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Merck

I5879

3-Isobutyl-1-methylxanthine

≥99% (HPLC), cAMP and cGMP phosphodiesterases inhibitor, powder

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:
24277680
UNSPSC Code:
12352202
EC Number:
249-259-3
MDL number:
MFCD00005584
Beilstein/REAXYS Number:
247859

Product Name

3-Isobutyl-1-methylxanthine, ≥99% (HPLC), powder

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

SMILES string

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

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

Quality Level

200

Gene Information

human ... PRKAR1A(5573), PRKAR1AP(5574), PRKAR1B(5575), PRKAR2A(5576), PRKAR2B(5577)
rat ... Adora1(29290), Adora2a(25369)

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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

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.

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.

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

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Certificates of Analysis (COA)

Lot/Batch Number
STBF6061V
BCBS5838V
STBG0799V
BCBR4890V
STBB6785V

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  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.

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    The lot specific COA document can be found by entering the lot number above under the "Documents" section.

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  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. 

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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)
Skin pigmentation enhancers
Comprehensive Series in Photosciences, 3, 637-675 (2001)
Canine adipose-derived-mesenchymal stem cells do not lose stem features after a long-term cryopreservation
Martinello T, et al.
Research in Veterinary Science, 91(1), 18-24 (2011)
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)
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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