IBMX A potent inhibitor of phosphodiesterases

IBMX (CAS 28822-58-4)

IBMX | CAS 28822-58-4 is rated 5.0 out of 5 by 1.
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Synonym: 3-Isobutyl-1-methylanxthine; Methylisobutylxanthine; MIX
Application: A potent inhibitor of phosphodiesterases
CAS Number: 28822-58-4
Purity: ≥99%
Molecular Weight: 222.24
Molecular Formula: C10H14N4O2
* Refer to Certificate of Analysis for lot specific data (including water content).
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IBMX is one of the most potent and nonspecific inhibitors of cyclic nucleotide PDE (phosphodiesterases) with documented IC50 values for PDE1, 2, 3, 4, and 5 equaling 19, 50, 18, 13 and 32. The compound is documented to raise intracellular cyclic AMP levels. In rat sensory neurons the addition of IBMX caused the release of Ca2+ from caffeine ryanodine sensitive internal stores increasing the internal Ca2+ levels and inducing a biphasic membrane current response. Through PDE inhibition IBMX has also inhibited TNFα. IBMX in breast cancer cells has also induced p21 and p27 through a PKA independent pathway. Although a nonspecific PDE inhibitor IBMX does not show inhibition of PDE8B. In neuroendocrine epithelial cells IBMX has been observed to inhibit α-adrenoceptor-mediated 5-HT release at IC50 = 1.3μM.


References

1. Beavo, J.A., et al. 1970. Mol. Pharmacol. 6: 597-603. PMID: 4322367
2. Usachev, Y., et al. 1995. Pflugers Arch. 430: 420-428. PMID: 7491267
3. Rao, S., et al. 1999. Exp. Cell Res. 252: 211-223. PMID: 10502413
4. Freitag, A., et al. 1998. Eur. J. Pharmacol. 354: 67-71. PMID: 9726632

Physical State :
Solid
Solubility :
Soluble in ethanol (10 mg/ml), DMSO(with gentle warming) (1 M), methanol(warm) (50 mg/ml), 2-propanol, dichloromethane, ether, ethyl acetate, and DMF (~5 mg/ml). Insoluble in water.
Storage :
Store at room temperature
Melting Point :
200-201° C (lit.)
Boiling Point :
445.6° C at 760 mmHg (Predicted)
Density :
1.3 g/cm3 (Predicted)
Refractive Index :
n20D 1.57 (Predicted)
IC50 :
suppresses α-adrenoceptor-mediated 5-HT release: IC50 = 1.3 µM (neuroendocrine epithelial cells); PDE4: IC50 = 13 µM; PDE3: IC50 = 18 µM; PDE1: IC50 = 19 µM; PDE5 : IC50 = 32 µM; PDE2: IC50 = 50 µM; Phosphodiesterase 1B: IC50 = 100 nM (rat); Sodium channel protein type II alpha subunit: IC50 = 1800 nM (human)
Ki Data :
Adenosine A2b receptor: Ki= 50 nM (rat); Adenosine A2a receptor: Ki= 800 nM (rat); Adenosine A1 receptor: Ki= 2000 nM (rat)
pK Values :
pKa: 8.61 (Predicted), pKb: 1.49 (Predicted)
For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.
WGK Germany :
3
RTECS :
ZD8500000
PubChem CID :
3758
MDL Number :
MFCD00005584
EC Number :
249-259-3
Beilstein Registry :
247859
SMILES :
CC(C)CN1C2=C(C(=O)N(C1=O)C)NC=N2

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IBMX  Product Citations

See how others have used IBMX. Click on the entry to view the PubMed entry .

Citations 1 to 6 of 6 total

PMID: # 28730281  Świerczek, A. et al. 2017. Naunyn Schmiedebergs Arch. Pharmacol.

PMID: # 26481310  Liu, Z. et al. 2016. FASEB journal : official publication of the Federation of American Societies for Experimental Biology. 30: 635-52.

PMID: # 27125215  Wu, M. et al. 2016. Pflugers Arch.

PMID: # 27408772  Kolic, J. et al. 2016. Mol Metab. 5: 459-71.

PMID: # 26408789  Wang, X. et al. 2015. Toxicol. Appl. Pharmacol. 289: 286-96.

PMID: # 22261727  Rani, MP. et al. 2012. J. Sci. Food Agric. 92: 1948-55.

Citations 1 to 6 of 6 total

What is the expected appearance of this product?

Asked by: chemicalsmg
Thank you for your question. IBMX: sc-201188 is expected to be a white to off-white solid.
Answered by: Chemical Support 3
Date published: 2017-04-05

What is the appropriate temperature when you say it will dissolve in DMSO with gentle warming?

Asked by: SCchem16
Thank you for your question. IBMX, sc-201188, can be dissolved in DMSO warmed to ~37ºC.
Answered by: TechService7
Date published: 2017-02-14
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Rated 5 out of 5 by from Freitag et al Freitag et al. (PubMed ID 9726632) used IBMX to regulate cyclic nucleotide mediated inhibition of 5-HT release from neuroendocrine cells by inhibiting phosphodiesterase. -SCBT Publication Review
Date published: 2015-05-31
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