(2R,3S)-E1R is an enantiomer of E1R (Compound 2c). (2R,3S)-E1R is a positive allosteric modulator (PAM) of sigma-1 receptor (Sig1R PAM) and may be utilized in the research/study of cognitive and memory disorders.

Physicochemical Properties

Molecular Formula	C13H16N2O2
Molecular Weight	232.278343200684
Exact Mass	232.121
CAS #	1424832-60-9
Related CAS #	E1R;1301211-78-8;(2S,3S)-E1R;1424832-57-4;(2R,3R)-E1R;1400888-63-2;(Rac)-E1R;787623-60-3
PubChem CID	71659350
Appearance	Light yellow to yellow solid powder
LogP	0.6
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	2
Rotatable Bond Count	3
Heavy Atom Count	17
Complexity	311
Defined Atom Stereocenter Count	2
SMILES	O=C1C[C@@H](C2C=CC=CC=2)[C@@H](C)N1CC(N)=O
InChi Key	ZTGRWYMPQCQTHD-MWLCHTKSSA-N
InChi Code	InChI=1S/C13H16N2O2/c1-9-11(10-5-3-2-4-6-10)7-13(17)15(9)8-12(14)16/h2-6,9,11H,7-8H2,1H3,(H2,14,16)/t9-,11-/m1/s1
Chemical Name	2-[(2R,3S)-2-methyl-5-oxo-3-phenylpyrrolidin-1-yl]acetamide
HS Tariff Code	2934.99.9001
Storage	Powder-20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month
Shipping Condition	Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)

Biological Activity

ln Vitro	Neuronal plasticity is a process linked to the pathophysiology of neuropsychiatric illnesses such schizophrenia, severe depression, and Alzheimer's disease [1]. Sigma-1 receptors are crucial players in this process.
References	[1]. Synthesis and biological evaluation of 2-(5-methyl-4-phenyl-2-oxopyrrolidin-1-yl)-acetamide stereoisomers as novel positive allosteric modulators of sigma-1 receptor. Bioorg Med Chem. 2013 May 15;21(10):2764-71.

Solubility Data

Solubility (In Vitro)

DMSO : ~250 mg/mL (~1076.29 mM)

Solubility (In Vivo)

Solubility in Formulation 1: ≥ 12.5 mg/mL (53.81 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 125.0 mg/mL clear DMSO stock solution to 400 μL of PEG300 and mix evenly; then add 50 μL of Tween-80 to the above solution and mix evenly; then add 450 μL of normal saline to adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 2: ≥ 12.5 mg/mL (53.81 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 125.0 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly. Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. Solubility in Formulation 3: ≥ 12.5 mg/mL (53.81 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 125.0 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly.  (Please use freshly prepared in vivo formulations for optimal results.)

Preparing Stock Solutions		1 mg	5 mg	10 mg
	1 mM	4.3051 mL	21.5257 mL	43.0515 mL
	5 mM	0.8610 mL	4.3051 mL	8.6103 mL
	10 mM	0.4305 mL	2.1526 mL	4.3051 mL

*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.