I5879
 |  |  |
 |
Image
Useful Links & Tools
- MSDS
- Specification Sheet
- Certificate of Analysis
- Certificate of Origin
- I5879 - Product Information Sheet (56 KB)
- Celltransmissions 20(1) (708 KB )
- FT-IR Raman
- Bulk Quote
I5879
Sigma
3-Isobutyl-1-methylxanthine
≥99% (HPLC), powder
| Synonym: | 1-Methyl-3-isobutylxanthine, 3-Isobutyl-1-methyl-2,6(1H,3H)-purinedione, IBMX, 3,7-Dihydro-1-methyl-3-(2-methylpropyl)-1H-purine-2,6-dione |
| CAS Number: | 28822-58-4 |
| Linear Formula: | C10H14N4O2 |
| Molecular Weight: | 222.24 |
| Beilstein Registry Number: | 247859 |
| EC Number: | 249-259-3 |
| MDL number: | MFCD00005584 |
| PubChem Substance ID: | 24277680 |
Description
| Frequently Asked Questions | Live Chat and Frequently Asked Questions are available for this Product. |
| 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. |
Properties
| assay | ≥99% (HPLC) |
| form | powder |
| color | white to off-white |
| mp | 200-201 °C(lit.) |
| solubility | DMSO: 1 M with gentle warming |
| ethanol: 10 mg/mL | |
| Gene Information | human ... PRKAR1A(5573), PRKAR1AP(5574), PRKAR1B(5575), PRKAR2A(5576), PRKAR2B(5577) |
| rat ... Adora1(29290), Adora2a(25369) | |
| storage temp. | −20°C |
Safety
| Personal Protective Equipment | dust mask type N95 (US), Eyeshields, Faceshields, Gloves |
| Hazard Codes | Xn |
| Risk Statements | 22 |
| WGK Germany | 3 |
| RTECS | ZD8500000 |
References
| reference | Shafer, S.H., et al., Reduced DNA synthesis and cell viability in small cell lung carcinoma by treatment with cyclic AMP phosphodiesterase inhibitors. Biochem. Pharmacol. 56, 1229-1236, (1998) |
| Chen, T.C., et al., Up-regulation of the cAMP/PKA pathway inhibits proliferation, induces differentiation, and leads to apoptosis in malignant gliomas. Lab. Invest. 78, 165-174, (1998) | |
| Elks, M.L., and Manganiello, V.C., A role for soluble cAMP phosphodiesterases in differentiation of 3T3-L1adipocytes. J. Cell Physiol. 124, 191-198, (1985) | |
| Freitag, A., et al., Phosphodiesterase inhibitors suppress α2-adrenoceptor-mediated 5-hydroxytryptamine release from tracheae of newborn rabbits. Eur. J. Pharmacol. 354, 67-71, (1998) | |
| McKinley, J.B., et al., The interaction of adenosine analogues with cAMP-generating and cAMP-independent positive inotropic agents in rabbit left atrium. Naunyn Schmiedebergs Arch. Pharmacol. 342, 605-612, (1990) | |
| Fearon, I.M., et al., Inhibition of recombinant human cardiac L-type Ca2+ channel α1C subunits by 3-isobutyl-1-methylxanthine. Eur. J. Pharmacol. 342, 353-358, (1998) | |
| Beilstein | Beil. 26,IV,2350 |
| FT-IR 1 (2), 711:C / FT-IR 2 (3), 3670:A / IR-Spectra (2), 1120:G / IR-Spectra (3), 1288:B / NMR-Reference 2 (2), 586:D / RegBook 1 (2), 2467:K / Sigma FT-IR 1 (1), 1002:C / Structure Index 1, 390:E:4 |
