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|Trade names||Ampamet, Memodrin, Pergamid|
|AHFS/Drugs.com||International Drug Names|
|Biological half-life||1–2.5 hours|
|Chemical and physical data|
|Molar mass||219.237 g/mol|
|3D model (Jmol)|
|(what is this?)|
Aniracetam (Draganon, Sarpul, Ampamet, Memodrin, Referan), also known as N-anisoyl-2-pyrrolidinone, is an ampakine nootropic of the racetam chemical class purported to be considerably more potent than piracetam. It is lipid-soluble and has possible cognition-enhancing effects. It has been tested in animals extensively, Alzheimer's patients, and temporarily impaired healthy subjects. It has shown potential as an anxiolytic in three clinical animal models. It is sold in Europe as a prescription drug, but it is not approved by the Food and Drug Administration for use in the United States.
Aniracetam has also been shown to positively modulate the AMPA receptor and was used as the parent compound to derive a class of drugs known as the ampakines that are being investigated as nootropics and neuroprotective drugs for the treatment of Alzheimer's disease and other neurodegenerative conditions.
After a confirmed test of the anxiolytic efficacy in a mouse model, haloperidol, mecamylamine, and ketanserin were applied to determine the pathways aniracetam depends on to exert its anti-anxiety effects. Haloperidol completely reversed the anxiolytic effects, and mecamylamine and ketanserin nearly completely reversed the effects. These respectively suggest that aniracetam's anxiolytic mechanism may be mediated through D2, nAChR, and/or 5-HT2A receptor activity.
The main metabolite of aniracetam (70–80%), N-anisoyl-GABA, reproduces many of the effects of aniracetam. 2-Pyrrolidinone and p-anisic acid are additional metabolites of the drug (20–30%), both of which are also active.
The drug was first made in the 1970s by Hoffmann-La Roche.[full citation needed][full citation needed] Synthesis can be accomplished by reacting 2-pyrrolidone with anisoyl chloride in the presence of triethylamine.
When ingested orally aniracetam is quickly broken down via first pass hepatic metabolism. The primary metabolites of aniracetam are N-anisoyl-GABA, 2-pyrrolidone, and anisic acid. 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.
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