.7±4.2, and 59.5±4.3 μm, respectively) of small PAs in cold-exposed rats. |
1H-Purine-2,6-dione, 3,7-dihydro-1-methyl-3-(2-methylpropyl)- - Risk and Safety
| Hazard Symbols | Xn - Harmful |
| Risk Codes | 22 - Harmful if swallowed |
| Safety Description | 24/25 - Avoid contact with skin and eyes. |
| WGK Germany | 3 |
| RTECS | ZD8500000 |
| HS Code | 29335990 |
1H-Purine-2,6-dione, 3,7-dihydro-1-methyl-3-(2-methylpropyl)- - Reference Information
| biological activity | IBMX (Isobutylmethylxanthine, 1-Methyl-3-Isobutylxanthine) is a non-specific phosphodiesterase (PDE) inhibitor. The IC50 values of PDE3, PDE4 and PDE5 are 6.5±1.2, 26.3±3.9 and 31.7±5.3 μM respectively. It can enhance intracellular cAMP level and is a adenosine (A1) receptor antagonist. |
| Target | Value |
| PDE3 () | 6.5 μM |
| PDE4 () | 26.3 μM |
| PDE5 () | 31.7 μM |
| use | cyclic nucleotide phosphodiesterase protein inhibitor. Non-specific inhibitors of cAMP and cGMP phosphodilipase. IBMX inhibits phosphodilipase, and the increase of cAMP activates PKA, which results in reduced proliferation, increased differentiation and induced apoptosis. IBMX inhibits the decrease of tryptamine (reduced mucus IC50: 1.3 μM from neuroendocrine epithelial cells) induced by phenylephrine. Also acts as an adenosine receptor antagonist. |
Last Update：2024-04-09 21:04:16
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