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 σ
1R 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](_blank)
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."
See also
*
Diastereomer
In stereochemistry, diastereomers (sometimes called diastereoisomers) are a type of stereoisomer. Diastereomers are defined as non-mirror image, non-identical stereoisomers. Hence, they occur when two or more stereoisomers of a compound have di ...
References
External links
Screening profile of 10 μM E1R in vitro binding assays(docx)
Further reading
*
{{Racetams
Racetams
Receptor modulators