72432-10-1 Usage
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
Crystalline Solid
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 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 lookchem of Dai Xiongfeng.
Purification Methods
Purify aniracetam by recrystallisation from EtOH. It is a nootropic (Alzheimer) drug. [Gouliaev & Senning Brain Research Rev 19 180 1994.]
references
[1] mizuki y, yamada m, kato i, et al. effects of aniracetam, a nootropic drug, in senile dementia. a preliminary report.: a preliminary report. the kurume medical journal, 1984, 31(2): 135-143.[2] cumin r, bandle e f, gamzu e, et al. effects of the novel compound aniracetam (ro 13-5057) upon impaired learning and memory in rodents. psychopharmacology, 1982, 78(2): 104-111.
Check Digit Verification of cas no
The CAS Registry Mumber 72432-10-1 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 7,2,4,3 and 2 respectively; the second part has 2 digits, 1 and 0 respectively.
Calculate Digit Verification of CAS Registry Number 72432-10:
(7*7)+(6*2)+(5*4)+(4*3)+(3*2)+(2*1)+(1*0)=101
101 % 10 = 1
So 72432-10-1 is a valid CAS Registry Number.
InChI:InChI=1/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
72432-10-1Relevant articles and documents
A Unified Strategy for the Synthesis of Difluoromethyl- And Vinylfluoride-Containing Scaffolds
Duchemin, Nicolas,Buccafusca, Roberto,Daumas, Marc,Ferey, Vincent,Arseniyadis, Stellios
supporting information, p. 8205 - 8210 (2019/10/16)
Here, we report a general method for the synthesis of quaternary and tertiary difluoromethylated compounds and their vinylfluoride analogues. The strategy, which relies on a two-step sequence featuring a C-selective electrophilic difluoromethylation and either a palladium-catalyzed decarboxylative protonation or a Krapcho decarboxylation, is practical, scalable, and high yielding. Considering the generality of the method and the attractive properties offered by the difluoromethyl group, this approach provides a valuable tool for late-stage functionalization and drug development.
Preparation method of aniracetam
-
Paragraph 0018; 0042-0055, (2019/04/04)
The invention belongs to the field of medicinal chemistry, and in particular relates to a preparation method of aniracetam. According to the preparation method of the aniracetam provided by the invention, a mixed acid anhydride intermediate is firstly generated by p-methoxybenzoic acid and pivaloyl chloride, and then the mixed acid anhydride intermediate reacts with 2-pyrrolidone to form a targetproduct, namely aniracetam. Therefore, the preparation method of the aniracetam has the advantages that the reaction steps are short, the reaction yield and the product purity are relatively high, rawmaterials are low in cost and easy to obtain, the operation is simple, and the method is suitable for large-scale industrial production and the like.
CuCl/TMEDA/nor-AZADO-catalyzed aerobic oxidative acylation of amides with alcohols to produce imides
Kataoka, Kengo,Wachi, Keiju,Jin, Xiongjie,Suzuki, Kosuke,Sasano, Yusuke,Iwabuchi, Yoshiharu,Hasegawa, Jun-Ya,Mizuno, Noritaka,Yamaguchi, Kazuya
, p. 4756 - 4768 (2018/06/07)
Although aerobic oxidative acylation of amides with alcohols would be a good complement to classical synthetic methods for imides (e.g., acylation of amides with activated forms of carboxylic acids), to date, there have been no reports on oxidative acylation to produce imides. In this study, we successfully developed, for the first time, an efficient method for the synthesis of imides through aerobic oxidative acylation of amides with alcohols by employing a CuCl/TMEDA/nor-AZADO catalyst system (TMEDA = teramethylethylendiamine; nor-AZADO = 9-azanoradamantane N-oxyl). The proposed acylation proceeds through the following sequential reactions: aerobic oxidation of alcohols to aldehydes, nucleophilic addition of amides to the aldehydes to form hemiamidal intermediates, and aerobic oxidation of the hemiamidal intermediates to give the corresponding imides. This catalytic system utilizes O2 as the terminal oxidant and produces water as the sole by-product. An important point for realizing this efficient acylation system is the utilization of a TMEDA ligand, which, to the best of our knowledge, has not been employed in previously reported Cu/ligand/N-oxyl systems. Based on experimental evidence, we consider that plausible roles of TMEDA involve the promotion of both hemiamidal oxidation and regeneration of an active CuII-OH species from a CuI species. Here promotion of hemiamidal oxidation is particularly important. Employing the proposed system, various types of structurally diverse imides could be synthesized from various combinations of alcohols and amides, and gram-scale acylation was also successful. In addition, the proposed system was further applicable to the synthesis of α-ketocarbonyl compounds (i.e., α-ketoimides, α-ketoamides, and α-ketoesters) from 1,2-diols and nucleophiles (i.e., amides, amines, and alcohols).
