Aniracetam (brand names Draganon, Sarpul, Ampamet, Memodrin, Referan), also known as ''N''-anisoyl-2-pyrrolidinone, is a racetam which is sold in

Europe Europe is a large peninsula conventionally considered a continent in its own right because of its great physical size and the weight of its history and traditions. Europe is also considered a Continent#Subcontinents, subcontinent of Eurasia ...

as a prescription drug. It is not approved by the

Food and Drug Administration The United States Food and Drug Administration (FDA or US FDA) is a federal agency of the Department of Health and Human Services. The FDA is responsible for protecting and promoting public health through the control and supervision of food ...

for use in the

United States The United States of America (U.S.A. or USA), commonly known as the United States (U.S. or US) or America, is a country Continental United States, primarily located in North America. It consists of 50 U.S. state, states, a Washington, D.C., ...

as a prescription medication or

dietary supplement A dietary supplement is a manufactured product intended to supplement one's diet by taking a pill, capsule, tablet, powder, or liquid. A supplement can provide nutrients either extracted from food sources or that are synthetic in order ...

. Despite the FDA's lack of approval, the drug is readily available over-the-counter in the US as a dietary supplement.

Pharmacology

Aniracetam has been shown to positively modulate the

AMPA receptor The α-amino-3-hydroxy-5-methyl-4-isoxazolepropionic acid receptor (also known as AMPA receptor, AMPAR, or quisqualate receptor) is an ionotropic transmembrane receptor for glutamate ( iGluR) that mediates fast synaptic transmission in the cent ...

. 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%). Plasma concentrations are generally in the 5–15 ''μ''g/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.

Synthesis

The drug was first made in the 1970s by

Hoffmann-La Roche F. Hoffmann-La Roche AG, commonly known as Roche, is a Swiss multinational healthcare company that operates worldwide under two divisions: Pharmaceuticals and Diagnostics. Its holding company, Roche Holding AG, has shares listed on the SIX ...

. Synthesis can be accomplished by reacting 2-pyrrolidone with anisoyl chloride in the presence of

triethylamine Triethylamine is the chemical compound with the formula N(CH2CH3)3, commonly abbreviated Et3N. It is also abbreviated TEA, yet this abbreviation must be used carefully to avoid confusion with triethanolamine or tetraethylammonium, for which TEA ...

. Alternatively, gamma-aminobutyric acid can react with anisoyl chloride. Ring closure can be accomplished in the presence of thionyl chloride.

Legality

Australia

Aniracetam 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

{{Racetams AMPA receptor positive allosteric modulators Nootropics Phenol ethers Racetams

Pharmacology

Synthesis

Legality

Australia

See also

References