Aniracetam Chemical Properties

Melting point:

121-122?C

Boiling point:

399.7±34.0 °C(Predicted)

Density 

1.236±0.06 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

solubility 

Chloroform (Slightly), Methanol (Slightly)

form 

Solid

pka

-1.74±0.20(Predicted)

color 

White

Water Solubility 

Soluble in chloroform. Also soluble in ethanol. Insoluble in water

Merck 

14,662

InChI

InChI=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

InChIKey

ZXNRTKGTQJPIJK-UHFFFAOYSA-N

SMILES

N1(C(=O)C2=CC=C(OC)C=C2)CCCC1=O

CAS DataBase Reference

72432-10-1(CAS DataBase Reference)

Safety Information

WGK Germany 

2

RTECS 

UY5781900

HS Code 

2933.79.1500

Toxicity

LD50 in rats, mice (mg/kg): ~4500, >5000 orally (Cumin)

MSDS

• Language:English Provider:1-(4-Methoxybenzoyl)-2-pyrrolidinone
• Language:English Provider:SigmaAldrich

Aniracetam Usage And Synthesis

Description

Aniracetam, also known as N-anisoyl-2-pyrrolidinone, together with piracetam and nefiracetam, belong to the same class of piracetam metabolized drugs of brain cells. It is a non-NMDA receptor agent useful for the treatment of cognitive impairment. These drugs can enhance the activity of synaptic neurons phospholipase, increase the ATP formation and transport in brain, increase protein synthesis and RNA, promote the usage of brain on amino acids, phospholipids, glucose and oxygen, increase the patient's response, excitability and memory. Aniracetam has a higher effect than piracetam, but with a relatively minor side effect. It is well tolerated and efficacious in improving velocity and accuracy of the saccades, complex reaction time, and other aspects of performance.

Chemical Properties

Aniracetam is a white or colorless solid. It has a molecular structure that consists of an organic compound with a methoxy group attached to one side of a benzene ring, and a carboxylic acid group attached to the other side. It forms crystals when dissolved in ethanol, and has a melting point of 121-122°C. Exhibits acute toxicity in rats and mice, with LD50 values of approximately 4500mg/kg and >5000mg/kg when administered orally.

Originator

Roche (Switzerland)

Uses

Aniracetam is AMPA receptor potentiator with Cognition enhancer related to Piracetam. It is used as a nootropic drug to ameliorate memory and attention disturbances accompanying cerebrovascular diseases and degenerative brain disorders. Compound with anti-depressive properties used as a mental performance enhancer. Slows the rate of ion-channel closing.

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

benefits

Aniracetam[72432-10-1] is in the racetam-family of nootropic compounds. It is a fat-soluble ampakine nootropic. Aniracetam primarily acts as both a stimulant and a mental enhancer. It’s said to help make you more awake and alert. This is similar to caffeine. It may also help improve your memory and concentration.
Aniracetam modulates AMPA receptors which are involved in how glutamate is used in your brain. More of the neurotransmitter glutamate is available. Which means better neural signaling across synapses. Your brain is working optimally despite stress, fatigue and anxiety.

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

Aniracetam, a cyclized derivative of γ-aminobutyric acid, can improve the brain function. It can selectively exert effect on central nervous system through penetration into blood-brain barrier. It can activate the metabolism activity of brain cell and protect the nerve cells. This product can also promote the intelligence by affecting the glutamate receptor system. Moreover, it improves skin’s resistance to hypoxia, preventing the occurrence of malfunction of learning and memory caused by a variety of chemical substances, hypercapnia, scopolamine and electrical shock. This product has no sedative or excitation effect. Animal experiments show that this product promotes the memory recovery in normal rats' learning process. It can fight against hypoxia-induced memory recession and relieve the memory malfunction caused by certain reasons.
The above information is edited by the Chemicalbook of Dai Xiongfeng.

storage

Room temperature

Purification Methods

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

References

[1] C R LEE P B. Aniracetam. An overview of its pharmacodynamic and pharmacokinetic properties, and a review of its therapeutic potential in senile cognitive disorders.[J]. Drugs & Aging, 1994, 4 3: 257-273. DOI:10.2165/00002512-199404030-00007.
[2] U SENIN. Aniracetam (Ro 13-5057) in the treatment of senile dementia of Alzheimer type (SDAT): results of a placebo controlled multicentre clinical study.[J]. European Neuropsychopharmacology, 1991, 1 4: 511-517. DOI:10.1016/0924-977x(91)90004-e.
[3] Y MIZUKI. Effects of aniracetam, a nootropic drug, in senile dementia–a preliminary report.[J]. Kurume Medical Journal, 1984, 31 2: 135-143. DOI:10.2739/kurumemedj.31.135.
[4] R CUMIN. Effects of the novel compound aniracetam (Ro 13-5057) upon impaired learning and memory in rodents.[J]. Psychopharmacology, 1982, 78 2: 104-111. DOI:10.1007/BF00432244.

Aniracetam(72432-10-1)Related Product Information

• Gabapentin
• Pramiracetam
• Oxiracetam
• Nefiracetam
• Piracetam
• N-Vinyl-2-pyrrolidone
• Aniracetam
• 2-Pyrrolidinone
• Polyvinylpyrrolidone
• Povidone iodine
• N-Methyl-2-pyrrolidone
• METHYL-2-PYRROLIDONE
• Benzene
• (S)-3-Hydroxy-1-(3-hydroxy-4-methoxybenzoyl)-2-pyrrolidinone
• Ethyl 1-(4-methoxybenzoyl)-2-oxo-4-phenyl-3-pyrrolidinecarboxylate
• 1-(3-Hydroxy-4-methoxybenzoyl)-2-pyrrolidinone
• 4-(4-Chlorophenyl)-1-(4-methoxybenzoyl)-2-pyrrolidinone
• TOSLAB 12738