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
Method for catalytically oxidizing amine to be synthesized into amide through dipyridyl-type manganese catalyst
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Paragraph 0017-0027; 0052-0054, (2019/06/30)
The invention discloses a methodfor catalytically oxidizing amine to be synthesized into amide througha dipyridyl-type manganese catalyst. According to the method, a dipyridyl manganese complex formedafter coordination of a dipyridyl-type complex and cheap metal manganese serves as the catalyst, clean and environment-friendly hydrogen peroxide serves as an oxidizing agent, oxidation of N ortho-position sp3 C-H bonds catalyzed by the cheap metal manganese is achieved, and the amine is directly oxidized to obtain the amide. Compared with existing methods, the method has the advantages that theadopted catalyst is low in price, the preparing method is simple, raw materials are easy to obtain, the use level of the catalyst is low, the substrate range is wide, the reaction condition is mild, the operation is simple and environmentally friendly, the reaction time is short, the yield is high, the selectivity is high, and the industrialization cost is low.
Catalytic synthesis method of Aniracetam
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Paragraph 0058; 0059; 0061; 0062; 0063-0073, (2019/05/08)
The invention belongs to the technical field of drug synthesis, and in particular relates to a catalytic synthesis method of Aniracetam. The catalytic synthesis method comprises the steps as follows:adding an organic solvent, p-methoxybenzoic acid, 2-pyrrolidone and a boric acid catalyst into a reaction vessel, reacting completely, and performing post-treatment to obtain Aniracetam. The catalyticeffect of the boric acid catalyst is remarkable, and the catalyst itself is cheap and easily available, thereby producing high economic efficiency. The catalytic synthesis method has high atomic utilization rate, and the by-product produced by the method is water, which causes no pollution to the environment. The catalytic synthesis method is easy to operate, and the reaction yield and product purity are high. In summary, the catalytic synthesis method of Aniracetam adopts a green environmentally-friendly preparation process, which is low-cost and especially suitable for large-scale industrial production. Thereby, the method of the invention has a broad application prospect and good market potential.
Preparation method of aniracetam
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Paragraph 0036-0049, (2018/05/24)
The invention relates to the field of medicinal chemistry and particularly relates to a preparation method of aniracetam. The synthesis route of aniracetam is shown in the description.
