This product is not a sterile preparation. Stock solutions may be filter sterilized. Please see the link below to review additional information available in the product datasheet:
https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/product/documents/110/425/i5879pis-ms.pdf
I5879
3-Isobutyl-1-methylxanthine
≥99% (HPLC), cAMP and cGMP phosphodiesterases inhibitor, powder
3-Isobutyl-1-methylxanthine
1 of 1 reviewers received a sample product or took part in a promotion
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:
Molecular Weight:
222.24
NACRES:
NA.77
PubChem Substance ID:
UNSPSC Code:
12352202
EC Number:
249-259-3
MDL number:
Beilstein/REAXYS Number:
247859
Pricing and availability is not currently available.
Product Name
3-Isobutyl-1-methylxanthine, ≥99% (HPLC), powder
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
Gene Information
human ... PRKAR1A(5573), PRKAR1AP(5574), PRKAR1B(5575), PRKAR2A(5576), PRKAR2B(5577)
rat ... Adora1(29290), Adora2a(25369)
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
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.
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This Item | |||
|---|---|---|---|
| assay ≥99% (HPLC) | assay ≥99% | assay ≥98% (HPLC) | assay ≥98% (TLC) |
| Gene Information human ... PRKAR1A(5573), PRKAR1AP(5574), PRKAR1B(5575), PRKAR2A(5576), PRKAR2B(5577) | Gene Information rat ... Adora1(29290), Adora2a(25369) | Gene Information - | Gene Information - |
| Quality Level 200 | Quality Level 200 | Quality Level 100 | Quality Level 100 |
| form powder | form - | form solid | form solid |
| storage temp. −20°C | storage temp. −20°C | storage temp. −20°C | storage temp. 10-30°C |
| solubility DMSO: 1 M (with gentle warming), ethanol: 10 mg/mL | solubility DMSO: soluble 1 M (with gentle warming) | solubility ethanol: 10 mg/mL, DMSO: 100 mM, methanol: 50 mg/mL | solubility ethanol: 2 mg/mL, DMSO: 5 mg/mL |
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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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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)
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)
Global Trade Item Number
| SKU | GTIN |
|---|---|
| I5879-250MG | 04061835557387 |
| I5879-100MG | 04061835518166 |
| I5879-1G | 04061833857588 |
| I5879-5X5G | 04061832947945 |
| I5879-5G | 04061833857595 |
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Is this product sterile?
1 answer-
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After dissolving 3-Isobutyl-1-méthylxanthine (I5879) in DMSO or in pre-warmed methanol, where should it be stored (long term or short term)?
1 answer-
Solutions in DMSO may be stored at -20 °C. The stability of this material in methanol has not been investigated. However, an external publication reports storage of IBMX solutions in ethanol at 0.125 mg/mL at 4 °C for at least three months. Please see the link below to review additional information available in the product datasheet:
https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/product/documents/110/425/i5879pis-ms.pdfHelpful?
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HPにはDMSOへの溶解度は1 Mと記載されています。 https://www.sigmaaldrich.com/JP/ja/product/sigma/i5879#product-documentation 上記HPからダウンロードしたデータシートにはDMSOへの溶解度は200 mMと記載されています。 メーカー推奨の溶解度はどちらになりますでしょうか。
1 answer-
This material is soluble at a maximum concentration of 1M in DMSO. The 200 mM concentration is cited in Plouffe, B. et al., Methods Enzymol., 484, 295-328 (2010).
This concentration is sufficient for most applications. The product is tested for solubility in pre-warmed methanol at 50 mg/mL. The preferred solvent and stock concentration is dependent upon the application and requirements of the end user. Please see the link below to review additional information provided in the product information sheet:
https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/product/documents/110/425/i5879pis-ms.pdfHelpful?
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Is Product No. I5879, 3-Isobutyl-1-methylxanthine, appropriate for cell culture use?
1 answer-
Product No. I5879 is not a cell culture tested product. However, customers may wish to try this product in their cell culture applications.
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What is the difference between 3-Isobutyl-1-methylxanthine Product I5879 and I7018?
1 answer-
Product No. I5879 is reagent grade. Product No. I7018, SigmaUltra grade, has been subjected to additional testing for trace metal impurities.
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What is the Department of Transportation shipping information for this product?
1 answer-
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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What is the expiration date of Product No. I5879, 3-Isobutyl-1-methylxanthine?
1 answer-
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.
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