(S)-AMPA | CAS# 83643-88-3 | AMPA agonist

MedKoo Cat#: 573832 | Name: (S)-AMPA

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Description:

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

(S)-AMPA is an active isomer of (RS)-AMPA and selective AMPA agonist.

Chemical Structure

(S)-AMPA

CAS#83643-88-3

Theoretical Analysis

MedKoo Cat#: 573832

Name: (S)-AMPA

CAS#: 83643-88-3

Chemical Formula: C7H10N2O4

Exact Mass: 186.0641

Molecular Weight: 186.17

Elemental Analysis: C, 45.16; H, 5.41; N, 15.05; O, 34.38

Price and Availability

Size	Price	Availability
1mg	USD 450.00	2 Weeks
10mg	USD 750.00	2 Weeks
50mg	USD 1,950.00	2 Weeks

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Related CAS #

77521-29-0 (racemic) 83654-13-1 (R isomer)

Synonym

(S)-AMPA, AMPA, L-; L-AMPA, S-AMPA

IUPAC/Chemical Name

4-Isoxazolepropanoic acid, alpha-amino-2,3-dihydro-5-methyl-3-oxo-, (S)-

InChi Key

UUDAMDVQRQNNHZ-YFKPBYRVSA-N

InChi Code

1S/C7H10N2O4/c1-3-4(6(10)9-13-3)2-5(8)7(11)12/h5H,2,8H2,1H3,(H,9,10)(H,11,12)/t5-/m0/s1

SMILES Code

Cc1onc(O)c1C[C@H](N)C(=O)O

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

2934.99.9001

More Info

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 186.17 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

1: Zhang J, Wang X, Bernardi RE, Ju J, Wei S, Gong Z. Activation of AMPA Receptors in the Lateral Habenula Produces Anxiolytic Effects in a Rat Model of Parkinson's Disease. Front Pharmacol. 2022 Jan 25;13:821975. doi: 10.3389/fphar.2022.821975. PMID: 35145415; PMCID: PMC8822149. 2: Hawkinson JE, Espitia SA. Effects of thiocyanate and AMPA receptor ligands on (S)-5-fluorowillardiine, (S)-AMPA and (R,S)-AMPA binding. Eur J Pharmacol. 1997 Jun 25;329(2-3):213-21. PMID: 9226415. 3: Brooks JW, Thompson SW, Rice AS, Malcangio M. (S)-AMPA inhibits electrically evoked calcitonin gene-related peptide (CGRP) release from the rat dorsal horn: reversal by cannabinoid receptor antagonist SR141716A. Neurosci Lett. 2004 Nov 30;372(1-2):85-8. doi: 10.1016/j.neulet.2004.09.014. PMID: 15531093. 4: Ebert B, Madsen U, Lund TM, Lenz SM, Krogsgaard-Larsen P. Molecular pharmacology of the AMPA agonist, (S)-2-amino-3-(3-hydroxy-5-phenyl-4-isoxazolyl)propionic acid [(S)-APPA] and the AMPA antagonist, (R)-APPA. Neurochem Int. 1994 Jun;24(6):507-15. doi: 10.1016/0197-0186(94)90001-9. PMID: 7526921. 5: Lockhart BP, Rodriguez M, Mourlevat S, Peron P, Catesson S, Villain N, Galizzi JP, Boutin JA, Lestage P. S18986: a positive modulator of AMPA-receptors enhances (S)-AMPA-mediated BDNF mRNA and protein expression in rat primary cortical neuronal cultures. Eur J Pharmacol. 2007 Apr 30;561(1-3):23-31. doi: 10.1016/j.ejphar.2007.01.030. Epub 2007 Feb 1. PMID: 17331496. 6: Zhang J, Lv S, Tang G, Bian G, Yang Y, Li R, Yang J, Liu J. Activation of calcium-impermeable GluR2-containing AMPA receptors in the lateral habenula produces antidepressant-like effects in a rodent model of Parkinson's disease. Exp Neurol. 2019 Dec;322:113058. doi: 10.1016/j.expneurol.2019.113058. Epub 2019 Sep 6. PMID: 31499061. 7: Larm JA, Cheung NS, Beart PM. (S)-5-fluorowillardiine-mediated neurotoxicity in cultured murine cortical neurones occurs via AMPA and kainate receptors. Eur J Pharmacol. 1996 Oct 24;314(1-2):249-54. doi: 10.1016/s0014-2999(96)00633-4. PMID: 8957243. 8: Lockhart B, Iop F, Closier M, Lestage P. (S)-2,3-dihydro-[3,4]cyclopentano-1,2,4-benzothiadiazine-1,1-dioxide: (S18986-1) a positive modulator of AMPA receptors enhances (S)-AMPA-mediated [3H]noradrenaline release from rat hippocampal and frontal cortex slices. Eur J Pharmacol. 2000 Aug 4;401(2):145-53. doi: 10.1016/s0014-2999(00)00433-7. PMID: 10924919. 9: Park YH, Mueller BH 2nd, McGrady NR, Ma HY, Yorio T. AMPA receptor desensitization is the determinant of AMPA receptor mediated excitotoxicity in purified retinal ganglion cells. Exp Eye Res. 2015 Mar;132:136-50. doi: 10.1016/j.exer.2015.01.026. Epub 2015 Jan 30. PMID: 25643624. 10: Cervetto C, Frattaroli D, Venturini A, Passalacqua M, Nobile M, Alloisio S, Tacchetti C, Maura G, Agnati LF, Marcoli M. Calcium-permeable AMPA receptors trigger vesicular glutamate release from Bergmann gliosomes. Neuropharmacology. 2015 Dec;99:396-407. doi: 10.1016/j.neuropharm.2015.08.011. Epub 2015 Aug 7. PMID: 26260232. 11: Chang Y, Du C, Han L, Lv S, Zhang J, Bian G, Tang G, Liu Y, Chen T, Liu J. Enhanced AMPA receptor-mediated excitatory transmission in the rodent rostromedial tegmental nucleus following lesion of the nigrostriatal pathway. Neurochem Int. 2019 Jan;122:85-93. doi: 10.1016/j.neuint.2018.11.007. Epub 2018 Nov 15. PMID: 30448565. 12: Summa M, Di Prisco S, Grilli M, Marchi M, Pittaluga A. Hippocampal AMPA autoreceptors positively coupled to NMDA autoreceptors traffic in a constitutive manner and undergo adaptative changes following enriched environment training. Neuropharmacology. 2011 Dec;61(8):1282-90. doi: 10.1016/j.neuropharm.2011.07.032. Epub 2011 Jul 30. PMID: 21820454. 13: Sinclair C, Reavy H, Grieve A, Schousboe A, Morelli E, Novellino E, Campiani G, Griffiths R. Inherent desensitisation-preventing properties of a novel, subtype-selective AMPA receptor agonist, (S)-CPW 399, as a possible explanation for its excitotoxic action in cultured cerebellar granule cells. Neurochem Int. 2003 May;42(6):499-510. doi: 10.1016/s0197-0186(02)00141-9. PMID: 12547649. 14: Hawkins LM, Beaver KM, Jane DE, Taylor PM, Sunter DC, Roberts PJ. Binding of the new radioligand (S)-[3H]AMPA to rat brain synaptic membranes: effects of a series of structural analogues of the non-NMDA receptor agonist willardiine. Neuropharmacology. 1995 Apr;34(4):405-10. doi: 10.1016/0028-3908(94)00157-n. PMID: 7566471. 15: Ishiwata S, Umino A, Nishikawa T. Involvement of neuronal and glial activities in control of the extracellular d-serine concentrations by the AMPA glutamate receptor in the mouse medial prefrontal cortex. Neurochem Int. 2018 Oct;119:120-125. doi: 10.1016/j.neuint.2017.09.009. Epub 2017 Sep 28. PMID: 28966065. 16: Araki R, Ago Y, Hasebe S, Nishiyama S, Tanaka T, Oka S, Takuma K, Matsuda T. Involvement of prefrontal AMPA receptors in encounter stimulation-induced hyperactivity in isolation-reared mice. Int J Neuropsychopharmacol. 2014 Jun;17(6):883-93. doi: 10.1017/S1461145713001582. Epub 2014 Jan 9. PMID: 24405605. 17: Mourlevat S, Galizzi JP, Guigal-Stéphan N, Courtade-Gaïani S, Rolland- Valognes G, Rodriguez M, Barbet F, Bourrier C, Catesson S, Chomel A, Danober L, Villain N, Caignard DH, Pirotte B, Lestage P, Lockhart BP. Molecular characterization of the AMPA-receptor potentiator S70340 in rat primary cortical culture: whole-genome expression profiling. Neurosci Res. 2011 Aug;70(4):349-60. doi: 10.1016/j.neures.2011.05.004. Epub 2011 May 14. PMID: 21609738. 18: Vogensen SB, Greenwood JR, Varming AR, Brehm L, Pickering DS, Nielsen B, Liljefors T, Clausen RP, Johansen TN, Krogsgaard-Larsen P. A stereochemical anomaly: the cyclised (R)-AMPA analogue (R)-3-hydroxy-4,5,6,7-tetrahydroisoxazolo[5,4-c]pyridine-5-carboxylic acid [(R)-5-HPCA] resembles (S)-AMPA at glutamate receptors. Org Biomol Chem. 2004 Jan 21;2(2):206-13. doi: 10.1039/b310450h. Epub 2003 Nov 24. PMID: 14737644. 19: Fischer W, Franke H, Scheibler P, Allgaier C, Illes P. AMPA-induced Ca(2+) influx in cultured rat cortical nonpyramidal neurones: pharmacological characterization using fura-2 microfluorimetry. Eur J Pharmacol. 2002 Mar 1;438(1-2):53-62. doi: 10.1016/s0014-2999(02)01296-7. PMID: 11906710. 20: Voss OP, Milne S, Sharkey J, O'Neill MJ, McCulloch J. Molecular mechanisms of neurite growth with AMPA receptor potentiation. Neuropharmacology. 2007 Feb;52(2):590-7. doi: 10.1016/j.neuropharm.2006.09.001. Epub 2006 Nov 13. PMID: 17101156.