IBMX

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 checkY
3D model (JSmol)
  • Interactive image
ChEBI
  • CHEBI:34795 checkY
ChEMBL
  • ChEMBL275084 checkY
ChemSpider
  • 3627 checkY
DrugBank
  • DB07954 checkY
ECHA InfoCard 100.044.767 Edit this at Wikidata
IUPHAR/BPS
  • 388
KEGG
  • C13708 checkY
PubChem CID
  • 3758
UNII
  • TBT296U68M checkY
CompTox Dashboard (EPA)
  • DTXSID0040549 Edit this at Wikidata
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) checkY
    Key: APIXJSLKIYYUKG-UHFFFAOYSA-N checkY
  • 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
  • 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).
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Infobox references
Chemical compound

IBMX (3-isobutyl-1-methylxanthine), like other methylxanthine 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]

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 (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.
  4. ^ 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.
  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.
  • v
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PDE1PDE2
PDE3PDE4
PDE5PDE7PDE9PDE10
PDE11
BC11-38
Non-selectiveUnsorted
See also: Receptor/signaling modulators
  • v
  • t
  • e
Receptor
(ligands)
P0 (adenine)
P1
(adenosine)
P2
(nucleotide)
P2X
(ATPTooltip Adenosine triphosphate)
P2Y
Transporter
(blockers)
CNTsTooltip Concentrative nucleoside transporters
ENTsTooltip Equilibrative nucleoside transporters
PMATTooltip Plasma membrane monoamine transporter
Enzyme
(inhibitors)
XOTooltip Xanthine oxidase
Others
Others
See also: Receptor/signaling modulators


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