Aniracetam

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Aniracetam (brand names Draganon, Sarpul, Ampamet, Memodrin, Referan), also known as N-anisoyl-2-pyrrolidinone, is a racetam which is sold in Europe as a prescription drug. It is not approved by the Food and Drug Administration for use in the United States as a prescription medication or dietary supplement.<ref name="Neuro">Template:Cite journal</ref><ref>Template:Cite journal</ref> Despite the FDA's lack of approval, the drug is readily available over-the-counter in misbranded dietary supplements.<ref name="Neuro"/>

Medical uses

Aniracetam has been used to treat dementia following stroke and in Alzheimer's disease.<ref>Template:Cite journal</ref> Results from human clinical trials were published in 1991 (one multi-center placebo-controlled study and a follow-up) and in 2011 (one open-label study).<ref>Template:Cite journal – Part used: references section.</ref>

It has undergone a larger number of experiments in rodents; in a 1982 experiment on rats and mice it was found to have a variety of psychoactive effects, improving learning and memory that was otherwise impaired experimentally.<ref>Template:Cite journal</ref> It has been identified as a nootropic drug due to these memory effects.<ref>Template:Cite journal</ref> A 2001 study reported that in mice it has modest effects similar to an anxiolytic.<ref>Template:Cite journal</ref>

Pharmacology

Aniracetam has been shown to positively modulate the AMPA receptor.<ref>Template:Cite journal</ref>

When ingested orally aniracetam is quickly broken down via first pass hepatic metabolism. The primary metabolites of aniracetam are N-anisoyl-GABA, (70–80%), 2-Pyrrolidinone and p-anisic acid (20–30%).<ref name ="lee">Template:Cite journal</ref><ref>Template:Cite book</ref><ref name="TestaMayer2003">Template:Cite book</ref> There is some preliminary research suggesting that N-anisoyl-GABA and to a lesser degree p-ansic acid may contribute to the stimulatory effects of aniracetam in rats.<ref name="ratsdepression"/> Further work in rats suggests that N-anisoyl-GABA may contribute more to increasing acetylcholine release than aniracetam itself.<ref>Template:Cite journal</ref> For instance, a study using the forced swim test in rats found that the two metabolites 2-pyrrolidinone and N-anisoyl-GABA alone yielded similar anti-depressant effects as aniracetam itself.<ref name="ratsdepression">Template:Cite journal</ref> The authors of the aforementioned study hypothesized that the metabolites work by increasing levels of dopamine and by stimulating the nicotinic acetylcholine receptors.<ref name="ratsdepression"/>

Plasma concentrations are generally in the 5–15 μg/L range for aniracetam and 5–15 mg/L range for N-anisoyl-GABA, a pharmacologically active metabolite, during the first few hours after oral administration of the drug. These two plasma species may be measured by liquid chromatography-mass spectrometry.<ref name="Cai_2012">Template:Cite journal</ref><ref>Template:Cite journal</ref><ref>Template:Cite book</ref>

Synthesis

The drug was first made in the 1970s by Hoffmann-La Roche.<ref>Template:Cite patent</ref><ref>Template:Cite patent</ref> Synthesis can be accomplished by reacting 2-pyrrolidone with anisoyl chloride in the presence of triethylamine.<ref name="Kleemann">Template:Cite book</ref>

Alternatively, gamma-aminobutyric acid can react with anisoyl chloride. Ring closure can be accomplished in the presence of thionyl chloride.<ref name="Kleemann"/>

Legality

Europe

Aniracetam is available by prescription in Greece (brand names Memodrin and Referan) and Italy (brand name Ampamet), where it is indicated for mental function disorders.<ref name="nz_medsafe">{{#invoke:citation/CS1|citation |CitationClass=web }}</ref>

Australia

Aniracetam is a schedule 4 substance in Australia under the Poisons Standard (February 2020).<ref name="Poisons Stanrard">Poisons Standard February 2020. comlaw.gov.au</ref> 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."<ref name="Poisons Stanrard" />

See also

• AMPA receptor positive allosteric modulator