Racetam

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Class of drugs

title: "Racetam" type: doc version: 1 created: 2026-02-28 author: "Wikipedia contributors" status: active scope: public tags: ["racetams", "chemical-classes-of-psychoactive-drugs", "drugs-with-unknown-mechanisms-of-action"] description: "Class of drugs" topic_path: "general/racetams" source: "https://en.wikipedia.org/wiki/Racetam" license: "CC BY-SA 4.0" wikipedia_page_id: 0 wikipedia_revision_id: 0

::summary Class of drugs ::

::figure[src="https://upload.wikimedia.org/wikipedia/commons/4/45/2-Pyrrolidone.png" caption="[[2-Pyrrolidone"] ::

::figure[src="https://upload.wikimedia.org/wikipedia/commons/e/e9/Piracetam.svg" caption="[[Piracetam"] ::

Racetams, also sometimes known simply as pyrrolidones, are a class of drugs that share a pyrrolidone nucleus. Many, but not all, specifically have a 2-oxo-1-pyrrolidine acetamide (piracetam) nucleus. Some racetams, such as piracetam, aniracetam, oxiracetam, pramiracetam, and phenylpiracetam, are considered nootropics. Phenylpiracetam is also a stimulant. Others, such as levetiracetam, brivaracetam, and seletracetam, are anticonvulsants.

Mechanism

There is no universally accepted mechanism of action for racetams. Racetams generally show negligible affinity for common central nervous system receptors, but modulation of central neurotransmitters, including acetylcholine and glutamate, has been reported. Although aniracetam and nebracetam show some affinity for muscarinic acetylcholine receptors, only nefiracetam demonstrates nanomolar interactions with neurotransmitter receptors. Modification of membrane-located mechanisms of central signal transduction is another hypothesis.

Like some ampakines, some racetams, such as piracetam and aniracetam, are positive allosteric modulators of the AMPA receptor.

Racetams are understood to work by allosterically modulating glutamate receptors, specifically AMPA receptors, leading to Ca2+ influx that is excitatory. Racetams are posited to enhance memory through interaction with glutamate receptors in the central nervous system.

Phenylpiracetam, unique among racetams in being a phenethylamine and stimulant, is an atypical dopamine reuptake inhibitor.

Anticonvulsant racetams, including levetiracetam, brivaracetam, and seletracetam, act as synaptic vesicle glycoprotein 2A (SV2A) ligands. A newer analogue of these agents, padsevonil, is no longer a racetam itself but is much more potent in comparison and interacts with not only SV2A but also synaptic vesicle glycoprotein 2B (SV2B) and synaptic vesicle glycoprotein 2C (SV2C).

Methylphenylpiracetam, a derivative of phenylpiracetam, is a positive allosteric modulator of the sigma σ1 receptor. It is currently the only racetam known to possess this action.

Cofactors

In studies with aged rats, marked improvement has been observed in cognitive tasks in experimental groups given piracetam. Performance was further increased when piracetam was combined with choline. Evidence in studies with rats has indicated that the potency of piracetam is increased when administered with choline.

List of racetams

::data[format=table]

Structure	Name
[[File:Piracetam.svg	125px
[[File:Oxiracetam.svg	125px
[[File:Phenylpiracetam.svg	125px
[[File:Fonturacetam_hydrazide.svg	125px
[[File:Aniracetam.svg	125px
[[File:Pramiracetam.svg	125px
[[File:Seletracetam.svg	125px
[[File:Levetiracetam.svg	125px
[[File:Coluracetam.svg	125px
[[File:Fasoracetam.svg	125px
[[File:Brivaracetam.svg	125px
[[File:Dimiracetam.svg	125px
[[File:E1R.svg	125px
[[File:Nebracetam.svg	125px
[[File:Nefiracetam.svg	125px
[[File:Noopept.svg	125px
[[File:Rolziracetam structure.svg	125px
[[File:Cebaracetam.svg	125px
::

Chemistry

Racetams are 2-pyrrolidone derivatives and may sometimes be referred to simply as pyrrolidones (2-oxopyrrolidines). Many, but not all, specifically have a 2-oxo-1-pyrrolidine acetamide nucleus, which is the chemical structure of piracetam.

Racetams are cyclic derivatives of the inhibitory neurotransmitter γ-aminobutyric acid (GABA). They are also structurally related to the endogenous cyclic amino acid pyroglutamic acid (pyroglutamate), a cyclic analogue of the endogenous excitatory neurotransmitter glutamic acid (glutamate).

Some agents included in the racetam family are not technically racetams themselves in terms of chemical structure and instead are closely related compounds. They may be referred to as "racetam-like". These agents include aloracetam, molracetam, omberacetam (noopept), padsevonil, and tenilsetam.

Society and culture

Legality

Australia

All racetams are schedule 4 substances in Australia under the Poisons Standard (February 2020). 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

(December 2001). "Pyrrolidone derivatives". Lancet.
(February 2010). "Piracetam and piracetam-like drugs: from basic science to novel clinical applications to CNS disorders". Drugs.
(2002). "Design and study of piracetam-like nootropics, controversial members of the problematic class of cognition-enhancing drugs". Current Pharmaceutical Design.
(May 1994). "Piracetam and other structurally related nootropics". Brain Res Brain Res Rev.
(25 November 2019). "Presence of Piracetam in Cognitive Enhancement Dietary Supplements". JAMA Internal Medicine.
(March 2010). "Piracetam defines a new binding site for allosteric modulators of alpha-amino-3-hydroxy-5-methyl-4-isoxazole-propionic acid (AMPA) receptors". Journal of Medicinal Chemistry.
(April 1992). "Nootropic drugs positively modulate alpha-amino-3-hydroxy-5-methyl-4-isoxazolepropionic acid-sensitive glutamate receptors in neuronal cultures". Journal of Neurochemistry.
(July 2016). "Treatments and compositions for attention deficit hyperactivity disorder: a patent review". Expert Opin Ther Pat.
(2015). "Stereochemistry of phenylpiracetam and its methyl derivative: improvement of the pharmacological profile". Chemistry of Heterocyclic Compounds.
(December 2014). "The dopamine reuptake inhibitor MRZ-9547 increases progressive ratio responding in rats". The International Journal of Neuropsychopharmacology.
(February 2019). "Animal models of fatigue in major depressive disorder". Physiology & Behavior.
(May 2024). "Development of SV2A Ligands for Epilepsy Treatment: A Review of Levetiracetam, Brivaracetam, and Padsevonil". Neurosci Bull.
(2019). "Allosteric Modulators of Sigma-1 Receptor: A Review". Front Pharmacol.
(February 2014). "The cognition-enhancing activity of E1R, a novel positive allosteric modulator of sigma-1 receptors". Br J Pharmacol.
(2015). "Novel positive allosteric modulators of sigma-1 receptor". SpringerPlus.
(1981). "Profound effects of combining choline and piracetam on memory enhancement and cholinergic function in aged rats". Neurobiology of Aging.
(2015). "Classification Status of Racetams". Medsafe.
"The use of stems in the selection of International Nonproprietary Names (INN) for pharmaceutical substances 2018".
[https://www.legislation.gov.au/Details/F2020C00148 Poisons Standard February 2020]. comlaw.gov.au

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