Aniracetam

Aniracetam
Systematic (IUPAC) name
1-[(4-methoxybenzoyl)]- 2-pyrrolidinone
Clinical data
Trade names Ampamet, Memodrin, Pergamid
AHFS/Drugs.com International Drug Names
  • Unscheduled
Oral
Pharmacokinetic data
Half-life 1-2.5 hours
Identifiers
72432-10-1 
N06BX11
PubChem CID 2196
DrugBank DB04599 Yes
ChemSpider 2111 Yes
UNII 5L16LKN964 Yes
KEGG D01883 Yes
ChEBI CHEBI:47943 Yes
ChEMBL CHEMBL36994 Yes
Chemical data
Formula C12H13NO3
219.237 g/mol
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Aniracetam (Draganon, Sarpul, Ampamet, Memodrin, Referan) 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,[1] but it is not approved by the Food and Drug Administration for use in the United States.

Pharmacology

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. This shows that aniracetam's anxiolytic mechanism is possibly mediated through D2, nACh, and 5-HT2A receptor activity.[2]

Aniracetam has also been shown to selectively modulate the AMPA receptor[3] 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.[4]

Synthesis

The drug was first made in the 1970s by Hoffmann-La Roche.[5][6] Synthesis can be accomplished by reacting 2-pyrrolidone with anisoyl chloride in the presence of triethylamine.[7]

Alternatively, gamma-aminobutyric acid can react with anisoyl chloride. Ring closure can be accomplished in the presence of thionyl chloride.[7]

Pharmacokinetics

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.[8]

See also

References

  1. ↑ Malykh AG; Sadaie MR (Feb 2010). "Piracetam and piracetam-like drugs: from basic science to novel clinical applications to CNS disorders.". Drugs. 70 (3): 287–312. doi:10.2165/11319230-000000000-00000. PMID 20166767.
  2. ↑ Nakamura K; Kurasawa M (May 2001). "Anxiolytic effects of aniracetam in three different mouse models of anxiety and the underlying mechanism". Eur J Pharmacol. (Kanagawa, Japan). 420 (1): 33–43. doi:10.1016/S0014-2999(01)01005-6. PMID 11412837.
  3. ↑ Ito; Tanabe, S; Kohda, A; Sugiyama, H et al. (1990). "Allosteric potentiation of quisqualate receptors by a nootropic drug aniracetam". J. Physiol. 424: 533–543. PMC 1189827. PMID 1975272.
  4. ↑ US 6730677, "Benzofurazan compounds which enhance AMPA receptor activity"
  5. ↑ Patent EP 5 143 Hoffmann-La Roche 1978
  6. ↑ Patent EP 44 088 Hoffmann-La Roche 1978
  7. ↑ 7.0 7.1 A. Kleemann, J. Engel, B. Kutscher, D. Reichert: Pharmaceutical Substances - Synthesis, Patents, Applications, 4. Auflage, Thieme 2001, ISBN 3-13-115134-X.
  8. ↑ Lee, CR; Benfield, P (1994). "Aniracetam. An overview of its pharmacodynamic and pharmacokinetic properties, and a review of its therapeutic potential in senile cognitive disorders". Drugs & aging 4 (3): 257–73. doi:10.2165/00002512-199404030-00007. PMID 8199398.