Eglumetad monohydrate | LY354740 | mGlu2/3 agonist | CAS#209216-09-1

MedKoo Cat#: 127430 | Name: Eglumetad monohydrate

Description:

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

Eglumetad, also known as LY354740, is a research drug developed by Eli Lilly and Company, which is being investigated for its potential in the treatment of anxiety and drug addiction. It is a glutamate derived compound and its mode of action implies a novel mechanism.

Chemical Structure

Eglumetad monohydrate

CAS#209216-09-1 (hydrate)

Theoretical Analysis

MedKoo Cat#: 127430

Name: Eglumetad monohydrate

CAS#: 209216-09-1 (hydrate)

Chemical Formula: C8H13NO5

Exact Mass: 203.0794

Molecular Weight: 203.19

Elemental Analysis: C, 47.29; H, 6.45; N, 6.89; O, 39.37

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.

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Related CAS #

209216-09-1 (hydrate) 176199-48-7 (free base)

Synonym

Eglumetad monohydrate; Eglumegad hydrate; Eglumetad hydrate; LY-354740; LY354740; LY 354740;

IUPAC/Chemical Name

(1S,2S,5R,6S)-2-aminobicyclo[3.1.0]hexane-2,6-dicarboxylic acid hydrate

InChi Key

XJPQOSJARVVBIU-PLFKSMQJSA-N

InChi Code

InChI=1S/C8H11NO4.H2O/c9-8(7(12)13)2-1-3-4(5(3)8)6(10)11;/h3-5H,1-2,9H2,(H,10,11)(H,12,13);1H2/t3-,4-,5-,8-;/m0./s1

SMILES Code

O.[H][C@@]12CC[C@@](N)(C(O)=O)[C@]1([H])[C@H]2C(O)=O

Appearance

To be determined

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

To be determined

Shelf Life

>2 years if stored properly

Drug Formulation

To be determined

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 203.19 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: Orlando R, Borro M, Motolese M, Molinaro G, Scaccianoce S, Caruso A, di Nuzzo L, Caraci F, Matrisciano F, Pittaluga A, Mairesse J, Simmaco M, Nisticò R, Monn JA, Nicoletti F. Levels of the Rab GDP dissociation inhibitor (GDI) are altered in the prenatal restrain stress mouse model of schizophrenia and are differentially regulated by the mGlu2/3 receptor agonists, LY379268 and LY354740. Neuropharmacology. 2014 Nov;86:133-44. doi: 10.1016/j.neuropharm.2014.07.009. PubMed PMID: 25063582. 2: Procaccini C, Maksimovic M, Aitta-Aho T, Korpi ER, Linden AM. Reversal of novelty-induced hyperlocomotion and hippocampal c-Fos expression in GluA1 knockout male mice by the mGluR2/3 agonist LY354740. Neuroscience. 2013 Oct 10;250:189-200. doi: 10.1016/j.neuroscience.2013.07.010. PubMed PMID: 23867766. 3: Menezes MM, Santini MA, Benvenga MJ, Marek GJ, Merchant KM, Mikkelsen JD, Svensson KA. The mGlu2/3 Receptor Agonists LY354740 and LY379268 Differentially Regulate Restraint-Stress-Induced Expression of c-Fos in Rat Cerebral Cortex. Neurosci J. 2013;2013:736439. doi: 10.1155/2013/736439. PubMed PMID: 26317098; PubMed Central PMCID: PMC4437333. 4: Profaci CP, Krolikowski KA, Olszewski RT, Neale JH. Group II mGluR agonist LY354740 and NAAG peptidase inhibitor effects on prepulse inhibition in PCP and D-amphetamine models of schizophrenia. Psychopharmacology (Berl). 2011 Jul;216(2):235-43. doi: 10.1007/s00213-011-2200-0. PubMed PMID: 21327758; PubMed Central PMCID: PMC3108005. 5: Eriksson AH, Varma MV, Perkins EJ, Zimmerman CL. The intestinal absorption of a prodrug of the mGlu2/3 receptor agonist LY354740 is mediated by PEPT1: in situ rat intestinal perfusion studies. J Pharm Sci. 2010 Mar;99(3):1574-81. doi: 10.1002/jps.21917. PubMed PMID: 19780137. 6: Schlumberger C, Pietraszek M, Gravius A, Klein KU, Greco S, Morè L, Danysz W. Comparison of the mGlu(5) receptor positive allosteric modulator ADX47273 and the mGlu(2/3) receptor agonist LY354740 in tests for antipsychotic-like activity. Eur J Pharmacol. 2009 Nov 25;623(1-3):73-83. doi: 10.1016/j.ejphar.2009.09.006. PubMed PMID: 19765575. 7: Fell MJ, Perry KW, Falcone JF, Johnson BG, Barth VN, Rash KS, Lucaites VL, Threlkeld PG, Monn JA, McKinzie DL, Marek GJ, Svensson KA, Nelson DL. In vitro and in vivo evidence for a lack of interaction with dopamine D2 receptors by the metabotropic glutamate 2/3 receptor agonists 1S,2S,5R,6S-2-aminobicyclo[3.1.0]hexane-2,6-bicaroxylate monohydrate (LY354740) and (-)-2-oxa-4-aminobicyclo[3.1.0] Hexane-4,6-dicarboxylic acid (LY379268). J Pharmacol Exp Ther. 2009 Dec;331(3):1126-36. doi: 10.1124/jpet.109.160598. PubMed PMID: 19755662. 8: Schlumberger C, Schäfer D, Barberi C, Morè L, Nagel J, Pietraszek M, Schmidt WJ, Danysz W. Effects of a metabotropic glutamate receptor group II agonist LY354740 in animal models of positive schizophrenia symptoms and cognition. Behav Pharmacol. 2009 Feb;20(1):56-66. doi: 10.1097/FBP.0b013e3283242f57. PubMed PMID: 19179851. 9: Varma MV, Eriksson AH, Sawada G, Pak YA, Perkins EJ, Zimmerman CL. Transepithelial transport of the group II metabotropic glutamate 2/3 receptor agonist (1S,2S,5R,6S)-2-aminobicyclo[3.1.0]hexane-2,6-dicarboxylate (LY354740) and its prodrug (1S,2S,5R,6S)-2-[(2'S)-(2'-amino)propionyl]aminobicyclo[3.1.0]hexane-2,6-dicarbox ylate (LY544344). Drug Metab Dispos. 2009 Jan;37(1):211-20. doi: 10.1124/dmd.108.022012. PubMed PMID: 18838508. 10: Imre G, Fokkema DS, Ter Horst GJ. Subchronic administration of LY354740 does not modify ketamine-evoked behavior and neuronal activity in rats. Eur J Pharmacol. 2006 Aug 21;544(1-3):77-81. PubMed PMID: 16860791. 11: Marek GJ, Wright RA, Schoepp DD. 5-Hydroxytryptamine2A (5-HT2A) receptor regulation in rat prefrontal cortex: interaction of a phenethylamine hallucinogen and the metabotropic glutamate2/3 receptor agonist LY354740. Neurosci Lett. 2006 Aug 7;403(3):256-60. PubMed PMID: 16759803. 12: Linden AM, Baez M, Bergeron M, Schoepp DD. Effects of mGlu2 or mGlu3 receptor deletions on mGlu2/3 receptor agonist (LY354740)-induced brain c-Fos expression: specific roles for mGlu2 in the amygdala and subcortical nuclei, and mGlu3 in the hippocampus. Neuropharmacology. 2006 Aug;51(2):213-28. PubMed PMID: 16733060. 13: Lee Y, Duman RS, Marek GJ. The mGlu2/3 receptor agonist LY354740 suppresses immobilization stress-induced increase in rat prefrontal cortical BDNF mRNA expression. Neurosci Lett. 2006 May 8;398(3):328-32. PubMed PMID: 16469447. 14: Rorick-Kehn LM, Perkins EJ, Knitowski KM, Hart JC, Johnson BG, Schoepp DD, McKinzie DL. Improved bioavailability of the mGlu2/3 receptor agonist LY354740 using a prodrug strategy: in vivo pharmacology of LY544344. J Pharmacol Exp Ther. 2006 Feb;316(2):905-13. PubMed PMID: 16223873. 15: Bergink V, Westenberg HG. Metabotropic glutamate II receptor agonists in panic disorder: a double blind clinical trial with LY354740. Int Clin Psychopharmacol. 2005 Nov;20(6):291-3. PubMed PMID: 16192835. 16: Aggarwal VK, Grange E. Asymmetric sulfonium ylide mediated cyclopropanation: stereocontrolled synthesis of (+)-LY354740. Chemistry. 2005 Dec 23;12(2):568-75. PubMed PMID: 16187367. 17: van Berckel BN, Kegeles LS, Waterhouse R, Guo N, Hwang DR, Huang Y, Narendran R, Van Heertum R, Laruelle M. Modulation of amphetamine-induced dopamine release by group II metabotropic glutamate receptor agonist LY354740 in non-human primates studied with positron emission tomography. Neuropsychopharmacology. 2006 May;31(5):967-77. PubMed PMID: 16177807. 18: Bueno AB, Collado I, de Dios A, Domínguez C, Martín JA, Martín LM, Martínez-Grau MA, Montero C, Pedregal C, Catlow J, Coffey DS, Clay MP, Dantzig AH, Lindstrom T, Monn JA, Jiang H, Schoepp DD, Stratford RE, Tabas LB, Tizzano JP, Wright RA, Herin MF. Dipeptides as effective prodrugs of the unnatural amino acid (+)-2-aminobicyclo[3.1.0]hexane-2,6-dicarboxylic acid (LY354740), a selective group II metabotropic glutamate receptor agonist. J Med Chem. 2005 Aug 11;48(16):5305-20. PubMed PMID: 16078848. 19: Linden AM, Bergeron M, Schoepp DD. Comparison of c-Fos induction in the brain by the mGlu2/3 receptor antagonist LY341495 and agonist LY354740: evidence for widespread endogenous tone at brain mGlu2/3 receptors in vivo. Neuropharmacology. 2005;49 Suppl 1:120-34. PubMed PMID: 16023151. 20: Malherbe P, Richards JG, Broger C, Zenner MT, Messer J, Kratzeisen C, Nakanishi S, Mutel V. Opposite effects of Zn on the in vitro binding of [3H]LY354740 to recombinant and native metabotropic glutamate 2 and 3 receptors. J Neurochem. 2005 Jul;94(1):150-60. PubMed PMID: 15953358.