| Identification | More | [Name]
3-ISOBUTYL-1-METHYLXANTHINE | [CAS]
28822-58-4 | [Synonyms]
1-METHYL-3-ISOBUTYL XANTHINE
3-ISOBUTYL-1-METHYL-2,6(1H,3H)-PURINEDIONE
3-ISOBUTYL-1-METHYLXANTHINE
3-ISOBUTYL-I-METHYLXANTHINE
IBMX
MIX
1H-Purine-2,6-dione, 3,7-dihydro-1-methyl-3-(2-methylpropyl)-
3,7-dihydro-1-methyl-3-(2-methylpropyl)-1h-purine-6-dione
3-Isobutyl-1-methyl-3,7-dihydro-1H-purine-2,6-dione
3-Isobutyl-1-methylanxthine
3-isobutyl-1-methyl-xanthin
IMX
Isobutylmethylxanthine
Methylisobutylxanthine
SC 2964
Xanthine, 3-Isobutyl-1-methyl-
3,7-Dihydro-1-methyl-3-(2-methylpropyl)-1H-purine-2,6-dione
3,7-dihydro-3-isobutyl-1-methyl-1H-purine-2,6-dione
3-ISOBUTYL-1-METHYLXANTHINE SIGMAULTRA
Isobutyl-1-methylxanthine | [EINECS(EC#)]
249-259-3 | [Molecular Formula]
C10H14N4O2 | [MDL Number]
MFCD00005584 | [Molecular Weight]
222.24 | [MOL File]
28822-58-4.mol |
| Chemical Properties | Back Directory | [Appearance]
White Needles with Yellow Cast | [Melting point ]
200-201 °C(lit.)
| [Boiling point ]
363.42°C (rough estimate) | [density ]
1.2042 (rough estimate) | [refractive index ]
1.6500 (estimate) | [storage temp. ]
−20°C
| [solubility ]
DMSO: 1 M with gentle warming
| [form ]
powder
| [pka]
8.61±0.70(Predicted) | [color ]
off-white
| [Usage]
A nonspecific inhibitor of phosphodiesterases | [BRN ]
247859 | [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. | [InChIKey]
APIXJSLKIYYUKG-UHFFFAOYSA-N | [CAS DataBase Reference]
28822-58-4(CAS DataBase Reference) |
| Safety Data | Back Directory | [Hazard Codes ]
Xn | [Risk Statements ]
R22:Harmful if swallowed. | [Safety Statements ]
S24/25:Avoid contact with skin and eyes . | [WGK Germany ]
3
| [RTECS ]
ZD8500000
| [HS Code ]
29335990 |
| Hazard Information | Back Directory | [Description]
IBMX (28822-58-4) is a pan-specific inhibitor of phosphodiesterases (IC50=2-50 μM). Inhibition of PDEs leads to increased concentration of intracellular cAMP which activates PKA.2?IBMX does not inhibit PDE8 or PDE9.3?Weak adenosine receptor antagonist.4 | [Chemical Properties]
White Needles with Yellow Cast | [Uses]
3-Isobutyl-1-methylxanthine is used in inhibition of phenylephrine-induced release of 5-hydroxytryptamine from neuroendocrine epithelial cells of the airway mucosa (IC50 = 1.3 uM). Also inhibits ion channels in the neuromuscular junction, GH3 cells, and vascular smooth muscle cells. Inhibits the growth of carcinoma cells both in vivo and in vitro in mice. | [Uses]
A nonspecific inhibitor of phosphodiesterases | [Uses]
phosphodiesterase inhibitor | [Definition]
ChEBI: 3-isobutyl-1-methyl-9H-xanthine is a 3-isobutyl-1-methylxanthine. It is functionally related to a 9H-xanthine. It is a tautomer of a 3-isobutyl-1-methyl-7H-xanthine. | [General Description]
3-isobutyl-1-methylxanthine/IBMX is a non-selective, non-specific inhibitor of cAMP and cGMP phosphodiesterases. IBMX can induce melanogenesis, and can be used as a positive control in melanogenesis research. In oocyte research, IBMX assists in maintaining the germinal vesicle (GV) arrest of prophase I oocytes. | [Biological Activity]
Phosphodiesterase inhibitor (IC 50 values are 13, 18, 19, 32 and 50 μ M for PDE4, PDE3, PDE1, PDE5 and PDE2 respectively). Suppresses α -adrenoceptor-mediated 5-HT release from neuroendocrine epithelial cells (IC 50 = 1.3 μ M). | [Biochem/physiol Actions]
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). IBMX also serves as an adenosine receptor antagonist. IBMX has been shown to inhibit ion channels in the neuromuscular junction, GH3 cells, and vascular smooth muscle cells. IBMX induces calcium release from intracellular stores in sensory neurons. | [storage]
+4°C | [Purification Methods]
Recrystallise it from aqueous EtOH. [Beilstein 26 | [References]
1) Beavo et al. (1970), Effects of xanthine derivatives on lipolysis and on adenosine 3′,5′-monophosphate phosphodiesterase activity; Mol. Pharmacol., 6 597
2) Tomes et al. (1993), Isobutylmethylxanthine and other classical cyclic nucleotide phosphodiesterase inhibitors affect cAMP-dependent protein kinase activity; Cell Signal., 5 615
3) Soderling et al. (2000), Regulation of cAMP and cGMP signaling: new phosphodiesterases and new functions; Curr. Opin. Cell Biol., 12 174
4) Daly et al. (1987), Adenosine receptors: development of selective agonists and antagonists; Prog. Clin. Biol. Res., 230 41 |
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