72432-10-1

Description

Aniracetam, also known as N-anisoyl-2-pyrrolidinone, belongs to the same class of drugs as piracetam and nefiracetam, known for metabolizing in brain cells. As a non-NMDA receptor agent, it is utilized for treating cognitive impairment. Aniracetam enhances synaptic neuron phospholipase activity, increases ATP formation and transport in the brain, boosts protein synthesis and RNA, and promotes the utilization of amino acids, phospholipids, glucose, and oxygen, leading to improved patient response, excitability, and memory.

Chemical Properties

Crystalline Solid

Originator

Roche (Switzerland)

Uses

As a fat-soluble ampakine nootropic, Aniracetam primarily acts as a stimulant and mental enhancer, making users more awake and alert, akin to caffeine. It is known to improve memory, concentration, and neural signaling across synapses. Derived from γ-aminobutyric acid, Aniracetam selectively affects the central nervous system, activating brain cell metabolism, protecting nerve cells, and promoting intelligence through the glutamate receptor system. It has demonstrated efficacy in preventing memory dysfunction caused by various factors and exhibits no sedative or excitatory effects. While available in Europe as a prescription drug, it is not approved by the FDA for use in the United States.

Definition

ChEBI: Aniracetam is a member of pyrrolidin-2-ones and a N-acylpyrrolidine with anti-depressive properties used as a mental performance enhancer.

Preparation

Aniracetam is prepared by condensing 2-pyrrolidone with 4-methoxybenzoyl chloride. The drug was first made in the 1970s by Hoffmann-La Roche. This piracetam-related cognition enhancer reduces glutamate receptor desensitization.

Manufacturing Process

40.0 g of p-methoxybenzoyl chloride, 25.0 g of 2-pyrrolidinone and 110 ml of absolute diethyl ether are treated at between 0°C and 10°C while stirring with 52.5 ml of triethylamine. The mixture is stirred at room temperature for a further 30 minutes and at reflux for 3 hours, then cooled down and treated at 2°C with cold water. The insoluble constituents are filtered off under suction and washed with water and diethyl ether. The thus obtained solid substance is recrystallized from alcohol after drying over phosphorus pentoxide. There is obtained 1-(p-methoxybenzoyl)-2-pyrrolidinone which melts at 121°-122°C.

Brand name

Draganon (Roche, Switzerland), Sarpul (Toyama, Japan), Ampamet(Menarini Group, Italy).

Therapeutic Function

Nootropic

Biological Activity

Nootropic, with modulatory actions through allosteric potentiation of AMPA specific receptors, reduction of glutamate receptor desensitization and potentiation of metabotropic glutamate receptor activity. Anxiolytic following systemic administration.

Pharmacology

Considered more effective than piracetam with minimal side effects, Aniracetam is well-tolerated and efficacious in improving saccade velocity, complex reaction time, and overall performance. It acts as an AMPA receptor potentiator and cognition enhancer related to Piracetam. Used as a nootropic drug, Aniracetam ameliorates memory and attention disturbances associated with cerebrovascular diseases and degenerative brain disorders. It possesses anti-depressive properties, functioning as a mental performance enhancer by slowing ion-channel closing and modulating AMPA receptors involved in glutamate utilization.

Purification Methods

Purify aniracetam by recrystallisation from EtOH. It is a nootropic (Alzheimer) drug. [Gouliaev & Senning Brain Research Rev 19 180 1994.]