Methylphenylpiracetam

Methylphenylpiracetam
Names

IUPAC name 2-(5-Methyl-2-oxo-4-phenyl-pyrrolidin-1-yl)-acetamide
Identifiers
3D model (JSmol)	Interactive image
PubChem CID	52912210
SMILES C[C@H]1[C@H](CC(=O)N1CC(=O)N)C2=CC=CC=C2
Properties
Chemical formula	C₁₃H₁₆N₂O₂
Molar mass	232.28 g·mol⁻¹
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Methylphenylpiracetam is a derivative of piracetam and a positive allosteric modulator of the sigma-1 receptor. It differs from phenylpiracetam by having a methyl group.

E1R is the (4R,5S) stereoisomer of methylphenylpiracetam.

The two R-configuration enantiomers, i.e. (4R,5S) and (4R,5R), of methylphenylpiracetam are more active positive allosteric modulators of the sigma-1 receptor than the two S-configuration enantiomers, i.e. (4S,5R) and (4S,5S).

E1R enhances cognition and has efficacy against cholinergic dysfunction in mice without affecting locomotor activity. Pretreatment with E1R enhanced the σ₁R agonist PRE-084's stimulating effect and facilitated passive avoidance retention. It alleviated scopolamine-induced cognitive impairment. The cognition enhancing activity of E1R is higher than that of (R)-phenylpiracetam.

Because E1R had no effect on locomotor activity, it was found to be free of potential motor side effects.

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