Methylphenylpiracetam Explained
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]
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 % |
|---|
| 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."
See also
External links
Notes and References
- 2015 . Novel positive allosteric modulators of sigma-1 receptor . Vavers E, Zvejniece L, Veinberg G, Svalbe B, Domracheva I, Vilskersts R, Dambrova M . 10.1186/2193-1801-4-S1-P51 . The R-configuration enantiomers of methylphenylpiracetam are more active positive allosteric modulators of Sigma-1 receptor than S-configuration enantiomers. . 4 . Suppl 1 . SpringerPlus . P51. 4797911 . free .
- 24490863. 3969087. 2014. Zvejniece. L. The cognition-enhancing activity of E1R, a novel positive allosteric modulator of sigma-1 receptors. British Journal of Pharmacology. 171. 3. 761–71. Vavers. E. Svalbe. B. Vilskersts. R. Domracheva. I. Vorona. M. Veinberg. G. Misane. I. Stonans. I. Kalvinsh. I. Dambrova. M. 10.1111/bph.12506.
- 23582449. 2013. Veinberg. G. 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. Bioorganic & Medicinal Chemistry. 21. 10. 2764–71. Vorona. M. Zvejniece. L. Vilskersts. R. Vavers. E. Liepinsh. E. Kazoka. H. Belyakov. S. Mishnev. A. Kuznecovs. J. Vikainis. S. Orlova. N. Lebedev. A. Ponomaryov. Y. Dambrova. M. 10.1016/j.bmc.2013.03.016.
- 2015 . 51 . 7 . 601–606 . Veinberg G, Vavers E, Orlova N, Kuznecovs J, Domracheva I, Vorona M, Zvejniece L, Dambrova M . Stereochemistry of phenylpiracetam and its methyl derivative: improvement of the pharmacological profile . Chemistry of Heterocyclic Compounds . In conclusion, the obtained data demonstrated that E1R is the most active memory enhancing enantiomer of the 5-methyl-substituted phenylpiracetam homolog, and its cognition enhancing activity is higher than that of (R)-phenylpiracetam. . 10.1007/s10593-015-1747-9. 93449199 .
- https://www.legislation.gov.au/Details/F2020C00148 Poisons Standard February 2020
