Aniracetam

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Aniracetam
Systematic (IUPAC) name
1-[(4-methoxybenzoyl)]- 2-pyrrolidinone
Clinical data
Trade namesAmpamet, Memodrin, Pergamid
AHFS/Drugs.comInternational Drug Names
Pregnancy cat. ?
Legal statusUnscheduled
RoutesOral
Pharmacokinetic data
Half-life1-2.5 hours
Identifiers
CAS number72432-10-1 N
ATC codeN06BX11
PubChemCID 2196
DrugBankDB04599
ChemSpider2111 YesY
UNII5L16LKN964 YesY
KEGGD01883 YesY
ChEBICHEBI:47943 YesY
ChEMBLCHEMBL36994 YesY
Chemical data
FormulaC12H13NO3 
Mol. mass219.237 g/mol
 N (what is this?)  (verify)
 
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Aniracetam
Systematic (IUPAC) name
1-[(4-methoxybenzoyl)]- 2-pyrrolidinone
Clinical data
Trade namesAmpamet, Memodrin, Pergamid
AHFS/Drugs.comInternational Drug Names
Pregnancy cat. ?
Legal statusUnscheduled
RoutesOral
Pharmacokinetic data
Half-life1-2.5 hours
Identifiers
CAS number72432-10-1 N
ATC codeN06BX11
PubChemCID 2196
DrugBankDB04599
ChemSpider2111 YesY
UNII5L16LKN964 YesY
KEGGD01883 YesY
ChEBICHEBI:47943 YesY
ChEMBLCHEMBL36994 YesY
Chemical data
FormulaC12H13NO3 
Mol. mass219.237 g/mol
 N (what is this?)  (verify)

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, but can be purchased in most countries without a prescription.

Contents

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 facilitated by D2/D3, nACh, and 5-HT2A receptors.[1]

Aniracetam has also been shown to selectively modulate the AMPA receptor[2] 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.1

Despite the fat solubility of aniracetam, its half-life is much shorter than that of common racetam analogs such as piracetam.[citation needed]

Commonly used doses are 750-3,000 mg daily usually taken in 2-3 doses.

Side Effects

Common side effects consist of: unrest, anxiety, uneasiness, insomnia. Less common adverse effects include: headaches, somnolence, vertigo, mild epigastric pain, nausea, diarrhea, rash. These effects are generally temporary, and in the studies where they were reported as adverse events, did not require termination of treatment.[3]

Synthesis

The drug was first made in the 1970s by Hoffmann-La Roche.[4][5] Synthesis can be caused by 2-Pyrrolidone reacting with Anisoyl chloride in the presence of Triethylamine.[6]

Aniracetam synthesis 01.svg

Alternatively, gamma-Aminobutyric acid can react with anisoyl chloride. Ring closure can be accomplished with the presence of Thionyl chloride.[6]

Aniracetam synthesis 02.svg

Pharmacokinetics

The primary metabolites of aniracetam are N-anisoyl-GABA, 2-Pyrrolidone, and Anisic acid.[7]

See also

References

  1. ^ 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.
  2. ^ Ito et al. J. Physiol. 1990; 424: 533-543.
  3. ^ "Aniracetam: Smarter Nootropics". March 20, 2012. http://www.smarternootropics.com/table-of-contents/aniracetam/. Retrieved April 11, 2012.
  4. ^ Patent EP 5 143 Hoffmann-La Roche 1978.
  5. ^ Patent EP 44 088 Hoffmann-La Roche 1978.
  6. ^ a b A. Kleemann, J. Engel, B. Kutscher, D. Reichert: Pharmaceutical Substances - Synthesis, Patents, Applications, 4. Auflage, Thieme 2001, ISBN 3-13-115134-X.
  7. ^ abstract at PMID 8199398

External links