MSX-3 | CA#261717-23-1 | A2A antagonist

MedKoo Cat#: 563387 | Name: MSX-3

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Description:

WARNING: This product is for research use only, not for human or veterinary use.

MSX-3 is an A2A adenosine receptor antagonist and a prodrug of MSX-2.

Chemical Structure

MSX-3

CAS#261717-23-1

Theoretical Analysis

MedKoo Cat#: 563387

Name: MSX-3

CAS#: 261717-23-1

Chemical Formula: C21H21N4Na2O7P

Exact Mass:

Molecular Weight: 518.37

Elemental Analysis: C, 48.66; H, 4.08; N, 10.81; Na, 8.87; O, 21.60; P, 5.98

Price and Availability

Size	Price	Availability
5mg	USD 365.00	2 Weeks
10mg	USD 600.00	2 Weeks
25mg	USD 1,105.00	2 Weeks
50mg	USD 2,000.00	2 Weeks
100mg	USD 3,500.00	2 Weeks

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Related CAS #

No Data

Synonym

MSX-3; MSX 3; MSX3;

IUPAC/Chemical Name

3,7-Dihydro-8-[(1E)-2-(3-methoxyphenyl)ethenyl]-7-methyl-3-[3-(phosphonooxy)propyl]-1-(2-propynyl)-1H-purine-2,6-dione Disodium Salt

InChi Key

ZYVZWCILYQDHNU-TTWKNDKESA-L

InChi Code

InChI=1S/C21H23N4O7P.2Na/c1-4-11-25-20(26)18-19(24(21(25)27)12-6-13-32-33(28,29)30)22-17(23(18)2)10-9-15-7-5-8-16(14-15)31-3;;/h1,5,7-10,14H,6,11-13H2,2-3H3,(H2,28,29,30);;/q;2*+1/p-2/b10-9+;;

SMILES Code

O=C(N1CC#C)N(CCCOP([O-])([O-])=O)C2=C(N(C)C(/C=C/C3=CC=CC(OC)=C3)=N2)C1=O.[Na+].[Na+]

Appearance

Solid powder

Purity

>98% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility

Soluble in DMSO

Shelf Life

>3 years if stored properly

Drug Formulation

This drug may be formulated in DMSO

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.03.00

More Info

Product Data

Product Data

Instruction

View handling instruction

Biological target:

MSX-3 is an A2A adenosine receptor antagonist and a prodrug of MSX-2.

In vitro activity:

TBD

In vivo activity:

In LPS vehicle treated rats (saline, i.p.), MSX-3 enhanced pLTF versus controls (LPS: 110 ± 16% baseline; controls: 53 ± 6%; p=0.002; n=6/group). In LPS-treated rats, pLTF (phrenic long-term facilitation) was abolished as expected (4 ± 6% baseline; n=6), but intrathecal MSX-3 restored pLTF to levels equivalent to MSX-3 treated control rats (120 ± 14% baseline; p<0.001; n=6; vs LPS controls with MSX-3: p=0.539). Reference: J Neurophysiol. 2023 Mar 8. https://pubmed.ncbi.nlm.nih.gov/36883762/

Preparing Stock Solutions

The following data is based on the product molecular weight 518.37 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

Formulation protocol:

1. Marciante AB, Mitchell GS. Mild inflammation impairs acute intermittent hypoxia-induced phrenic long-term facilitation by a spinal adenosine-dependent mechanism. J Neurophysiol. 2023 Mar 8. doi: 10.1152/jn.00035.2023. Epub ahead of print. PMID: 36883762. 2. Mitchell LJ, Mayer CA, Mayer A, Di Fiore JM, Shein SL, Raffay TM, MacFarlane PM. Caffeine prevents prostaglandin E1-induced disturbances in respiratory control in neonatal rats: implications for infants with critical congenital heart disease. Am J Physiol Regul Integr Comp Physiol. 2020 Aug 1;319(2):R233-R242. doi: 10.1152/ajpregu.00316.2019. Epub 2020 Jun 24. PMID: 32579854; PMCID: PMC7473891.

In vitro protocol:

TBD

In vivo protocol:

1: Agosto-Marlin IM, Nichols NL, Mitchell GS. Adenosine-dependent phrenic motor facilitation is inflammation resistant. J Neurophysiol. 2017 Feb 1;117(2):836-845. doi: 10.1152/jn.00619.2016. Epub 2016 Dec 7. PubMed PMID: 27927784; PubMed Central PMCID: PMC5315699. 2: López-Cruz L, San-Miguel N, Bayarri P, Baqi Y, Müller CE, Salamone JD, Correa M. Ethanol and Caffeine Effects on Social Interaction and Recognition in Mice: Involvement of Adenosine A(2A) and A(1) Receptors. Front Behav Neurosci. 2016 Nov 2;10:206. eCollection 2016. PubMed PMID: 27853423; PubMed Central PMCID: PMC5090123. 3: Yohn SE, Arif Y, Haley A, Tripodi G, Baqi Y, Müller CE, Miguel NS, Correa M, Salamone JD. Effort-related motivational effects of the pro-inflammatory cytokine interleukin-6: pharmacological and neurochemical characterization. Psychopharmacology (Berl). 2016 Oct;233(19-20):3575-86. doi: 10.1007/s00213-016-4392-9. Epub 2016 Aug 6. PubMed PMID: 27497935. 4: Devinney MJ, Nichols NL, Mitchell GS. Sustained Hypoxia Elicits Competing Spinal Mechanisms of Phrenic Motor Facilitation. J Neurosci. 2016 Jul 27;36(30):7877-85. doi: 10.1523/JNEUROSCI.4122-15.2016. PubMed PMID: 27466333; PubMed Central PMCID: PMC4961775. 5: Podurgiel SJ, Spencer T, Kovner R, Baqi Y, Müller CE, Correa M, Salamone JD. Induction of oral tremor in mice by the acetylcholinesterase inhibitor galantamine: Reversal with adenosine A2A antagonism. Pharmacol Biochem Behav. 2016 Jan;140:62-7. doi: 10.1016/j.pbb.2015.10.008. Epub 2015 Oct 13. PubMed PMID: 26459156. 6: Fritz BM, Boehm SL 2nd. Adenosinergic regulation of binge-like ethanol drinking and associated locomotor effects in male C57BL/6J mice. Pharmacol Biochem Behav. 2015 Aug;135:83-9. doi: 10.1016/j.pbb.2015.05.016. Epub 2015 May 29. PubMed PMID: 26033424; PubMed Central PMCID: PMC4492850. 7: Fuzzati-Armentero MT, Cerri S, Levandis G, Ambrosi G, Montepeloso E, Antoninetti G, Blandini F, Baqi Y, Müller CE, Volpini R, Costa G, Simola N, Pinna A. Dual target strategy: combining distinct non-dopaminergic treatments reduces neuronal cell loss and synergistically modulates L-DOPA-induced rotational behavior in a rodent model of Parkinson's disease. J Neurochem. 2015 Aug;134(4):740-7. doi: 10.1111/jnc.13162. Epub 2015 Jun 4. PubMed PMID: 25962878. 8: Laurent C, Burnouf S, Ferry B, Batalha VL, Coelho JE, Baqi Y, Malik E, Mariciniak E, Parrot S, Van der Jeugd A, Faivre E, Flaten V, Ledent C, D'Hooge R, Sergeant N, Hamdane M, Humez S, Müller CE, Lopes LV, Buée L, Blum D. A2A adenosine receptor deletion is protective in a mouse model of Tauopathy. Mol Psychiatry. 2016 Jan;21(1):97-107. doi: 10.1038/mp.2014.151. Epub 2014 Dec 2. Erratum in: Mol Psychiatry. 2016 Jan;21(1):149. Mariciniak, E [Corrected to Marciniak, E]. PubMed PMID: 25450226. 9: Yohn SE, Thompson C, Randall PA, Lee CA, Müller CE, Baqi Y, Correa M, Salamone JD. The VMAT-2 inhibitor tetrabenazine alters effort-related decision making as measured by the T-maze barrier choice task: reversal with the adenosine A2A antagonist MSX-3 and the catecholamine uptake blocker bupropion. Psychopharmacology (Berl). 2015 Apr;232(7):1313-23. doi: 10.1007/s00213-014-3766-0. Epub 2014 Oct 17. PubMed PMID: 25323625. 10: Clissold KA, Pratt WE. The effects of nucleus accumbens μ-opioid and adenosine 2A receptor stimulation and blockade on instrumental learning. Behav Brain Res. 2014 Nov 1;274:84-94. doi: 10.1016/j.bbr.2014.07.047. Epub 2014 Aug 4. PubMed PMID: 25101542; PubMed Central PMCID: PMC4181594. 11: Randall PA, Lee CA, Nunes EJ, Yohn SE, Nowak V, Khan B, Shah P, Pandit S, Vemuri VK, Makriyannis A, Baqi Y, Müller CE, Correa M, Salamone JD. The VMAT-2 inhibitor tetrabenazine affects effort-related decision making in a progressive ratio/chow feeding choice task: reversal with antidepressant drugs. PLoS One. 2014 Jun 17;9(6):e99320. doi: 10.1371/journal.pone.0099320. eCollection 2014. PubMed PMID: 24937131; PubMed Central PMCID: PMC4061002. 12: Justinová Z, Redhi GH, Goldberg SR, Ferré S. Differential effects of presynaptic versus postsynaptic adenosine A2A receptor blockade on Δ9-tetrahydrocannabinol (THC) self-administration in squirrel monkeys. J Neurosci. 2014 May 7;34(19):6480-4. doi: 10.1523/JNEUROSCI.5073-13.2014. PubMed PMID: 24806674; PubMed Central PMCID: PMC4012307. 13: Cerri S, Levandis G, Ambrosi G, Montepeloso E, Antoninetti GF, Franco R, Lanciego JL, Baqi Y, Müller CE, Pinna A, Blandini F, Armentero MT. Neuroprotective potential of adenosine A2A and cannabinoid CB1 receptor antagonists in an animal model of Parkinson disease. J Neuropathol Exp Neurol. 2014 May;73(5):414-24. doi: 10.1097/NEN.0000000000000064. PubMed PMID: 24709676. 14: Nichols NL, Johnson RA, Satriotomo I, Mitchell GS. Neither serotonin nor adenosine-dependent mechanisms preserve ventilatory capacity in ALS rats. Respir Physiol Neurobiol. 2014 Jun 15;197:19-28. doi: 10.1016/j.resp.2014.03.005. Epub 2014 Mar 28. PubMed PMID: 24681328; PubMed Central PMCID: PMC4022482. 15: Pinna A, Bonaventura J, Farré D, Sánchez M, Simola N, Mallol J, Lluís C, Costa G, Baqi Y, Müller CE, Cortés A, McCormick P, Canela EI, Martínez-Pinilla E, Lanciego JL, Casadó V, Armentero MT, Franco R. L-DOPA disrupts adenosine A(2A)-cannabinoid CB(1)-dopamine D(2) receptor heteromer cross-talk in the striatum of hemiparkinsonian rats: biochemical and behavioral studies. Exp Neurol. 2014 Mar;253:180-91. doi: 10.1016/j.expneurol.2013.12.021. Epub 2014 Jan 9. PubMed PMID: 24412491. 16: Nunes EJ, Randall PA, Hart EE, Freeland C, Yohn SE, Baqi Y, Müller CE, López-Cruz L, Correa M, Salamone JD. Effort-related motivational effects of the VMAT-2 inhibitor tetrabenazine: implications for animal models of the motivational symptoms of depression. J Neurosci. 2013 Dec 4;33(49):19120-30. doi: 10.1523/JNEUROSCI.2730-13.2013. PubMed PMID: 24305809; PubMed Central PMCID: PMC3850037. 17: Nunes EJ, Randall PA, Estrada A, Epling B, Hart EE, Lee CA, Baqi Y, Müller CE, Correa M, Salamone JD. Effort-related motivational effects of the pro-inflammatory cytokine interleukin 1-beta: studies with the concurrent fixed ratio 5/ chow feeding choice task. Psychopharmacology (Berl). 2014 Feb;231(4):727-36. doi: 10.1007/s00213-013-3285-4. Epub 2013 Oct 18. PubMed PMID: 24136220; PubMed Central PMCID: PMC4468782. 18: Podurgiel SJ, Nunes EJ, Yohn SE, Barber J, Thompson A, Milligan M, Lee CA, López-Cruz L, Pardo M, Valverde O, Lendent C, Baqi Y, Müller CE, Correa M, Salamone JD. The vesicular monoamine transporter (VMAT-2) inhibitor tetrabenazine induces tremulous jaw movements in rodents: implications for pharmacological models of parkinsonian tremor. Neuroscience. 2013 Oct 10;250:507-19. doi: 10.1016/j.neuroscience.2013.07.008. Epub 2013 Jul 15. PubMed PMID: 23867769. 19: Collins-Praino LE, Paul NE, Ledgard F, Podurgiel SJ, Kovner R, Baqi Y, Müller CE, Senatus PB, Salamone JD. Deep brain stimulation of the subthalamic nucleus reverses oral tremor in pharmacological models of parkinsonism: interaction with the effects of adenosine A2A antagonism. Eur J Neurosci. 2013 Jul;38(1):2183-91. doi: 10.1111/ejn.12212. Epub 2013 Apr 18. PubMed PMID: 23600953. 20: Pardo M, López-Cruz L, Valverde O, Ledent C, Baqi Y, Müller CE, Salamone JD, Correa M. Effect of subtype-selective adenosine receptor antagonists on basal or haloperidol-regulated striatal function: studies of exploratory locomotion and c-Fos immunoreactivity in outbred and A(2A)R KO mice. Behav Brain Res. 2013 Jun 15;247:217-26. doi: 10.1016/j.bbr.2013.03.035. Epub 2013 Apr 1. PubMed PMID: 23557694.