I5879

3-Isobutyl-1-methylxanthine

≥99% (HPLC), powder

• Synonym(s): 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, IBMX
• Empirical Formula (Hill Notation): C₁₀H₁₄N₄O₂
• CAS Number: 28822-58-4
• Molecular Weight: 222.24
• Beilstein/REAXYS Number: 247859
• EC Number: 249-259-3
• MDL number: MFCD00005584
• UNSPSC Code: 12352202
• PubChem Substance ID: 24277680
• NACRES: NA.77

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
• storage temp.: −20°C
• SMILES string: CC(C)CN1C(=O)N(C)C(=O)c2[nH]cnc12
• 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)
• InChI key: APIXJSLKIYYUKG-UHFFFAOYSA-N
• Gene Information: human ... PRKAR1A(5573) , PRKAR1AP(5574) , PRKAR1B(5575) , PRKAR2A(5576) , PRKAR2B(5577) ; rat ... Adora1(29290) , Adora2a(25369)

Description

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.

Application

3-Isobutyl-1-methylxanthine has been used:

• in the differentiation of mesenchymal stem cells (MSC)
• as a culture medium supplement for inducing adipogenic differentiation
• as a supplement in Krebs-Ringer buffer with HEPES (KRBH) solution for inducing glucose-stimulated insulin secretion (GSIS)
• in the characterization of adipose-derived mesenchymal stem cells
• in cyclic adenosine monophosphate (cAMP) assay
• in phosphodiesterase (PDE) inhibition

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.

Safety Information

• Storage Class: 11 - Combustible Solids
• wgk_germany: WGK 3
• flash_point_f: Not applicable
• flash_point_c: Not applicable
• ppe: dust mask type N95 (US), Eyeshields, Faceshields, Gloves