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:
24277680
NACRES: NA.77
Quality Level: 200
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)
General description
3-isobutyl-1-methylxanthine/IBMX is a non-selective,
non-specific inhibitor of cAMP and cGMP phosphodiesterases.[1] IBMX can
induce melanogenesis, and can be used as a positive control in melanogenesis
research.[2] 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)[3]
- as a
culture medium supplement for inducing adipogenic differentiation[4]
- as a
supplement in Krebs-Ringer buffer with HEPES (KRBH) solution for inducing
glucose-stimulated insulin secretion (GSIS)[5]
- in
the characterization of adipose-derived mesenchymal stem cells[6]
- in
cyclic adenosine monophosphate (cAMP) assay[7]
- in
phosphodiesterase (PDE) inhibition[8]
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.
