| Identification | More | [Name]
Aniracetam | [CAS]
72432-10-1 | [Synonyms]
1-(4-METHOXYBENZOYL)-2-PYRROLIDINONE
ANIRACETAM
RO 13-5057
1-(4-methoxybenzoyl)-2-pyrrolidinon
1-(p-methoxybenzoyl)-2-pyrrolidinon
1-p-anisoyl-2-pyrrolidinone
draganon
sarpul
2-PYRROLIDINONE,1-(4-METHOXYBENZOYL)
1-(4-Methoxybenzoyl)-2-pyrrolidinone, Ro 13-5057
1-(4-Methoxybenzoyl)pyrrolidin-2-one
Ro-13-5057/001 | [EINECS(EC#)]
615-758-3 | [Molecular Formula]
C12H13NO3 | [MDL Number]
MFCD00153767 | [Molecular Weight]
219.24 | [MOL File]
72432-10-1.mol |
| Chemical Properties | Back Directory | [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 Data | Back Directory | [WGK Germany ]
2
| [RTECS ]
UY5781900
| [HS Code ]
2933.79.1500 | [Toxicity]
LD50 in rats, mice (mg/kg): ~4500, >5000 orally (Cumin) |
| Hazard Information | Back Directory | [Description]
Aniracetam(cas 72432-10-1) is a non-NMDA receptor agent useful for the treatment of cognitive impairment. In a clinical study, it showed good to very good improvement in 60% of patients with cerebral insufficiency. Statistically significant improvement in the psychobehavioral parameters has been observed in a group of patients with senile dementia of the Alzheimer’s type. Aniracetam is well tolerated and efficacious in improving velocity and accuracy of the saccades, complex reaction time, and other aspects of performance compared with placebo group in hypoxic volunteers. Its nootropic property has been attributed to the cholinergic blockade. | [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; Sarpul;Ampamet; Reset | [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] 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. |
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