MedKoo Cat#: 462373 | Name: EU-1180-453

Description:

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

R-(+)-EU-1180-453 is a second-generation GluN2C/D-selective NMDAR-positive allosteric modulators (PAMs). It exhibits log unit improvements in the concentration needed to double receptor response, lipophilic efficiency, and aqueous solubility, and lowers cLogP by one log unit compared to the first-generation prototype CIQ. Additionally, R-(+)-EU-1180-453 was found to increase glutamate potency 2-fold, increase the response to maximally effective concentration of agonist 4-fold, and the racemate is brain-penetrant.

Chemical Structure

EU-1180-453
EU-1180-453
CAS#2488764-06-1 (R-isomer)

Theoretical Analysis

MedKoo Cat#: 462373

Name: EU-1180-453

CAS#: 2488764-06-1 (R-isomer)

Chemical Formula: 380.1536

Exact Mass: 380.1536

Molecular Weight: 380.42

Elemental Analysis: C, 69.46; H, 5.56; F, 4.99; N, 7.36; O, 12.62

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 #
2409691-90-1 (racemic) 2488764-06-1 (R-isomer)
Synonym
R-(+)-EU-1180-453; R-(+)-EU 1180-453; R-(+)-EU1180-453; EU-1180-453; EU 1180-453; EU1180-453; EU-1180453; EU 1180453; EU1180453;
IUPAC/Chemical Name
(R)-2-(3-Fluorobenzyl)-1-((4-methoxyphenoxy)methyl)-1,2-dihydropyrrolo[1,2-a]pyrazin-3(4H)-one
InChi Key
AQEMZTCFTYISLD-NRFANRHFSA-N
InChi Code
InChI=1S/C22H21FN2O3/c1-27-18-7-9-19(10-8-18)28-15-21-20-6-3-11-24(20)14-22(26)25(21)13-16-4-2-5-17(23)12-16/h2-12,21H,13-15H2,1H3/t21-/m0/s1
SMILES Code
O=C1N(CC2=CC=CC(F)=C2)[C@@H](COC3=CC=C(OC)C=C3)C4=CC=CN4C1
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

Preparing Stock Solutions

The following data is based on the product molecular weight 380.42 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: Epplin MP, Mohan A, Harris LD, et al. Discovery of Dihydropyrrolo[1,2-a]pyrazin-3(4H)-one-Based Second-Generation GluN2C- and GluN2D-Selective Positive Allosteric Modulators (PAMs) of the N-Methyl-d-Aspartate (NMDA) Receptor. Journal of Medicinal Chemistry. 2020 Jul. DOI: 10.1021/acs.jmedchem.9b01733.