IBMX

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

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

IBMX

Skeletal formula of IBMX Space-filling model of the IBMX model
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^Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:34795^Y
ChEMBL	ChEMBL275084^Y
ChemSpider	3627^Y
DrugBank	DB07954^Y
ECHA InfoCard	100.044.767
IUPHAR/BPS	388
KEGG	C13708^Y
PubChem CID	3758
UNII	TBT296U68M^Y
CompTox Dashboard (EPA)	DTXSID0040549
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)^Y Key: APIXJSLKIYYUKG-UHFFFAOYSA-N^Y 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 CC(C)Cn1c2c(c(=O)n(c1=O)C)[nH]cn2
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).
Y verify (what is ^YN ?)
Infobox references

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

References

1. Essayan, DM (November 2001). "Cyclic Nucleotide Phosphodiesterases". The Journal of Allergy and Clinical Immunology. 108 (5): 671–80. doi:10.1067/mai.2001.119555. PMID 11692087.
2. Deree, J; Martins, JO; Melbostad, H; Loomis, WH; Coimbra, R (June 2008). "Insights into the Regulation of TNF-α Production in Human Mononuclear Cells: The Effects of Non-Specific Phosphodiesterase Inhibition". Clinics (São Paulo, Brazil). 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-α Production from Human Alveolar Macrophages". American Journal of Respiratory and Critical Care Medicine. 159 (2): 508–11. doi:10.1164/ajrccm.159.2.9804085. PMID 9927365.
4. Peters-Golden, M; Canetti, C; Mancuso, P; Coffey, MJ (15 January 2005). "Leukotrienes: Underappreciated Mediators of Innate Immune Responses" (PDF). Journal of Immunology. 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". Progress in Clinical and Biological Research. 230: 41–63. PMID 3588607.
6. Beavo, JA; Rogers, NL; Crofford, OB; Hardman, JG; Sutherland, EW; Newman, EV (November 1970). "Effects of Xanthine Derivatives on Lipolysis and on Adenosine 3',5'-Monophosphate Phosphodiesterase Activity". Molecular Pharmacology. 6 (6): 597–603. PMID 4322367.
7. Soderling, SH; Beavo, JA (April 2000). "Regulation of cAMP and cGMP Signaling: New Phosphodiesterases and New Functions". Current Opinion in Cell Biology. 12 (2): 174–9. doi:10.1016/s0955-0674(99)00073-3. PMID 10712916.