116041-13-5

Basic information

• Product Name: NEBRACETAM
• Synonyms: NEBRACETAM;(±)-4-(Aminomethyl)-1-(phenylmethyl)-2-pyrrolidinone;WEB-1881;WEB-1881FU;Nebracetamum;Nebracetamum [inn-latin];Unii-T30038qi8n
• CAS NO: 116041-13-5
• Molecular Formula: C12H16N2O
• Molecular Weight: 204.271
• Mol File: 116041-13-5.mol

Chemical Properties

• Boiling Point: 395.7°C at 760 mmHg
• Flash Point: 193.1°C
• Appearance: /
• Density: 1.139g/cm³
• Vapor Pressure: 1.8E-06mmHg at 25°C
• Refractive Index: 1.578
• CAS DataBase Reference: NEBRACETAM(CAS DataBase Reference)
• NIST Chemistry Reference: NEBRACETAM(116041-13-5)
• EPA Substance Registry System: NEBRACETAM(116041-13-5)

Safety Data

• Hazardous Substances Data: 116041-13-5(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
NEBRACETAM is used as a cognitive enhancer for its potential to improve memory and learning abilities. Its capacity to increase acetylcholine levels in the brain suggests a role in enhancing cognitive processing.
Used in Neuroprotection:
NEBRACETAM is utilized for its neuroprotective properties, which may support and maintain brain health and function, particularly in conditions where cognitive decline is a concern.
Used in Research and Development:
NEBRACETAM serves as a subject of ongoing research to further explore its effects on cognitive enhancement and neuroprotection, with the aim of understanding its full potential and safety profile for future medical applications.

InChI:InChI=1/C12H16N2O/c13-7-11-6-12(15)14(9-11)8-10-4-2-1-3-5-10/h1-5,11H,6-9,13H2

Upstream product

• 64-17-5 ethanol 
• 110-17-8 (2E)-but-2-enedioic acid 
• 617-52-7 Dimethyl itakonate 
• 100-46-9 benzylamine 
• 51535-00-3 methyl 1-benzyl-5-oxo-3-pyrrolidinecarboxylate 
• 1373821-40-9 C₁₃H₁₇NO₄S 
• 1040922-78-8 N-benzyl-(4S)-4-azidomethyl-pyrrolidin-2-one 
• 1092379-91-3 C₁₂H₁₄N₂O₃ 

Downstream Products

• 676627-00-2 5-aminomethylpyrrolidin-2-one 
• 676630-95-8 N-(5-oxo-pyrrolidin-3-ylmethyl)-6-(2,4-dichloro-phenylamino)-4-trifluoromethyl-nicotinamide 

Relevant articles and documents

A method for preparing west Naira Tanzania

The invention discloses a preparation method for nebracetam, and belongs to the technical field of medical chemistry. The key points of the technical scheme of the invention are as follows: the preparation method for the nebracetam comprises the following steps: performing Michael addition reaction and intramolecular cyclization on dimethyl itaconate and benzylamine serving as raw materials to obtain 1-benzyl-5-oxopyrrolidin-3-carboxylic methyl ester; reducing the 1-benzyl-5-oxopyrrolidin-3-carboxylic methyl ester by sodium borohydride to obtain 1-benzyl-4-hydroxymethyl-pyrrolidine-2-keton; performing methyl sulfonylation on the 1-benzyl-4-hydroxymethyl-pyrrolidine-2-keton to obtain 1-benzyl-5-oxopyrrolidin-3-carboxylic methanesulfonate; finally, performing ammonification and reduction on the 1-benzyl-5-oxopyrrolidin-3-carboxylic methanesulfonate by using ammonia water to obtain the nebracetam. The preparation method is simple in preparation process, easy to control and high in target product yield, and meets the requirement for green chemistry.

Chemoenzymatic total synthesis and determination of the absolute configuration of (S)-nebracetam

We have developed an asymmetric total synthesis of nebracetam 3 by a chemoenzymatic strategy. Diastereoselective Michael addition of nitromethane to the chiral lactam (S)-9d (>99% ee), which was prepared by lipase-catalyzed kinetic resolution, afforded the Michael product 10d in 99% yield with 86% de. Chemical transformations of 10d including recrystallization furnished the chiral nebracetam 3 and its derivative. The absolute configuration of the chiral (-)-nebracetam was determined to be an (S)-configuration.

First stereoselective synthesis and assignment of the absolute configuration of the nebracetam eutomer and derivatives

(-)-Nebracetam 1 was stereoselectively prepared for the first time, allowing the determination of its absolute configuration as (R). The pivotal intermediate in the synthesis, 1-benzyl-4-[(S)-2,2-dimethyl-1,3-dioxolan-4-yl]-pyrrolidin-2-one 6, was previously obtained in 60% yield and 90% ee from an enoate derived from d-mannitol. Two approaches were investigated to synthesize (R)-(-)-nebracetam 1 and analogues 4 and 5 from 6. Compound 6 was transformed into WEB-1868 2. Mesylation of the hydroxyl group in 2, followed by nucleophilic substitution with azide and reduction led to target 1. Compounds 4 and 5 were synthesized by using morpholine and N-methyl piperazine as nucleophiles. Compounds 4 and 5 were also prepared, in higher yields and similar ee, through the reductive amination of aldehyde 10, obtained in two steps from 6.

Agent with an antidepressant activity

An improved process for employing tricyclic antidepressants involving co-administration of a N-benzyl-pyrrolidin-2-one.

Agent with an antidepressant activity

An improved process for employing tricyclic antidepressants involving co-administration of a N-benzyl-pyrrolidin-2-one.

Use of 1-benzyl-aminoalkyl-pyrrolidinones as antidepressants

The invention relates to the use of 1-benzyl-aminoalkyl-pyrrolidinones as antidepressants.

Piperazinyl and morpholinyl substituted 1-(benzyl or pyridylmethyl)-4-or-5-aminomethyl-pyrrolidin-2-ones and their nootropic use

Compounds of the formula STR1 wherein R1 is hydrogen or alkyl of 1 to 4 carbon atoms; R2 is 2-, 3- or 4-pyridyl, phenyl or mono- or di- substituted phenyl, where the substituents are each individually alkoxy of 1 to 2 carbon atoms, f