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I5879 Sigma

3-Isobutyl-1-methylxanthine

≥99% (HPLC), powder

Synonym: 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

  • CAS Number 28822-58-4

  • Empirical Formula (Hill Notation) C10H14N4O2

  • Molecular Weight 222.24

  •  Beilstein Registry Number 247859

  •  EC Number 249-259-3

  •  MDL number MFCD00005584

  •  PubChem Substance ID 24277680

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Properties

Related Categories Bioactives/Supplements, Cell Biology, Cell Signaling and Neuroscience, Cyclic Nucleotide Metabolism, Enzymes, Substrates, Inhibitors &, Modulators for Stem Cell Biology,
InChI Key   APIXJSLKIYYUKG-UHFFFAOYSA-N
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
Gene Information   human ... PRKAR1A(5573), PRKAR1AP(5574), PRKAR1B(5575), PRKAR2A(5576), PRKAR2B(5577)
rat ... Adora1(29290), Adora2a(25369)

Description

Packaging

1, 5 g in poly bottle

250 mg in poly tube

100 mg in poly bottle

Biochem/physiol Actions

Non-specific inhibitor of cAMP and cGMP phosphodiesterases. 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). Also serves as an adenosine receptor antagonist. Shown to inhibit ion channels in the neuromuscular junction, GH3 cells, and vascular smooth muscle cells. Induces calcium release from intracellular stores in sensory neurons.

Features and Benefits

This compound is also offered as part of Sigma′s Library of Pharmacologically Active Compounds (LOPAC®1280), a biologically annotated collection of high-quality, ready-to-screen compounds. Click here to learn more.

Legal Information

LOPAC is a registered trademark of Sigma-Aldrich Co. LLC

Safety & Documentation

Safety Information

Personal Protective Equipment 
RIDADR 
NONH for all modes of transport
WGK Germany 
3
RTECS 
ZD8500000

Frequently Asked Questions

Which document(s) contains shelf-life or expiration date information for a given product?
If available for a given product, the recommended re-test date or the expiration date can be found on the Certificate of Analysis.
How do I get lot-specific information or a Certificate of Analysis?
The lot specific COA document can be found by entering the lot number above under the "Documents" section.
How do I find price and availability?
There are several ways to find pricing and availability for our products.Once you log onto our website, you will find the price and availability displayed on the product detail page.You can contact any of our Customer Sales and Service offices to receive a quote. USA customers: 1-800-325-3010 orview local office numbers.
What is the expiration date of Product No. I5879, 3-Isobutyl-1-methylxanthine?
We do not assign an expiration date to this product.We will guarantee the quality of the product for one year from the time of shipment, providing all storage conditions are followed.
Is Product No. I5879, 3-Isobutyl-1-methylxanthine, appropriate for cell culture use?
Product No. I5879 is not a cell culture tested product. However, customers may wish to try this product in their cell culture applications.
What is the difference between 3-Isobutyl-1-methylxanthine Product I5879 and I7018?
Product No. I5879 is reagent grade. Product No. I7018, SigmaUltra grade, has been subjected to additional testing for trace metal impurities.
What is the Department of Transportation shipping information for this product?
Transportation information can be found in Section 14 of the product's (M)SDS.To access the shipping information for this material, use the link on the product detail page for the product.
My question is not addressed here, how can I contact Technical Service for assistance?
Ask a Scientist here.
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LC-MS Grade Solvents and Reagents
Protocols & Articles

Protocols

Polyene-lipids: A new tool to image lipids

Lars Kuerschner a , Christer S Ejsing a , Kim Ekroos b , Andrej Shevchenko a , Kurt I Anderson a , Christoph Thiele a
Keywords: Biochemistry, Capillary electrophoresis, Cell biology, Cell culture, Cell signaling, Chromatography, Detection methods, Detergents, Genetics, Magnetic resonance spectroscopy, Mass spectrometry, Metabolism, Metabolites, Microscopy, Molecular probes, Nuclear magnetic resonance spectroscopy, Phase transitions, Reversible addition-fragmentation chain transfer polymerizations, Scanning electron microscopy, Separation, Spectroscopy, Thin layer chromatography, Wittig Reaction

Peer-Reviewed Papers
15

References

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