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Merck

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

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About This Item

Empirical Formula (Hill Notation):
C10H14N4O2
CAS Number:
28822-58-4
Molecular Weight:
222.24
NACRES:
NA.77
PubChem Substance ID:
24896107
UNSPSC Code:
12352202
EC Number:
249-259-3
MDL number:
MFCD00005584
Beilstein/REAXYS Number:
247859

Key Documents

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Product Name

3-Isobutyl-1-methylxanthine, BioUltra, ≥99%

InChI key

APIXJSLKIYYUKG-UHFFFAOYSA-N

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)

SMILES string

CC(C)CN1C(=O)N(C)C(=O)c2[nH]cnc12

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

Quality Level

200

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.
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

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Faceshields, Gloves

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

I7018-VAR: + I7018-250MG: + I7018-1G: + I7018-100MG: + I7018-BULK:

jan

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Certificates of Analysis (COA)

Lot/Batch Number
STBK3891
STBF2497V
STBF0977V
STBD6775V
STBD1971V

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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)
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
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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