Methylphenylpiracetam
Chemical compound
From Wikipedia, the free encyclopedia
Methylphenylpiracetam is a derivative of piracetam and a positive allosteric modulator of the sigma-1 receptor.[1][2][3] It differs from phenylpiracetam by having a methyl group.[2]
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| Names | |
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| IUPAC name
2-(5-Methyl-2-oxo-4-phenyl-pyrrolidin-1-yl)-acetamide | |
| Identifiers | |
3D model (JSmol) |
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| ChEMBL | |
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PubChem CID |
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CompTox Dashboard (EPA) |
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| Properties | |
| 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).
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E1R is the (4R,5S) stereoisomer of methylphenylpiracetam that has been shown to have the greatest effect on the modulation of the sigma-1 receptor.[2]
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).[1][3]
| Enantiomer | σ1R PAM effect %[3] |
|---|---|
| erythro-(4R,5S) | 222 ± 37 |
| threo-(4R,5R) | 191 ± 23 |
| erythro-(4S,5R) | 141 ± 40 |
| threo-(4S,5S) | 147 ± 31 |
Effects
E1R enhances cognition and has efficacy against cholinergic dysfunction in mice without affecting locomotor activity.[2] Pretreatment with E1R enhanced the σ1R agonist PRE-084's stimulating effect and facilitated passive avoidance retention.[2] It alleviated scopolamine-induced cognitive impairment.[2] The cognition enhancing activity of E1R is higher than that of (R)-phenylpiracetam.[4]
Because E1R had no effect on locomotor activity, it was found to be free of potential motor side effects.[2]
Legality
Australia
Methylphenylpiracetam is a schedule 4 substance in Australia under the Poisons Standard (February 2020).[5] 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."[5]