Methylphenylpiracetam is a

derivative In mathematics, the derivative of a function of a real variable measures the sensitivity to change of the function value (output value) with respect to a change in its argument (input value). Derivatives are a fundamental tool of calculus. ...

of piracetam and a positive allosteric modulator of the

sigma-1 receptor The sigma-1 receptor (σ1R), one of two sigma receptor subtypes, is a chaperone protein at the endoplasmic reticulum (ER) that modulates calcium signaling through the IP3 receptor. In humans, the σ1 receptor is encoded by the ''SIGMAR1'' gen ...

. It differs from

phenylpiracetam Phenylpiracetam ( INN: fonturacetam, brand names Phenotropil Фенотропил, Carphedon), is a phenylated analog of the drug piracetam. It was developed in 1983 as a medication for Soviet Cosmonauts to treat the prolonged stresses of wor ...

by having a

methyl group In organic chemistry, a methyl group is an alkyl derived from methane, containing one carbon atom bonded to three hydrogen atoms, having chemical formula . In formulas, the group is often abbreviated as Me. This hydrocarbon group occurs in ma ...

. E1R is the (4''R'',5''S'')

stereoisomer In stereochemistry, stereoisomerism, or spatial isomerism, is a form of isomerism in which molecules have the same molecular formula and sequence of bonded atoms (constitution), but differ in the three-dimensional orientations of their atoms in ...

of methylphenylpiracetam.

Enantiomers

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

Effects

E1R enhances cognition and has efficacy against

cholinergic Cholinergic agents are compounds which mimic the action of acetylcholine and/or butyrylcholine. In general, the word " choline" describes the various quaternary ammonium salts containing the ''N'',''N'',''N''-trimethylethanolammonium cati ...

dysfunction in mice without affecting

locomotor activity Animal locomotion, in ethology, is any of a variety of methods that animals use to move from one place to another. Some modes of locomotion are (initially) self-propelled, e.g., running, swimming, jumping, flying, hopping, soaring and gliding. Th ...

. Pretreatment with E1R enhanced the σ₁R agonist

PRE-084 PRE-084 is a sigma receptor agonist, selective for the σ1 subtype. It has nootropic and antidepressant actions in animal studies, as well as antitussive and reinforcing effects. PRE-084 increases the expression of GDNF Glial cell line-deri ...

's stimulating effect and facilitated

passive avoidance Passive may refer to: * Passive voice, a grammatical voice common in many languages, see also Pseudopassive * Passive language, a language from which an interpreter works * Passivity (behavior), the condition of submitting to the influence of on ...

retention. It alleviated scopolamine-induced

cognitive impairment Cognitive deficit is an inclusive term to describe any characteristic that acts as a barrier to the cognition process. The term may describe * deficits in overall intelligence (as with intellectual disabilities), * specific and restricted defici ...

. 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).Poisons Standard February 2020
comlaw.gov.au 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."

References

External links

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