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Aniracetam

CAS No.72432-10-1
Chemical Name:Aniracetam
CBNumber:CB6185499
Molecular Formula:C12H13NO3
Formula Weight:219.24
MOL File:72432-10-1.mol

Aniracetam Property

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)
pka -1.74±0.20(Predicted)
form Solid
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)
FDA UNII 5L16LKN964
ATC code N06BX11
UNSPSC Code 12352200
NACRES NA.77

Safety

WGK Germany :2
RTECS :UY5781900
HS Code :2933.79.1500
Toxicity :LD50 in rats, mice (mg/kg): ~4500, >5000 orally (Cumin)

Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal wordWarning
Hazard statements H303
Precautionary statements P270-P301+P312-P403-P501c

Aniracetam Price More Price(3)

Brand: Sigma-Aldrich(India)
Product number: 5.04913
Product name : Aniracetam - CAS 72432-10-1 - Calbiochem
Purity:
Packaging: 50MG
Price: ₹12940
Updated: 2022/06/14
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Brand: TCI Chemicals (India)
Product number: A2394
Product name : Aniracetam
Purity: min. 98.0 %
Packaging: 1G
Price: ₹5600
Updated: 2022/05/26
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Brand: TCI Chemicals (India)
Product number: A2394
Product name : Aniracetam
Purity: min. 98.0 %
Packaging: 5G
Price: ₹10800
Updated: 2022/05/26
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Aniracetam Chemical Properties,Usage,Production

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