MSX-4

{{Short description|Selective adenosine A2A receptor antagonist}}

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| class = Adenosine A_2A receptor antagonist

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| CAS_number = 1072907-79-9

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| IUPAC_name = L-valine-3-{8-[(E)-2-[3-methoxyphenyl)ethenyl]-7-methyl-1-propargylxanthine-3-yl}propyl ester

| C=26 | H=30 | N=5 | O=5

| SMILES = 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

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| StdInChI = 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+

| StdInChIKey_Ref =

| StdInChIKey = APBGNHUAEAMEBF-VAWYXSNFSA-N

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MSX-4 is a selective adenosine A_2A receptor antagonist used in scientific research.{{cite journal | vauthors = Vollmann K, Qurishi R, Hockemeyer J, Müller CE | title = Synthesis and properties of a new water-soluble prodrug of the adenosine A 2A receptor antagonist MSX-2 | journal = Molecules | volume = 13 | issue = 2 | pages = 348–359 | date = February 2008 | pmid = 18305423 | pmc = 6244838 | doi = 10.3390/molecules13020348 | doi-access = free | url = }} It is a water-soluble amino acid ester prodrug of MSX-2, the active metabolite of the drug.{{cite journal | vauthors = Müller CE | title = Prodrug approaches for enhancing the bioavailability of drugs with low solubility | journal = Chemistry & Biodiversity | volume = 6 | issue = 11 | pages = 2071–2083 | date = November 2009 | pmid = 19937841 | doi = 10.1002/cbdv.200900114 }} 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.{{cite journal | vauthors = Salamone JD, Correa M, Ferrigno S, Yang JH, Rotolo RA, Presby RE | title = The Psychopharmacology of Effort-Related Decision Making: Dopamine, Adenosine, and Insights into the Neurochemistry of Motivation | journal = Pharmacol Rev | volume = 70 | issue = 4 | pages = 747–762 | date = October 2018 | pmid = 30209181 | pmc = 6169368 | doi = 10.1124/pr.117.015107 | url = }}{{cite journal | vauthors = Santerre JL, Nunes EJ, Kovner R, Leser CE, Randall PA, Collins-Praino LE, Lopez Cruz L, Correa M, Baqi Y, Müller CE, Salamone JD | title = The novel adenosine A(2A) antagonist prodrug MSX-4 is effective in animal models related to motivational and motor functions | journal = Pharmacol Biochem Behav | volume = 102 | issue = 4 | pages = 477–487 | date = October 2012 | pmid = 22705392 | doi = 10.1016/j.pbb.2012.06.009 | url = }} MSX-4 was first described in the scientific literature by 2008.