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858455

Sigma-Aldrich

3-Isobutyl-1-methylxanthine

99%

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
Beilstein/REAXYS Number:
247859
EC Number:
249-259-3
MDL number:
MFCD00005584
UNSPSC Code:
12352100

assay

99%

mp

200-201 °C (lit.)

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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Application

Potent inhibitor of cyclic nucleotide phosphodiesterase.

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.

replaced by

Product No.
Description
Pricing

Storage Class

13 - Non Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

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

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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X Pan et al.
Biochemical pharmacology, 48(4), 827-835 (1994-08-17)
The interaction between selective inhibitors of 3',5'-cyclic-nucleotide phosphodiesterase (PDE) III (cyclic GMP inhibited phosphodiesterase) and selective inhibitors of PDE IV (Ro 20-1724 inhibited phosphodiesterase) to attenuate fetal bovine serum-stimulated incorporation of [3H]thymidine into DNA and cell proliferation was studied in
D M Essayan et al.
Journal of immunology (Baltimore, Md. : 1950), 153(8), 3408-3416 (1994-10-15)
Cyclic nucleotide phosphodiesterase (PDE) enzymes are felt to play a role in the regulation of inflammatory responses through their effects on cAMP. In this study, we investigated the effects of nonselective and isozyme selective PDE inhibitors on the proliferative responses
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)
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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