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| CAS No.: | 72432-10-1 |
|---|---|
| Name: | Aniracetam |
| Article Data: | 13 |
| Molecular Structure: | |
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| Formula: | C12H13NO3 |
| Molecular Weight: | 219.24 |
| Synonyms: | Ampamet;Draganon;Ro 13-3057;Ro 13-5057/001;Sarpul; |
| EINECS: | 615-758-3 |
| Density: | 1.236 g/cm3 |
| Melting Point: | ?58°C(lit.) |
| Boiling Point: | 399.7 °C at 760 mmHg |
| Flash Point: | 195.5 °C |
| Solubility: | Soluble in chloroform. Also soluble in ethanol. Insoluble in water |
| Appearance: | White Crystalline or Crystalline Powde |
| PSA: | 46.61000 |
| LogP: | 1.39570 |
| Conditions | Yield |
|---|---|
| With silica gel In toluene Concentration; Reagent/catalyst; Reflux; | 91% |
| With phenylboronic acid In benzene for 16h; Reagent/catalyst; Reflux; Green chemistry; | 84.6% |
| With zirconyl chloride octahydrate In chlorobenzene at 131℃; for 18h; Dean-Stark; | 79% |
| Stage #1: 4-methoxybenzoic acid With thionyl chloride at 76℃; for 3h; Stage #2: 2-pyrrolidinon With triethylamine In toluene at 50 - 110℃; for 2.5h; |
| Conditions | Yield |
|---|---|
| With bis[2-(diphenylphosphino)phenyl] ether; palladium(II) iodide In toluene at 105℃; under 37503.8 Torr; for 20h; Inert atmosphere; Autoclave; regioselective reaction; | 89% |
| Conditions | Yield |
|---|---|
| With triethylamine In tetrahydrofuran at 0 - 20℃; | 83% |
| With triethylamine In dichloromethane at 0℃; for 1h; Inert atmosphere; | 80% |
| With triethylamine In diethyl ether; water |
1-(4-methoxybenzoyl)pyrrolidine
aniracetam
| Conditions | Yield |
|---|---|
| With CrO3-3.5-dimethylpyrazole In dichloromethane for 24h; Ambient temperature; | 70% |
| Conditions | Yield |
|---|---|
| With Shvo's Catalyst In toluene at 100℃; for 24h; Inert atmosphere; | 40% |
| Conditions | Yield |
|---|---|
| With thionyl chloride In dichloromethane; toluene |
| Conditions | Yield |
|---|---|
| In N-methyl-acetamide; phosphorus pentaoxide; diethyl ether |
4-acetoxy-2-pyrrolidinone
1-(4-methoxybenzoyl)-1,5-dihydro-2H-pyrrol-2-one
4-methoxy-benzoyl chloride
aniracetam
| Conditions | Yield |
|---|---|
| With chloro-trimethyl-silane; sodium hydrogencarbonate; triethylamine; carbon palladium In tetrahydrofuran; ethyl acetate |
| Conditions | Yield |
|---|---|
| With hydrogenchloride; sodium hydroxide; phosphoric acid In phosphorus pentaoxide; water; acetone; Petroleum ether; 4-amino-n-butyric acid |
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The Aniracetam is an ampakine and nootropic of the racetam chemical class with the formula C12H13NO3. The IUPAC name of this chemical is 1-(4-methoxybenzoyl)pyrrolidin-2-one. With the CAS registry number 72432-10-1, it is also named as 1-(4-Methoxybenzoyl)-2-pyrrolidinone; Draganon. The product's categorie is Glutamate.
The other characteristics of this product can be summarized as: (1)ACD/LogP: 0.27; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 0.27; (4)ACD/LogD (pH 7.4): 0.27; (5)ACD/BCF (pH 5.5): 1; (6)ACD/BCF (pH 7.4): 1; (7)ACD/KOC (pH 5.5): 33.46; (8)ACD/KOC (pH 7.4): 33.46; (9)#H bond acceptors: 4; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 2; (12)Index of Refraction: 1.573; (13)Molar Refractivity: 58.46 cm3; (14)Molar Volume: 177.2 cm3; (15)Polarizability: 23.17 10-24cm3; (16)Surface Tension: 49.2 dyne/cm; (17)Enthalpy of Vaporization: 65.05 kJ/mol; (18)Vapour Pressure: 1.34E-06 mmHg at 25°C; (19)Rotatable Bond Count: 2; (20)Tautomer Count: 2; (21)Exact Mass: 219.089543; (22)MonoIsotopic Mass: 219.089543; (23)Topological Polar Surface Area: 46.6; (24)Heavy Atom Count: 16.
Preparation of Aniracetam: It can be obtained by pyrrolidin-2-one and 4-methoxy-benzoyl chloride with the reagent Et3N in the solvent tetrahydrofuran at the temperature of 0-20 °C. The yield is 83 %.
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Uses of Aniracetam: It has also been shown to selectively modulate the AMPA glutamate receptor and was used as the parent compound to derive a class of drugs known as the ampakines which are being investigated as nootropics and neuroprotective drugs for the treatment of Alzheimer's disease and other neurodegenerative conditions. Despite the fat solubility of aniracetam its half-life is much shorter than common racetam analogs such as Piracetam. Side effects can include nausea and headache.
People can use the following data to convert to the molecule structure.
1. SMILES: O=C2N(C(=O)c1ccc(OC)cc1)CCC2;
2. 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.
The following are the toxicity data which has been tested.
| Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
|---|---|---|---|---|---|
| mouse | LD50 | intraperitoneal | 1180mg/kg (1180mg/kg) | SENSE ORGANS AND SPECIAL SENSES: LACRIMATION: EYE BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD | Yakuri to Chiryo. Pharmacology and Therapeutics. Vol. 14(Suppl, |
| mouse | LD50 | intravenous | > 100mg/kg (100mg/kg) | Medicamentos de Actualidad. Vol. 30, Pg. 9, 1994. | |
| mouse | LD50 | oral | 3648mg/kg (3648mg/kg) | BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD GASTROINTESTINAL: CHANGES IN STRUCTURE OR FUNCTION OF SALIVARY GLANDS | Yakuri to Chiryo. Pharmacology and Therapeutics. Vol. 14(Suppl, |
| mouse | LD50 | subcutaneous | > 5gm/kg (5000mg/kg) | Drugs in Japan Vol. -, Pg. 45, 1995. | |
| rabbit | LD50 | oral | > 2gm/kg (2000mg/kg) | Medicamentos de Actualidad. Vol. 30, Pg. 9, 1994. | |
| rat | LD50 | intraperitoneal | 1255mg/kg (1255mg/kg) | Medicamentos de Actualidad. Vol. 30, Pg. 9, 1994. | |
| rat | LD50 | intravenous | > 50mg/kg (50mg/kg) | Medicamentos de Actualidad. Vol. 30, Pg. 9, 1994. | |
| rat | LD50 | oral | 4500mg/kg (4500mg/kg) | Psychopharmacology Vol. 78, Pg. 104, 1982. | |
| rat | LD50 | subcutaneous | > 5gm/kg (5000mg/kg) | Drugs in Japan Vol. -, Pg. 45, 1995. |
