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MedKoo Cat#: 527805 | Name: MGS-0039

Description:

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

MGS-0039, also known as BCI-632, is a group II metabotropic glutamate receptor (mgluR2/3) antagonist potentially for the treatment of cognitive disorders, depression and anxiety. Antidepressant-like action of group II mGlu receptor antagonists does not depend on serotonergic system activation. However, the AMPA receptor seems to play a key role in the antidepressant-like action of these compounds. Dopamine release in the NAc shell is regulated by mGlu 2/3 receptors.

Chemical Structure

MGS-0039
MGS-0039
CAS#569686-87-9

Theoretical Analysis

MedKoo Cat#: 527805

Name: MGS-0039

CAS#: 569686-87-9

Chemical Formula: C15H14Cl2FNO5

Exact Mass: 377.0233

Molecular Weight: 378.18

Elemental Analysis: C, 47.64; H, 3.73; Cl, 18.75; F, 5.02; N, 3.70; O, 21.15

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 #
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Synonym
MGS-0039; MGS 0039; MGS0039; BCI-632; BCI632; BCI 632
IUPAC/Chemical Name
(1R,2R,3R,5R,6R)-2-amino-3-((3,4-dichlorobenzyl)oxy)-6-fluorobicyclo[3.1.0]hexane-2,6-dicarboxylic acid
InChi Key
LFAGGDAZZKUVKO-JAGWWQSPSA-N
InChi Code
InChI=1S/C15H14Cl2FNO5/c16-8-2-1-6(3-9(8)17)5-24-10-4-7-11(14(7,18)12(20)21)15(10,19)13(22)23/h1-3,7,10-11H,4-5,19H2,(H,20,21)(H,22,23)/t7-,10-,11+,14-,15+/m1/s1
SMILES Code
O=C([C@@]1(N)[C@]2([H])[C@](C(O)=O)(F)[C@]2([H])C[C@H]1OCC3=CC=C(Cl)C(Cl)=C3)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
>2 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

Preparing Stock Solutions

The following data is based on the product molecular weight 378.18 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.

Recalculate based on batch purity %
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: Pałucha-Poniewiera A, Wierońska JM, Brański P, Stachowicz K, Chaki S, Pilc A. On the mechanism of the antidepressant-like action of group II mGlu receptor antagonist, MGS0039. Psychopharmacology (Berl). 2010 Dec;212(4):523-35. doi: 10.1007/s00213-010-1978-5. PubMed PMID: 20703449; PubMed Central PMCID: PMC2981731. 2: Koike H, Iijima M, Chaki S. Involvement of the mammalian target of rapamycin signaling in the antidepressant-like effect of group II metabotropic glutamate receptor antagonists. Neuropharmacology. 2011 Dec;61(8):1419-23. doi: 10.1016/j.neuropharm.2011.08.034. PubMed PMID: 21903115. 3: Stachowicz K, Wierońska J, Domin H, Chaki S, Pilc A. Anxiolytic-like activity of MGS0039, a selective group II mGlu receptor antagonist, is serotonin- and GABA-dependent. Pharmacol Rep. 2011;63(4):880-7. PubMed PMID: 22001975. 4: Shimazaki T, Kaku A, Chaki S. Blockade of the metabotropic glutamate 2/3 receptors enhances social memory via the AMPA receptor in rats. Eur J Pharmacol. 2007 Dec 1;575(1-3):94-7. PubMed PMID: 17727837. 5: Iijima M, Shimazaki T, Ito A, Chaki S. Effects of metabotropic glutamate 2/3 receptor antagonists in the stress-induced hyperthermia test in singly housed mice. Psychopharmacology (Berl). 2007 Feb;190(2):233-9. PubMed PMID: 17102982. 6: Karasawa J, Yoshimizu T, Chaki S. A metabotropic glutamate 2/3 receptor antagonist, MGS0039, increases extracellular dopamine levels in the nucleus accumbens shell. Neurosci Lett. 2006 Jan 30;393(2-3):127-30. PubMed PMID: 16233956. 7: Yoshimizu T, Shimazaki T, Ito A, Chaki S. An mGluR2/3 antagonist, MGS0039, exerts antidepressant and anxiolytic effects in behavioral models in rats. Psychopharmacology (Berl). 2006 Jul;186(4):587-93. PubMed PMID: 16612616. 8: Yasuhara A, Nakamura M, Sakagami K, Shimazaki T, Yoshikawa R, Chaki S, Ohta H, Nakazato A. Prodrugs of 3-(3,4-dichlorobenzyloxy)-2-amino-6-fluorobicyclo[3.1.0]hexane-2,6-dicarboxylic acid (MGS0039): a potent and orally active group II mGluR antagonist with antidepressant-like potential. Bioorg Med Chem. 2006 Jun 15;14(12):4193-207. PubMed PMID: 16487713. 9: Karasawa J, Shimazaki T, Kawashima N, Chaki S. AMPA receptor stimulation mediates the antidepressant-like effect of a group II metabotropic glutamate receptor antagonist. Brain Res. 2005 Apr 25;1042(1):92-8. PubMed PMID: 15823257. 10: Nakamura M, Kawakita Y, Yasuhara A, Fukasawa Y, Yoshida K, Sakagami K, Nakazato A. In vitro and in vivo evaluation of the metabolism and bioavailability of ester prodrugs of mgs0039 (3-(3,4-dichlorobenzyloxy)-2-amino-6-fluorobicyclo[3.1.0]hexane-2,6-dicarboxylic Acid), a potent metabotropic glutamate receptor antagonist. Drug Metab Dispos. 2006 Mar;34(3):369-74. PubMed PMID: 16326817. 11: Kawashima N, Karasawa J, Shimazaki T, Chaki S, Okuyama S, Yasuhara A, Nakazato A. Neuropharmacological profiles of antagonists of group II metabotropic glutamate receptors. Neurosci Lett. 2005 Apr 22;378(3):131-4. PubMed PMID: 15781145. 12: Chaki S, Yoshikawa R, Hirota S, Shimazaki T, Maeda M, Kawashima N, Yoshimizu T, Yasuhara A, Sakagami K, Okuyama S, Nakanishi S, Nakazato A. MGS0039: a potent and selective group II metabotropic glutamate receptor antagonist with antidepressant-like activity. Neuropharmacology. 2004 Mar;46(4):457-67. PubMed PMID: 14975669. 13: Shimazaki T, Iijima M, Chaki S. Anxiolytic-like activity of MGS0039, a potent group II metabotropic glutamate receptor antagonist, in a marble-burying behavior test. Eur J Pharmacol. 2004 Oct 6;501(1-3):121-5. PubMed PMID: 15464070. 14: Yoshimizu T, Chaki S. Increased cell proliferation in the adult mouse hippocampus following chronic administration of group II metabotropic glutamate receptor antagonist, MGS0039. Biochem Biophys Res Commun. 2004 Mar 5;315(2):493-6. PubMed PMID: 14766235.

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