MSX-2

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Not to be confused with MSX2.
MSX-2
Clinical data
Other names3-(3-Hydroxypropyl)-7-methyl-8-(3-methoxystyryl)-1-propargylxanthine
Drug classAdenosine A2A receptor antagonist
Identifiers
  • 3-(3-hydroxypropyl)-8-[(E)-2-(3-methoxyphenyl)ethenyl]-7-methyl-1-prop-2-ynylpurine-2,6-dione
CAS Number
PubChem CID
IUPHAR/BPS
ChemSpider
ChEMBL
E number{{#property:P628}}
CompTox Dashboard (EPA)
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Chemical and physical data
FormulaC21H22N4O4
Molar mass394.431 g·mol−1
3D model (JSmol)
  • CN1C(=NC2=C1C(=O)N(C(=O)N2CCCO)CC#C)/C=C/C3=CC(=CC=C3)OC
  • InChI=1S/C21H22N4O4/c1-4-11-25-20(27)18-19(24(21(25)28)12-6-13-26)22-17(23(18)2)10-9-15-7-5-8-16(14-15)29-3/h1,5,7-10,14,26H,6,11-13H2,2-3H3/b10-9+
  • Key:FWLDDFYHEQMIGG-MDZDMXLPSA-N

MSX-2 is a selective adenosine A2A receptor antagonist used in scientific research.[1] It is a xanthine and a derivative of the non-selective adenosine receptor antagonist caffeine.[1][2]

The affinities (Ki) of MSX-2 for the human adenosine receptors are 5.38 to 14.5 nM for the adenosine A2A receptor, 2,500 nM for the adenosine A1 receptor (172- to 465-fold lower than for the A2A receptor), and >10,000 nM for the adenosine A2B and A3 receptors (>690-fold lower than for the A2A receptor).[3][4]

MSX-2 has poor water solubility, which has limited the use of MSX-2 itself.[1][5] Water-soluble ester prodrugs of MSX-2, including MSX-3 (a phosphate ester prodrug) and MSX-4 (an amino acid ester prodrug), have been developed and used in place of MSX-2.[1][5] MSX-3 is best-suited for use by intravenous administration, whereas MSX-4 can be administered by oral administration.[5][6]

MSX-3 and MSX-4 reverse motivational deficits in animals and hence have the capacity to produce pro-motivational effects.[7][8][9]

MSX-2 and MSX-3 were first described in the scientific literature by 1998.[10][11] Subsequently, MSX-4 was developed and described by 2008.[5][6]

See also

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References

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