Merck
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I5879

Sigma-Aldrich

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:
Molecular Weight:
222.24
Beilstein:
247859
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.77

Quality Level

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

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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

Packaging

100 mg in poly bottle
250 mg in poly tube
1, 5 g in poly bottle

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 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

Certificate of Analysis

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Certificate of Origin

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