Aniracetam
[CAS# 72432-10-1]

Identification

• Classification: API >> Nervous system medication >> Brain metabolism regulating drug
• Name: Aniracetam
• Synonyms: 1-(4-Methoxybenzoyl)-2-pyrrolidinone
• Molecular Formula: C₁₂H₁₃NO₃
• Molecular Weight: 219.24
• CAS Registry Number: 72432-10-1
• EC Number: 615-758-3
• SMILES: COC1=CC=C(C=C1)C(=O)N2CCCC2=O

Properties

• Density: 1.2±0.1 g/cm³ Calc.^*
• Boiling point: 399.7±34.0 °C 760 mmHg (Calc.)^*
• Flash point: 195.5±25.7 °C (Calc.)^*
• Solubility: DMSO 44 mg/mL, water: 100 mM (Expl.)
• Index of refraction: 1.574 (Calc.)^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Safety Data

• Hazard Symbols: GHS08 Warning
• Risk Statements: H361
• Safety Statements: P203-P280-P318-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Reproductive toxicity	Repr.	2	H361

Discovery and Applications

Aniracetam is a synthetic nootropic compound belonging to the racetam family, characterized structurally by a pyrrolidone nucleus substituted with a methoxybenzoyl group. Its IUPAC name is 1-(4-methoxybenzoyl)-2-pyrrolidinone. The compound was first developed in the 1970s by Hoffmann-La Roche and has since been studied primarily for its potential cognitive-enhancing properties and effects on memory and learning.

The synthesis of aniracetam typically involves the acylation of 2-pyrrolidone with 4-methoxybenzoyl chloride under basic or acidic conditions, leading to the formation of the amide linkage between the pyrrolidone nitrogen and the benzoyl carbon. This process yields a compound that maintains the core structure common to racetams, which are known for their activity on the central nervous system.

Chemically, aniracetam is a white to off-white crystalline powder, slightly soluble in water and more soluble in lipophilic solvents such as ethanol or dimethyl sulfoxide. The methoxy group at the para position of the aromatic ring influences the compound’s polarity and may affect its pharmacokinetic profile. Aniracetam is relatively stable under standard storage conditions, although it should be protected from excessive heat and moisture.

Aniracetam is primarily used and studied in the context of neuroscience and pharmacology. It has been reported to modulate AMPA receptors, a subtype of ionotropic glutamate receptors in the brain, though the exact mechanism of action remains incompletely defined. Its activity is often described as enhancing cholinergic transmission, and it has been explored for its potential to improve cognitive functions, such as learning and memory, in preclinical and some human studies. However, its use is not approved as a prescription medication in most countries and is generally categorized as a dietary supplement or investigational compound.

Applications of aniracetam are mainly found in experimental pharmacology and neurobiology. It has been studied in models of age-related cognitive decline and neurological disorders to evaluate its neuroprotective potential. Some research has also examined its influence on mood and anxiety-like behaviors, though clinical evidence remains limited and inconclusive. Unlike many traditional drugs, aniracetam is not widely regulated, and its use varies by jurisdiction.

Analytical methods for identifying and quantifying aniracetam include high-performance liquid chromatography (HPLC), nuclear magnetic resonance (¹H and ¹³C NMR) spectroscopy, and mass spectrometry. These techniques confirm the structure, purity, and stability of the compound, as well as help detect potential impurities during synthesis and formulation.

In terms of safety and pharmacology, aniracetam is generally reported to have a favorable safety profile in animal models at therapeutic doses. It is known to undergo rapid metabolism in the liver, with its primary metabolites including N-anisoyl-GABA and 2-pyrrolidone. These metabolites may also contribute to its biological activity.

In summary, aniracetam is a well-defined member of the racetam family developed for potential cognitive enhancement. Its chemical structure, synthesis, and functional profile have been extensively studied, especially in the context of neuroscience research. While it is not an approved therapeutic agent in most countries, it continues to be of interest in experimental pharmacology for its effects on neurotransmission and cognitive function.

References

2023. The Origins and Background of the Creation of the Nootropics Concept. Neurochemical Journal, 17(2).
DOI: 10.1134/s1819712423020125

1984. Effects of aniracetam, a nootropic drug, in senile dementia. A preliminary report. The Kurume Medical Journal, 31(2).
DOI: 10.2739/kurumemedj.31.135

1982. Effects of the novel compound aniracetam (Ro 13-5057) upon impaired learning and memory in rodents. Psychopharmacology, 78(2).
DOI: 10.1007/bf00432244