I5879

Sigma-Aldrich

3-Isobutyl-1-methylxanthine

≥99% (HPLC), powder

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

Quality Level

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

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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General description

3-isobutyl-1-methylxanthine/IBMX is a non-selective, non-specific inhibitor of cAMP and cGMP phosphodiesterases. IBMX can induce melanogenesis, and can be used as a positive control in melanogenesis research. In oocyte research, IBMX assists in maintaining the germinal vesicle (GV) arrest of prophase I oocytes.

Application

3-Isobutyl-1-methylxanthine has been used:
  • in the differentiation of mesenchymal stem cells (MSC)
  • as a culture medium supplement for inducing adipogenic differentiation
  • as a supplement in Krebs-Ringer buffer with HEPES (KRBH) solution for inducing glucose-stimulated insulin secretion (GSIS)
  • in the characterization of adipose-derived mesenchymal stem cells
  • in cyclic adenosine monophosphate (cAMP) assay
  • in phosphodiesterase (PDE) inhibition

Packaging

1, 5 g in poly bottle
100 mg in poly bottle
250 mg in poly tube

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

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

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

  1. 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.

  2. 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.

  3. 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 or view local office numbers.

  4. 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. 

  5. 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.

  6. 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.

  7. 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. 

  8. My question is not addressed here, how can I contact Technical Service for assistance?

    Ask a Scientist here.

A conserved aromatic lock for the tryptophan rotameric switch in TM-VI of seven-transmembrane receptors
Holst B, et al.
The Journal of Biological Chemistry, 285(6), 3973-3985 (2010)
ZebraBeat: a flexible platform for the analysis of the cardiac rate in zebrafish embryos
De L, et al.
Scientific reports, 4, 4898-4898 (2014)
Skin pigmentation enhancers
Comprehensive Series in Photosciences, 3, 637-675 (2001)
Crystal structures of phosphodiesterases 4 and 5 in complex with inhibitor 3-isobutyl-1-methylxanthine suggest a conformation determinant of inhibitor selectivity
Huai Q, et al.
The Journal of Biological Sciences, 279(13), 13095-13101 (2004)
Adult bone marrow is a rich source of human mesenchymal `stem?cells but umbilical cord and mobilized adult blood are not
Wexler SA, et al.
British Journal of Haematology, 121(2), 368-374 (2003)

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