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 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:34795 ;
ChEMBL	ChEMBL275084 ;
ChemSpider	3627 ;
DrugBank	DB07954 ;
ECHA InfoCard	100.044.767
IUPHAR/BPS	388;
KEGG	C13708 ;
PubChem CID	3758;
UNII	TBT296U68M ;
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) 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 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). verify (what is ?) Infobox references

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

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
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

^ 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.
^ 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 (Sao Paulo). 63 (3): 321–8. doi:10.1590/S1807-59322008000300006. PMC 2664230. PMID 18568240.
^ 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.
^ ^a ^b 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.
^ 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.
^ 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.
^ 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.

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[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 (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-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.

[Peters-Golden-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.

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