Aniracetam

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Medication

title: "Aniracetam" type: doc version: 1 created: 2026-02-28 author: "Wikipedia contributors" status: active scope: public tags: ["ampa-receptor-positive-allosteric-modulators", "nootropics", "4-methoxyphenyl-compounds", "racetams"] description: "Medication" topic_path: "general/ampa-receptor-positive-allosteric-modulators" source: "https://en.wikipedia.org/wiki/Aniracetam" license: "CC BY-SA 4.0" wikipedia_page_id: 0 wikipedia_revision_id: 0

::summary Medication ::

::data[format=table title="Infobox drug"]

FieldValue
Verifiedfieldschanged
Watchedfieldschanged
verifiedrevid477164594
IUPAC_name1-[(4-Methoxybenzoyl)]-2-pyrrolidinone
imageAniracetam.svg
image_classskin-invert-image
width200
image2Aniracetam3d.png
image_class2bg-transparent
width2175
tradename
Drugs.com
legal_US_commentUnapproved "New Drug" (as defined by 21 U.S. Code § 321(p)(1)). Use in dietary supplements, food, or medicine is unlawful; otherwise uncontrolled.
legal_AUS4
routes_of_administrationBy mouth
elimination_half-life0.5 hours
excretion
IUPHAR_ligand4133
CAS_number_Ref
CAS_number72432-10-1
ATC_prefixN06
ATC_suffixBX11
PubChem2196
DrugBank_Ref
DrugBankDB04599
ChemSpiderID_Ref
ChemSpiderID2111
UNII_Ref
UNII5L16LKN964
KEGG_Ref
KEGGD01883
ChEBI_Ref
ChEBI47943
ChEMBL_Ref
ChEMBL36994
C
H13
N1
O3
smilesO=C2N(C(=O)c1ccc(OC)cc1)CCC2
StdInChI_Ref
StdInChI1S/C12H13NO3/c1-16-10-6-4-9(5-7-10)12(15)13-8-2-3-11(13)14/h4-7H,2-3,8H2,1H3
StdInChIKey_Ref
StdInChIKeyZXNRTKGTQJPIJK-UHFFFAOYSA-N
::

| Verifiedfields = changed | Watchedfields = changed | verifiedrevid = 477164594 | IUPAC_name = 1-[(4-Methoxybenzoyl)]-2-pyrrolidinone | image = Aniracetam.svg | image_class = skin-invert-image | width = 200 | image2 = Aniracetam3d.png | image_class2 = bg-transparent | width2 = 175

| tradename = Ampamet, Memodrin, Pergamid | Drugs.com = | pregnancy_category = | legal_US_comment = Unapproved "New Drug" (as defined by 21 U.S. Code § 321(p)(1)). Use in dietary supplements, food, or medicine is unlawful; otherwise uncontrolled. | legal_AU = S4 | legal_status = | routes_of_administration = By mouth

| bioavailability = | metabolism = | elimination_half-life = 0.5 hours | excretion = | IUPHAR_ligand = 4133 | CAS_number_Ref = | CAS_number = 72432-10-1 | ATC_prefix = N06 | ATC_suffix = BX11 | PubChem = 2196 | DrugBank_Ref = | DrugBank = DB04599 | ChemSpiderID_Ref = | ChemSpiderID = 2111 | UNII_Ref = | UNII = 5L16LKN964 | KEGG_Ref = | KEGG = D01883 | ChEBI_Ref = | ChEBI = 47943 | ChEMBL_Ref = | ChEMBL = 36994

| C = 12 | H = 13 | N = 1 | O = 3 | smiles = O=C2N(C(=O)c1ccc(OC)cc1)CCC2 | StdInChI_Ref = | StdInChI = 1S/C12H13NO3/c1-16-10-6-4-9(5-7-10)12(15)13-8-2-3-11(13)14/h4-7H,2-3,8H2,1H3 | StdInChIKey_Ref = | StdInChIKey = ZXNRTKGTQJPIJK-UHFFFAOYSA-N

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. Despite the FDA's lack of approval, the drug is readily available over-the-counter in misbranded dietary supplements.

Medical uses

Aniracetam has been used to treat dementia following stroke and in Alzheimer's disease. 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).

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. It has been identified as a nootropic drug due to these memory effects. A 2001 study reported that in mice it has modest effects similar to an anxiolytic.

Pharmacology

Aniracetam has been shown to positively modulate the AMPA receptor.

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%). 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. Further work in rats suggests that N-anisoyl-GABA may contribute more to increasing acetylcholine release than aniracetam itself. 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. The authors of the aforementioned study hypothesized that the metabolites work by increasing levels of dopamine and by stimulating the nicotinic acetylcholine receptors.

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.

Synthesis

The drug was first made in the 1970s by Hoffmann-La Roche. Synthesis can be accomplished by reacting 2-pyrrolidone with anisoyl chloride in the presence of triethylamine.

::figure[src="https://upload.wikimedia.org/wikipedia/commons/a/a8/Aniracetam_synthesis_01.svg"] ::

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

::figure[src="https://upload.wikimedia.org/wikipedia/commons/1/10/Aniracetam_synthesis_02.svg"] ::

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.

Australia

Aniracetam is a schedule 4 substance 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

References

  1. (June 1993). "Human Pharmacokinetics of Aniracetam". Drug Investigation.
  2. (February 2010). "Piracetam and piracetam-like drugs: from basic science to novel clinical applications to CNS disorders". Drugs.
  3. (June 2021). "Five Unapproved Drugs Found in Cognitive Enhancement Supplements". Neurology. Clinical Practice.
  4. (March 2002). "Aniracetam: its novel therapeutic potential in cerebral dysfunctional disorders based on recent pharmacological discoveries". CNS Drug Reviews.
  5. (2024). "Aniracetam: An Evidence-Based Model for Preventing the Accumulation of Amyloid-β Plaques in Alzheimer's Disease.". Journal of Alzheimer's Disease.
  6. (October 1982). "Effects of the novel compound aniracetam (Ro 13-5057) upon impaired learning and memory in rodents". Psychopharmacology.
  7. (December 1991). "Aniracetam reduces glutamate receptor desensitization and slows the decay of fast excitatory synaptic currents in the hippocampus". Proceedings of the National Academy of Sciences of the United States of America.
  8. (May 2001). "Anxiolytic effects of aniracetam in three different mouse models of anxiety and the underlying mechanism". European Journal of Pharmacology.
  9. (May 1990). "Allosteric potentiation of quisqualate receptors by a nootropic drug aniracetam". The Journal of Physiology.
  10. (March 1994). "Aniracetam. An overview of its pharmacodynamic and pharmacokinetic properties, and a review of its therapeutic potential in senile cognitive disorders". Drugs & Aging.
  11. (22 July 2013). "Schizophrenia: New Insights for the Healthcare Professional". ScholarlyEditions.
  12. (1 August 2003). "Hydrolysis in Drug and Prodrug Metabolism". John Wiley & Sons.
  13. (March 2000). "Group II metabotropic glutamate receptors are a common target of N-anisoyl-GABA and 1S,3R-ACPD in enhancing ACh release in the prefrontal cortex of freely moving SHRSP". Neuropharmacology.
  14. (November 2001). "Antidepressant-like effects of aniracetam in aged rats and its mode of action". Psychopharmacology.
  15. (May 2012). "Determination of aniracetam's main metabolite, N-anisoyl-GABA, in human plasma by LC-MS/MS and its application to a pharmacokinetic study". Journal of Chromatography B.
  16. (October 2007). "Sensitive and selective liquid chromatography-tandem mass spectrometry method for the quantification of aniracetam in human plasma". Journal of Chromatography B.
  17. (2014). "Disposition of Toxic Drugs and Chemicals in Man". Biomedical Publications.
  18. "p-Methoxy-benzoyl derivatives".
  19. "1-Benzoyl-2-pyrrolidinone derivative, processes for its preparation and medicaments containing it.".
  20. (2001). "Pharmaceutical substances: syntheses, patents, applications". Thieme.
  21. "Classification Status of Racetams". New Zealand Medicines and Medical Devices Safety Authority.
  22. [https://www.legislation.gov.au/Details/F2020C00148 Poisons Standard February 2020]. comlaw.gov.au

::callout[type=info title="Wikipedia Source"] This article was imported from Wikipedia and is available under the Creative Commons Attribution-ShareAlike 4.0 License. Content has been adapted to SurfDoc format. Original contributors can be found on the article history page. ::

ampa-receptor-positive-allosteric-modulatorsnootropics4-methoxyphenyl-compoundsracetams