Product Name

  • Name

    Aniracetam

  • EINECS 615-758-3
  • CAS No. 72432-10-1
  • Article Data13
  • CAS DataBase
  • Density 1.236 g/cm3
  • Solubility Soluble in chloroform. Also soluble in ethanol. Insoluble in water
  • Melting Point ?58°C(lit.)
  • Formula C12H13NO3
  • Boiling Point 399.7 °C at 760 mmHg
  • Molecular Weight 219.24
  • Flash Point 195.5 °C
  • Transport Information
  • Appearance White Crystalline or Crystalline Powde
  • Safety
  • Risk Codes
  • Molecular Structure Molecular Structure of 72432-10-1 (Aniracetam)
  • Hazard Symbols
  • Synonyms Ampamet;Draganon;Ro 13-3057;Ro 13-5057/001;Sarpul;
  • PSA 46.61000
  • LogP 1.39570

Synthetic route

4-Methoxybenzyl alcohol

4-Methoxybenzyl alcohol

aniracetam
72432-10-1

aniracetam

2-pyrrolidinon
616-45-5

2-pyrrolidinon

4-methoxybenzoic acid
100-09-4

4-methoxybenzoic acid

aniracetam
72432-10-1

aniracetam

Conditions
ConditionsYield
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;
carbon monoxide
201230-82-2

carbon monoxide

4-methoxy-N-prop-2-enylbenzamide
66897-25-4

4-methoxy-N-prop-2-enylbenzamide

aniracetam
72432-10-1

aniracetam

Conditions
ConditionsYield
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%
2-pyrrolidinon
616-45-5

2-pyrrolidinon

4-methoxy-benzoyl chloride
100-07-2

4-methoxy-benzoyl chloride

aniracetam
72432-10-1

aniracetam

Conditions
ConditionsYield
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
69838-98-8

1-(4-methoxybenzoyl)pyrrolidine

aniracetam
72432-10-1

aniracetam

Conditions
ConditionsYield
With CrO3-3.5-dimethylpyrazole In dichloromethane for 24h; Ambient temperature;70%
2-pyrrolidinon
616-45-5

2-pyrrolidinon

4-methoxy-benzaldehyde
123-11-5

4-methoxy-benzaldehyde

aniracetam
72432-10-1

aniracetam

Conditions
ConditionsYield
With Shvo's Catalyst In toluene at 100℃; for 24h; Inert atmosphere;40%
pyrographite
7440-44-0

pyrographite

Anisamidobutyric acid
72432-14-5

Anisamidobutyric acid

aniracetam
72432-10-1

aniracetam

Conditions
ConditionsYield
With thionyl chloride In dichloromethane; toluene
sodium salt of 2-pyrrolidinone
3195-95-7

sodium salt of 2-pyrrolidinone

4-methoxy-benzoyl chloride
100-07-2

4-methoxy-benzoyl chloride

aniracetam
72432-10-1

aniracetam

Conditions
ConditionsYield
In N-methyl-acetamide; phosphorus pentaoxide; diethyl ether
4-acetoxy-2-pyrrolidinone
64097-45-6

4-acetoxy-2-pyrrolidinone

1-(4-methoxybenzoyl)-1,5-dihydro-2H-pyrrol-2-one
72432-11-2

1-(4-methoxybenzoyl)-1,5-dihydro-2H-pyrrol-2-one

5-oxo-1-trimethylsilyl-3-pyrrolidinyl acetate

5-oxo-1-trimethylsilyl-3-pyrrolidinyl acetate

4-methoxy-benzoyl chloride
100-07-2

4-methoxy-benzoyl chloride

aniracetam
72432-10-1

aniracetam

Conditions
ConditionsYield
With chloro-trimethyl-silane; sodium hydrogencarbonate; triethylamine; carbon palladium In tetrahydrofuran; ethyl acetate
...Expand
4-methoxy-benzoyl chloride
100-07-2

4-methoxy-benzoyl chloride

Anisamidobutyric acid
72432-14-5

Anisamidobutyric acid

aniracetam
72432-10-1

aniracetam

Conditions
ConditionsYield
With hydrogenchloride; sodium hydroxide; phosphoric acid In phosphorus pentaoxide; water; acetone; Petroleum ether; 4-amino-n-butyric acid
N-trimethylsilyl-pyrrolidin-2-one
14468-90-7

N-trimethylsilyl-pyrrolidin-2-one

4-methoxy-benzoyl chloride
100-07-2

4-methoxy-benzoyl chloride

aniracetam
72432-10-1

aniracetam

Conditions
ConditionsYield
In diethyl ether
2-pyrrolidinon
616-45-5

2-pyrrolidinon

C13H16O4
78823-41-3

C13H16O4

aniracetam
72432-10-1

aniracetam

Conditions
ConditionsYield
In dichloromethane Solvent; Reflux;31.8 g
aniracetam
72432-10-1

aniracetam

Allyl chloroformate
2937-50-0

Allyl chloroformate

allyl 1-(4-methoxybenzoyl)-2-oxopyrrolidine-3-carboxylate

allyl 1-(4-methoxybenzoyl)-2-oxopyrrolidine-3-carboxylate

Conditions
ConditionsYield
Stage #1: aniracetam With lithium hexamethyldisilazane In tetrahydrofuran at -78℃; for 0.25h; Inert atmosphere;
Stage #2: Allyl chloroformate In tetrahydrofuran at -78℃; Inert atmosphere;		99%
aniracetam
72432-10-1

aniracetam

trifluoroacetic anhydride
407-25-0

trifluoroacetic anhydride

A

(Z)-3-(1-chloro-2,2,2-trifluoroethylidene)-1-(4-methoxybenzoyl)pyrrolidin-2-one

(Z)-3-(1-chloro-2,2,2-trifluoroethylidene)-1-(4-methoxybenzoyl)pyrrolidin-2-one

B

(E)-3-(1-chloro-2,2,2-trifluoroethylidene)-1-(4-methoxybenzoyl)pyrrolidin-2-one

(E)-3-(1-chloro-2,2,2-trifluoroethylidene)-1-(4-methoxybenzoyl)pyrrolidin-2-one

Conditions
ConditionsYield
With aluminum (III) chloride In N,N-dimethyl-formamide at 60℃; for 24h; Inert atmosphere; Overall yield = 51 %; Overall yield = 169 mg; stereoselective reaction;A n/a
B n/a
...Expand
aniracetam
72432-10-1

aniracetam

N-[4-(2'-tosyloxyethyloxy)benzoyl]pyrrolidin-2-one

N-[4-(2'-tosyloxyethyloxy)benzoyl]pyrrolidin-2-one

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: trimethylsilyl iodide / chloroform / 18 h / 50 °C
2: caesium carbonate / N,N-dimethyl-formamide / 16 h / 70 °C / Inert atmosphere
View Scheme
aniracetam
72432-10-1

aniracetam

N-[4-(3’-tosyloxypropyloxy)benzoyl]pyrrolidin-2-one

N-[4-(3’-tosyloxypropyloxy)benzoyl]pyrrolidin-2-one

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: trimethylsilyl iodide / chloroform / 18 h / 50 °C
2: caesium carbonate / N,N-dimethyl-formamide / 16 h / 70 °C / Inert atmosphere
View Scheme
aniracetam
72432-10-1

aniracetam

N-[4-(4’-tosyloxybutyloxy)benzoyl]pyrrolidin-2-one

N-[4-(4’-tosyloxybutyloxy)benzoyl]pyrrolidin-2-one

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: trimethylsilyl iodide / chloroform / 18 h / 50 °C
2: caesium carbonate / N,N-dimethyl-formamide / 16 h / 70 °C / Inert atmosphere
View Scheme
aniracetam
72432-10-1

aniracetam

N-[4-(2-fluoroethyloxy)benzoyl]pyrrolidin-2-one

N-[4-(2-fluoroethyloxy)benzoyl]pyrrolidin-2-one

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: trimethylsilyl iodide / chloroform / 18 h / 50 °C
2: caesium carbonate / N,N-dimethyl-formamide / 16 h / 70 °C / Inert atmosphere
View Scheme
aniracetam
72432-10-1

aniracetam

N-[4-(3-fluoropropyloxy)benzoyl]pyrrolidin-2-one

N-[4-(3-fluoropropyloxy)benzoyl]pyrrolidin-2-one

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: trimethylsilyl iodide / chloroform / 18 h / 50 °C
2: caesium carbonate / N,N-dimethyl-formamide / 16 h / 70 °C / Inert atmosphere
View Scheme
aniracetam
72432-10-1

aniracetam

N-[4-(4-fluorobutyloxy)benzoyl]pyrrolidin-2-one

N-[4-(4-fluorobutyloxy)benzoyl]pyrrolidin-2-one

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: trimethylsilyl iodide / chloroform / 18 h / 50 °C
2: caesium carbonate / N,N-dimethyl-formamide / 16 h / 70 °C / Inert atmosphere
View Scheme

Aniracetam Specification

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 %.

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.

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