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Home> Encyclopedia >   /  Pharmaceutical Intermediates  /  Pharmaceutical  /  Pharmaceuticals and Biochemicals  /  Others  /  Organic Intermediate
Aniracetam structure
Aniracetam structure

Aniracetam

Iupac Name:1-(4-methoxybenzoyl)pyrrolidin-2-one
CAS No.:72432-10-1
Molecular Weight:219.24
Introduction:

Cognition enhancer related to Piracetam. Nootropic.

1. Names and Identifiers
1.1 Name
Aniracetam
1.2 Synonyms

1-(4-methoxybenzoyl)-2-pyrrolidinon 1-(4-Methoxybenzoyl)-2-pyrrolidinone 1-(4-Methoxybenzoyl)-2-pyrrolidone 1-(p-methoxybenzoyl)-2-pyrrolidinon 1-p-anisoyl-2-pyrrolidinone AMpaMet Aniracetam Aniracetam Aniracetam, >=99% anixiku Ro 13-3057

1.3 CAS No.
72432-10-1
1.4 CID
2196
1.5 EINECS(EC#)
615-758-3
1.6 Molecular Formula
C12H13NO3 (isomer)
1.7 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
1.8 InChkey
ZXNRTKGTQJPIJK-UHFFFAOYSA-N
1.9 Canonical Smiles
COC1=CC=C(C=C1)C(=O)N2CCCC2=O
1.10 Isomers Smiles
COC1=CC=C(C=C1)C(=O)N2CCCC2=O
2. Properties
3.1 Density
1.236
3.2 Melting Point
119-122oC
3.3 Boiling Point
399.7oC at 760 mmHg
3.4 Refractive Index
1.573
3.5 Flash Point
195.5 oC
3.6 Appearance
White Crystalline or Crystalline Powde
3.7 pKa
-1.74±0.20(Predicted)
3.8 Stability
Stable at normal temperatures and pressures.
3.9 StorageTemp
Keep container tightly closed.
3.10 Water Solubility
3.3 g/L
3. Use and Manufacturing
4.1 Purification Methods
Purify aniracetam by recrystallisation from EtOH. It is a nootropic (Alzheimer) drug. [Gouliaev & Senning Brain Research Rev 19 180 1994.] Aniracetam Preparation Products And Raw materials Raw materials
4.2 Storage
Ambient temperatures.
4.3 Usage

Cognition enhancer related to Piracetam. Nootropic.

4. Safety and Handling
5.1 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.

5.2 Toxicity

CHEMICAL IDENTIFICATION

RTECS NUMBER :
UY5781900
CHEMICAL NAME :
2-Pyrrolidinone, 1-(4-methoxybenzoyl)-
CAS REGISTRY NUMBER :
72432-10-1
LAST UPDATED :
199806
DATA ITEMS CITED :
10
MOLECULAR FORMULA :
C12-H13-N-O3
MOLECULAR WEIGHT :
219.26

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
4500 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
PSCHDL Psychopharmacology (Berlin). (Springer-Verlag New York, Inc., Service Center, 44 Hartz Way, Secaucus, NJ 07094) V.47- 1976- Volume(issue)/page/year: 78,104,1982
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
1255 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
MDACAP Medicamentos de Actualidad. (J.R. Prous, S.A., Apartado de Correos 540, 08080 Barcelona, Spain) V.1- 1965- Volume(issue)/page/year: 30,9,1994
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Subcutaneous
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
>5 gm/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
NIIRDN Drugs in Japan (Ethical Drugs). (Yakugyo Jiho Co., Ltd., Tokyo, Japan) Volume(issue)/page/year: -,45,1995
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
>50 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
MDACAP Medicamentos de Actualidad. (J.R. Prous, S.A., Apartado de Correos 540, 08080 Barcelona, Spain) V.1- 1965- Volume(issue)/page/year: 30,9,1994
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
3648 mg/kg
TOXIC EFFECTS :
Behavioral - somnolence (general depressed activity) Behavioral - convulsions or effect on seizure threshold Gastrointestinal - changes in structure or function of salivary glands
REFERENCE :
YACHDS Yakuri to Chiryo. Pharmacology and Therapeutics. (Raifu Saiensu Shuppan K.K., 2-5-13, Yaesu, Chuo-ku, Tokyo 104, Japan) V.1- 1972- Volume(issue)/page/year: 14(Suppl 4),673,1986
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
1180 mg/kg
TOXIC EFFECTS :
Sense Organs and Special Senses (Eye) - lacrimation Behavioral - somnolence (general depressed activity) Behavioral - convulsions or effect on seizure threshold
REFERENCE :
YACHDS Yakuri to Chiryo. Pharmacology and Therapeutics. (Raifu Saiensu Shuppan K.K., 2-5-13, Yaesu, Chuo-ku, Tokyo 104, Japan) V.1- 1972- Volume(issue)/page/year: 14(Suppl 4),673,1986
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Subcutaneous
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
>5 gm/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
NIIRDN Drugs in Japan (Ethical Drugs). (Yakugyo Jiho Co., Ltd., Tokyo, Japan) Volume(issue)/page/year: -,45,1995
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
>100 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
MDACAP Medicamentos de Actualidad. (J.R. Prous, S.A., Apartado de Correos 540, 08080 Barcelona, Spain) V.1- 1965- Volume(issue)/page/year: 30,9,1994
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rabbit
DOSE/DURATION :
>2 gm/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
MDACAP Medicamentos de Actualidad. (J.R. Prous, S.A., Apartado de Correos 540, 08080 Barcelona, Spain) V.1- 1965- Volume(issue)/page/year: 30,9,1994 ** REPRODUCTIVE DATA **
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
26400 mg/kg
SEX/DURATION :
female 7-17 day(s) after conception
TOXIC EFFECTS :
Reproductive - Maternal Effects - other effects Reproductive - Effects on Embryo or Fetus - fetotoxicity (except death, e.g., stunted fetus) Reproductive - Specific Developmental Abnormalities - musculoskeletal system
REFERENCE :
YACHDS Yakuri to Chiryo. Pharmacology and Therapeutics. (Raifu Saiensu Shuppan K.K., 2-5-13, Yaesu, Chuo-ku, Tokyo 104, Japan) V.1- 1972- Volume(issue)/page/year: 14(Suppl 4),691,1986
5. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

Reproductive toxicity, Category 2

2.2 GHS label elements, including precautionary statements

Pictogram(s)
Signal word

Warning

Hazard statement(s)

H361 Suspected of damaging fertility or the unborn child

Precautionary statement(s)
Prevention

P201 Obtain special instructions before use.

P202 Do not handle until all safety precautions have been read and understood.

P280 Wear protective gloves/protective clothing/eye protection/face protection.

Response

P308+P313 IF exposed or concerned: Get medical advice/ attention.

Storage

P405 Store locked up.

Disposal

P501 Dispose of contents/container to ...

2.3 Other hazards which do not result in classification

none

9. Computational chemical data
  • Molecular Weight:219.24g/mol
  • Molecular Formula:C12H13NO3
  • Compound Is Canonicalized:True
  • XLogP3-AA:
  • Exact Mass:219.08954328
  • Monoisotopic Mass:219.08954328
  • Complexity:282
  • Rotatable Bond Count:2
  • Hydrogen Bond Donor Count:0
  • Hydrogen Bond Acceptor Count:3
  • Topological Polar Surface Area:46.6
  • Heavy Atom Count:16
  • Defined Atom Stereocenter Count:0
  • Undefined Atom Stereocenter Count:0
  • Defined Bond Stereocenter Count:0
  • Undefined Bond Stereocenter Count:0
  • Isotope Atom Count:0
  • Covalently-Bonded Unit Count:1
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