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I7018

Sigma-Aldrich

3-Isobutyl-1-methylxanthine

BioUltra, ≥99%

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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
PubChem Substance ID:
24896107
NACRES:
NA.77

product line

BioUltra

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 (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

rat ... Adora1(29290) , Adora2a(25369)

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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(

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

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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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)
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)
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)
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
Ryan D Rose et al.
Theriogenology, 79(1), 142-148 (2012-10-30)
Physical removal of mammalian cumulus-oocyte complexes (COCs) from ovarian follicles results in spontaneous resumption of meiosis, largely because of a decrease in cAMP concentrations, causing asynchrony between cytoplasmic and nuclear maturation and decreased oocyte developmental competence. The aim of this
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