IBMX

IBMX

Names
IUPAC name 1-methyl-3-(2-methylpropyl)-7H-purine-2,6-dione
Other names 3-Isobutyl-1-methylxanthine
Identifiers
CAS Number	28822-58-4
ChEBI	CHEBI:34795
ChEMBL	ChEMBL275084
ChemSpider	3627
DrugBank	DB07954
IUPHAR/BPS	388
Jmol interactive 3D	Image
KEGG	C13708
PubChem	3758
UNII	TBT296U68M
InChI 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) Key: APIXJSLKIYYUKG-UHFFFAOYSA-N InChI=1/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) Key: APIXJSLKIYYUKG-UHFFFAOYAL
SMILES O=C2N(c1ncnc1C(=O)N2C)CC(C)C
Properties
Chemical formula	C10H14N4O2
Molar mass	222.3 g/mol
Appearance	White solid
Melting point	199 to 201 °C (390 to 394 °F; 472 to 474 K)
Solubility	Soluble in ethanol, DMSO, and methanol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

IBMX, 3-isobutyl-1-methylxanthine, like other methylated xanthine derivatives, is both a

1. competitive nonselective phosphodiesterase inhibitor ^[1] which raises intracellular cAMP, activates PKA, inhibits TNF-alpha ^[2][3] and leukotriene ^[4] synthesis, and reduces inflammation and innate immunity ^[4] and
2. nonselective adenosine receptor antagonist.^[5]

As a phosphodiesterase inhibitor, IBMX has IC₅₀ = 2-50 μM ^[6] and does not inhibit PDE8 or PDE9.^[7]

References

1. Essayan DM. (2001). "Cyclic nucleotide phosphodiesterases.". J Allergy Clin Immunol. 108 (5): 671–80. doi:10.1067/mai.2001.119555. PMID 11692087.
2. Deree J, Martins JO, Melbostad H, Loomis WH, Coimbra R. (2008). "Insights into the regulation of TNF-alpha production in human mononuclear cells: the effects of non-specific phosphodiesterase inhibition.". Clinics (Sao Paulo). 63 (3): 321–8. doi:10.1590/S1807-59322008000300006. PMC 2664230. PMID 18568240.
3. Marques LJ, Zheng L, Poulakis N, Guzman J, Costabel U (February 1999). "Pentoxifylline inhibits TNF-alpha production from human alveolar macrophages". Am. J. Respir. Crit. Care Med. 159 (2): 508–11. doi:10.1164/ajrccm.159.2.9804085. PMID 9927365.
4. Peters-Golden M, Canetti C, Mancuso P, Coffey MJ. (2005). "Leukotrienes: underappreciated mediators of innate immune responses.". J Immunol. 174 (2): 589–94. doi:10.4049/jimmunol.174.2.589. PMID 15634873.
5. Daly JW, Jacobson KA, Ukena D. (1987). "Adenosine receptors: development of selective agonists and antagonists.". Prog Clin Biol Res. 230 (1): 41–63. PMID 3588607.
6. Mol. Pharmacol 6: 597. 1970. Missing or empty |title= (help)
7. Soderling and Beavo Current Opinion in Cell Biol. 2000 12 174