Pramiracetam

Base Information

• Chemical Name: Pramiracetam
• CAS No.: 68497-62-1
• Molecular Formula: C14H27N3O2
• Molecular Weight: 269.387
• Hs Code.: 2942000000
• European Community (EC) Number: 806-175-7
• UNII: 4449F8I3LE
• DSSTox Substance ID: DTXSID60218604
• Nikkaji Number: J18.594I
• Wikipedia: Pramiracetam
• Wikidata: Q415746
• NCI Thesaurus Code: C84171
• Metabolomics Workbench ID: 154076
• ChEMBL ID: CHEMBL159776
• Mol file: 68497-62-1.mol

Synonyms:N-(2-(bis(1-methylethyl)amino)ethyl)-2-oxo-1-pyrrolidineacetamide;pramiracetam;pramiracetam hydrochloride;pramiracetam sulfate;Pramistar

Chemical Property of Pramiracetam

Chemical Property:

• Appearance/Colour: white crystalline powder
• Vapor Pressure: 1.11E-08mmHg at 25°C
• Melting Point: 47-48°
• Refractive Index: 1.495
• Boiling Point: 461 °C at 760 mmHg
• PKA: 14.76±0.46(Predicted)
• Flash Point: 232.6 °C
• PSA: 52.65000
• Density: 1.036 g/cm³
• LogP: 1.17260
• Storage Temp.: 2-8°C
• Solubility.: H2O: soluble10mg/mL, clear
• XLogP3: 0.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 7
• Exact Mass: 269.21032711
• Heavy Atom Count: 19
• Complexity: 308

Purity/Quality:

99%, ^*data from raw suppliers

pramiracetam ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)N(CCNC(=O)CN1CCCC1=O)C(C)C
• Description: Pramiracetam as a pyrrolidones cerebral metabolism improving drug,is a kind of CNS drugs that can help improve memory, anti-forgetful , it is developed by the United States Parke-Davis pharmaceutical companies, with a strong improvement in brain function, enhancing memory, the ability to promote brain alertness, and clinical trials have proved that its activity is 6-13 times of piracetam, 3-4 times of oxiracetam, 1.25 times of aniracetam, and it is toxicity low and well tolerated, it can be used for long-term medication to improve symptoms, and delay Alzheimer-type dementia.Clinically relevant for elderly people attention and memory disorders, benign forgetfulness of aging, senile dementia (Alzheimer's disease) prevention, enhancing memory. Pramiracetam also applies to dilate blood vessels bodybuilding health products additives.
• Uses: Pramiracetam is an inhibitor of PREP and anti-migraine agent. It is a more potent nootropic drug derived from piracetam. Pramiracetam reportedly improved cognitive deficits associated with traumatic brain injuries. It was also effective in the treatment of cognitive disorders of cerebrovascular and traumatic origins.

Technology Process of Pramiracetam

There total 6 articles about Pramiracetam which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 89.49%

2-pyrrolidinon (616-45-5) + N-[2-(di(isopropyl)amino)ethyl]-2-chloroacetamide → pramiracetam (68497-62-1)

Guidance literature:

2-pyrrolidinon; With sodium methylate; In toluene; at 105 - 108 ℃; for 3h;

N-[2-(di(isopropyl)amino)ethyl]-2-chloroacetamide; In toluene; at 60 - 70 ℃;

Reference yield: 83.2%

2-pyrrolidinon (616-45-5) + N-(2-diisopropylaminoethyl)chloroacetamide hydrochloride → pramiracetam (68497-62-1)

Guidance literature:

2-pyrrolidinon; With sodium ethanolate; In toluene; at 80 - 105 ℃; Inert atmosphere;

N-(2-diisopropylaminoethyl)chloroacetamide hydrochloride; In toluene; at 40 - 80 ℃;

Reference yield: 69.0%

2-(oxo-pyrrolidin-1-yl)-acetic acid ethyl ester (61516-73-2) + N',N'-diisopropyl-ethane-1,2-diamine (121-05-1) → pramiracetam (68497-62-1)

Guidance literature:

at 100 ℃; for 16h;

DOI:10.1021/jm00371a023

upstream raw materials:

2-(oxo-pyrrolidin-1-yl)-acetic acid ethyl ester

N',N'-diisopropyl-ethane-1,2-diamine

2-pyrrolidinon

Downstream raw materials:

Pramiracetam sulfate

Refernces

• 1、 -. "The preparation method of N, N - diisopropylethylenediamine. Preparation method of". Paragraph 0055; 0129; 0158-0166. . Retrieved 2021/08/25.
• 2、 Cioc, R?zvan C.,Schaepkens van Riempst, Lola,Schuckman, Peter,Ruijter, Eelco,Orru, Romano V. A.. "Ugi Four-Center Three-Component Reaction as a Direct Approach to Racetams". . p. 1664 - 1674. Retrieved 2017/03/21.