I7018

3-Isobutyl-1-methylxanthine

≥99%, Phosphodiesterase inhibitor

• 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: 247859
• EC Number: 249-259-3
• MDL number: MFCD00005584
• UNSPSC Code: 12352202
• PubChem Substance ID: 24896107
• NACRES: NA.77

Properties

• Product Name: 3-Isobutyl-1-methylxanthine, BioUltra, ≥99%
• product line: BioUltra
• Quality Level: 200
• Assay: ≥99%
• impurities: <0.005% Phosphorus (P)
• ign. residue: <0.1%
• mp: 200-201 °C (lit.)
• solubility: DMSO: soluble 1 M (with gentle warming)
• anion traces: sulfate (SO₄^2-): <0.05%
• cation traces: Al: <0.0005%; Ca: <0.005%; Cu: <0.0005%; Fe: <0.005%; K: <0.05%; Mg: <0.005%; NH₄⁺: <0.05%; Na: <0.005%; Pb: <0.001%; Zn: <0.0005%
• 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: rat ... Adora1(29290), Adora2a(25369)

Description

Application

3-Isobutyl-1-methylxanthine, an inhibitor of adenosine 3′,5′-cyclic monophosphate phosphodiesterase (cAMP PDE), has been used:

• for adipogenic differentiation[1]
• in tissue culture[2]
• 3T3-L1 preadipocyte differentiation([3]

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.

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.

Features and Benefits

• Trace element testing by ICP
• ICP testing for trace sulfur (as sulfate) and phosphorus (as phosphate) content
• Ion chromatography testing for trace ammonium content

Safety Information

• Storage Class Code: 11 - Combustible Solids
• WGK: WGK 3
• Flash Point(F): Not applicable
• Flash Point(C): Not applicable
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves