MSX-4 is a selective adenosine A2A receptor antagonist used in scientific research.[1] It is a water-soluble amino acid ester prodrug of MSX-2, the active metabolite of the drug.[2][1] MSX-4 reverses the motivational deficits induced by the dopamine D2 receptor antagonist eticlopride in animals and hence has the capacity to produce pro-motivational effects.[3][4] MSX-4 was first described in the scientific literature by 2008.[1]

MSX-4
Clinical data
Drug classAdenosine A2A receptor antagonist
Identifiers
  • L-valine-3-{8-[(E)-2-[3-methoxyphenyl)ethenyl]-7-methyl-1-propargylxanthine-3-yl}propyl ester
CAS Number
Chemical and physical data
FormulaC26H30N5O5
Molar mass492.556 g·mol−1
3D model (JSmol)
  • COC1=CC=CC(/C=C/C2N(C)C3=C(N(CCCOC(=O)[C@](C(C)C)N([H])[H])C(=O)N(CC#C)C3=O)N=2)=C1
  • InChI=APBGNHUAEAMEBF-VAWYXSNFSA-N
  • Key:1S/C26H30N5O5/c1-6-13-31-24(32)22-23(30(26(31)34)14-8-15-36-25(33)21(27)17(2)3)28-20(29(22)4)12-11-18-9-7-10-19(16-18)35-5/h1,7,9-12,16-17H,8,13-15,27H2,2-5H3/b12-11+

See also

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References

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  1. ^ a b c Vollmann K, Qurishi R, Hockemeyer J, Müller CE (February 2008). "Synthesis and properties of a new water-soluble prodrug of the adenosine A 2A receptor antagonist MSX-2". Molecules. 13 (2): 348–359. doi:10.3390/molecules13020348. PMC 6244838. PMID 18305423.
  2. ^ Müller CE (November 2009). "Prodrug approaches for enhancing the bioavailability of drugs with low solubility". Chemistry & Biodiversity. 6 (11): 2071–2083. doi:10.1002/cbdv.200900114. PMID 19937841.
  3. ^ Salamone JD, Correa M, Ferrigno S, Yang JH, Rotolo RA, Presby RE (October 2018). "The Psychopharmacology of Effort-Related Decision Making: Dopamine, Adenosine, and Insights into the Neurochemistry of Motivation". Pharmacol Rev. 70 (4): 747–762. doi:10.1124/pr.117.015107. PMC 6169368. PMID 30209181.
  4. ^ Santerre JL, Nunes EJ, Kovner R, Leser CE, Randall PA, Collins-Praino LE, Lopez Cruz L, Correa M, Baqi Y, Müller CE, Salamone JD (October 2012). "The novel adenosine A(2A) antagonist prodrug MSX-4 is effective in animal models related to motivational and motor functions". Pharmacol Biochem Behav. 102 (4): 477–487. doi:10.1016/j.pbb.2012.06.009. PMID 22705392.