I7018

Sigma-Aldrich

3-Isobutyl-1-methylxanthine

BioUltra, ≥99%

Synonym(s):
3-Isobutyl-1-methyl-2,6(1H,3H)-purinedione, IBMX, 1-Methyl-3-isobutylxanthine, 3,7-Dihydro-1-methyl-3-(2-methylpropyl)-1H-purine-2,6-dione
Empirical Formula (Hill Notation):
C10H14N4O2
CAS Number:
Molecular Weight:
222.24
Beilstein/REAXYS Number:
247859
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.77

product line

BioUltra

Quality Level

assay

≥99%

impurities

<0.005% Phosphorus (P)

ign. residue

<0.1%

mp

200-201 °C (lit.)

solubility

DMSO: soluble 1 M (with gentle warning)

anion traces

sulfate (SO42-): <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

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Related Categories

Application

3-Isobutyl-1-methylxanthine, an inhibitor of adenosine 3′,5′-cyclic monophosphate phosphodiesterase (cAMP PDE), has been used:
  • for adipogenic differentiation
  • in tissue culture
  • 3T3-L1 preadipocyte differentiation(

Packaging

1 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.

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

storage_class_code

11 - Combustible Solids

WGK Germany

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

Certificate of Origin

Distinct roles of the phosphatidate phosphatases lipin 1 and 2 during adipogenesis and lipid droplet biogenesis in 3T3-L1 cells
Sembongi H, et al.
The Journal of biological chemistry, jbc-M113 (2013)
Preferential apelin-13 production by the proprotein convertase PCSK3 is implicated in obesity
Shin K, et al.
FEBS Open Bio, 3(1), 328-333 (2013)
Uniaxial mechanical strain modulates the differentiation of neural crest stem cells into smooth muscle lineage on micropatterned surfaces
Li X, et al.
PLoS ONE, 6(10), e26029-e26029 (2011)
The next generation of phosphodiesterase inhibitors: structural clues to ligand and substrate selectivity of phosphodiesterases.
David T Manallack et al.
Journal of medicinal chemistry, 48(10), 3449-3462 (2005-05-13)
Masayoshi Higuchi et al.
Stem cells and development, 22(6), 878-888 (2012-10-03)
Both reactive oxygen species (ROS) and Forkhead box O (FOXO) family transcription factors are involved in the regulation of adipogenic differentiation of preadipocytes and stem cells. While FOXO has a pivotal role in maintaining cellular redox homeostasis, the interactions between...

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