Cannabaceae

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Methylphenylpiracetam
Names
IUPAC name
2-(5-Methyl-2-oxo-4-phenyl-pyrrolidin-1-yl)-acetamide
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
  • 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
  • C[C@H]1[C@H](CC(=O)N1CC(=O)N)C2=CC=CC=C2
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).

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[edit]

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[edit]

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[edit]

Australia[edit]

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]

See also[edit]

References[edit]

  1. ^ a b Vavers E, Zvejniece L, Veinberg G, Svalbe B, Domracheva I, Vilskersts R, Dambrova M (2015). "Novel positive allosteric modulators of sigma-1 receptor". SpringerPlus. 4 (Suppl 1): P51. doi:10.1186/2193-1801-4-S1-P51. PMC 4797911. The R-configuration enantiomers of methylphenylpiracetam are more active positive allosteric modulators of Sigma-1 receptor than S-configuration enantiomers.
  2. ^ a b c d e f g Zvejniece, L; Vavers, E; Svalbe, B; Vilskersts, R; Domracheva, I; Vorona, M; Veinberg, G; Misane, I; Stonans, I; Kalvinsh, I; Dambrova, M (2014). "The cognition-enhancing activity of E1R, a novel positive allosteric modulator of sigma-1 receptors". British Journal of Pharmacology. 171 (3): 761–71. doi:10.1111/bph.12506. PMC 3969087. PMID 24490863.
  3. ^ a b c Veinberg, G; 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 (2013). "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. doi:10.1016/j.bmc.2013.03.016. PMID 23582449.
  4. ^ Veinberg G, Vavers E, Orlova N, Kuznecovs J, Domracheva I, Vorona M, Zvejniece L, Dambrova M (2015). "Stereochemistry of phenylpiracetam and its methyl derivative: improvement of the pharmacological profile". Chemistry of Heterocyclic Compounds. 51 (7): 601–606. doi:10.1007/s10593-015-1747-9. S2CID 93449199. 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.
  5. ^ a b Poisons Standard February 2020. comlaw.gov.au

External links[edit]

Further reading[edit]

source: https://en.wikipedia.org/wiki/Methylphenylpiracetam

One thought on “Cannabaceae”

  1. Well, that’s interesting to know that Psilotum nudum are known as whisk ferns. Psilotum nudum is the commoner species of the two. While the P. flaccidum is a rare species and is found in the tropical islands. Both the species are usually epiphytic in habit and grow upon tree ferns. These species may also be terrestrial and grow in humus or in the crevices of the rocks.
    View the detailed Guide of Psilotum nudum: Detailed Study Of Psilotum Nudum (Whisk Fern), Classification, Anatomy, Reproduction

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