Etiracetam

Base Information

• Chemical Name: Etiracetam
• CAS No.: 33996-58-6
• Deprecated CAS: 103833-73-4
• Molecular Formula: C₈H₁₄N₂O₂
• Molecular Weight: 170.211
• Hs Code.: 2933790002
• European Community (EC) Number: 446-650-2,642-997-0
• UNII: 230447L0GL
• DSSTox Substance ID: DTXSID5046510
• Nikkaji Number: J17.546C
• Wikipedia: Etiracetam
• Wikidata: Q15408406
• NCI Thesaurus Code: C78002
• Metabolomics Workbench ID: 152953
• ChEMBL ID: CHEMBL1400561
• Mol file: 33996-58-6.mol

Synonyms:alpha ethyl 2 oxo 1 Pyrrolidineacetamide;alpha-ethyl-2-oxo-1-pyrrolidineacetamide;etiracetam;Etiracetam, (R)-;Etiracetam, R isomer;etiracetam, R-isomer;Etiracetam, S isomer;etiracetam, S-isomer;Keppra;levetiracetam;R-isomer Etiracetam;S-isomer Etiracetam;UCB 6474;ucb L059;ucb L060;UCB-6474;ucb-L059;ucb-L060;UCB6474;UcbL060

Chemical Property of Etiracetam

Chemical Property:

• Vapor Pressure: 1.78E-06mmHg at 25°C
• Melting Point: 113-114 °C(Solv: acetone (67-64-1))
• Refractive Index: 1.518
• Boiling Point: 395.9 °C at 760 mmHg
• PKA: 15.74±0.50(Predicted)
• Flash Point: 193.2 °C
• PSA: 63.40000
• Density: 1.168 g/cm³
• LogP: 0.51090
• Water Solubility.: 401g/L at 20℃
• XLogP3: -0.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 3
• Exact Mass: 170.105527694
• Heavy Atom Count: 12
• Complexity: 203

Purity/Quality:

99% ^*data from raw suppliers

Etiracetam ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn,N
• Statements: 22-36-51/53
• Safety Statements: 26-61

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCC(C(=O)N)N1CCCC1=O
• Uses: A nootropic drug that produced a significant increase in β-wave activity and stimulated α-wave activity dose-dependently. Etiracetam has been used in studies to alleviate the effects of memory retrieval defic its in rats.

Technology Process of Etiracetam

There total 6 articles about Etiracetam 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: 76.0%

2-(pyrrolidin-1-yl)butanamide → α-ethyl-2-oxo-1-pyrrolidineacetamide (102767-28-2,103765-01-1,103833-73-4,33996-58-6) + C8H16N2O2

Guidance literature:

With sodium periodate; ruthenium(IV) oxide hydrate; In ethyl acetate; at 20 ℃; for 0.5h; Sonication;

Reference yield: 66.0%

α-ethyl-2-oxo-1-pyrrolidineacetic acid, (67118-31-4) → α-ethyl-2-oxo-1-pyrrolidineacetamide (102767-28-2,103765-01-1,103833-73-4,33996-58-6)

Guidance literature:

α-ethyl-2-oxo-1-pyrrolidineacetic acid,; With chloroformic acid ethyl ester; triethylamine; In tetrahydrofuran; at 0 ℃; for 0.5h;

With ammonium hydroxide; In tetrahydrofuran; water; at 20 ℃; for 16h;

DOI:10.1016/j.tetasy.2005.10.014

Reference yield: 17.0%

(S)-(-)-α-ethyl-2-oxo-1-pyrrolidineacetamide → α-ethyl-2-oxo-1-pyrrolidineacetamide (102767-28-2,103765-01-1,103833-73-4,33996-58-6)

Guidance literature:

With sodium hydroxide; Electrochemical reaction;

DOI:10.1039/d0gc03358h

upstream raw materials:

α-ethyl-2-oxo-1-pyrrolidineacetic acid,

levetiracetam

Downstream raw materials:

C₈H₈O₃*C₈H₁₄N₂O₂

Refernces

• 1、 -. "REGIOSELECTIVE OXIDATION OF HETEROCYCLIC ALPHA-AMINO AMIDES". Page/Page column 87-88. . Retrieved 2021/10/30.
• 2、 Shemchuk, Oleksii,Song, Lixing,Robeyns, Koen,Braga, Dario,Grepioni, Fabrizia,Leyssens, Tom. "Solid-state chiral resolution mediated by stoichiometry: Crystallizing etiracetam with ZnCl2". supporting information. p. 10890 - 10892. Retrieved 2018/10/02.