Methylphenylpiracetam

Methylphenylpiracetam

Names
IUPAC name 2-(5-Methyl-2-oxo-4-phenyl-pyrrolidin-1-yl)-acetamide
Identifiers
CAS Number	1301211-78-8 N[ChemSpider]
3D model (JSmol)	Interactive image
ChEMBL	ChEMBL2391147
ChemSpider	30831670
PubChem CID	52912210
InChI 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-/m0/s1 Key: ZTGRWYMPQCQTHD-ONGXEEELSA-N
SMILES C[C@H]1[C@H](CC(=O)N1CC(=O)N)C2=CC=CC=C2
Properties
Chemical formula	C13H16N2O2
Molar mass	232.283 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.

Enantiomers

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).

Effects

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.

Legality

Australia

Methylphenylpiracetam is a schedule 4 substance in Australia under the Poisons Standard (February 2020). A schedule 4 substance is classified as "Prescription Only Medicine, or Prescription Animal Remedy – Substances, the use or supply of which should be by or on the order of persons permitted by State or Territory legislation to prescribe and should be available from a pharmacist on prescription."

See also

• Diastereomer

External links

• Screening profile of 10 μM E1R in vitro binding assays (docx)

Further reading

• US patent 8791273, Kalvins, et al., "4R,5S-enantiomer of 2-(5-methyl-2-oxo-4-phenyl-pyrrolidin-1-yl)-acetamide with nootropic activity", issued 2014-07-29