Esketamine

Base Information

• Chemical Name: Esketamine
• CAS No.: 33643-46-8
• Molecular Formula: C₁₃H₁₆ClNO
• Molecular Weight: 237.729
• European Community (EC) Number: 811-504-2
• UNII: 50LFG02TXD
• DSSTox Substance ID: DTXSID6047810
• Nikkaji Number: J238.630E
• Wikipedia: Esketamine
• Wikidata: Q2365493
• NCI Thesaurus Code: C81400
• RXCUI: 2119365
• Metabolomics Workbench ID: 61273
• ChEMBL ID: CHEMBL395091
• Mol file: 33643-46-8.mol

Synonyms:(-)-Ketamine;(S)-2-(o-chlorophenyl)-2-(methylamino)cyclohexanone;Esketamine;Kataved;L-Ketamine;S-Ketamine;Spravato

Chemical Property of Esketamine

Chemical Property:

• Vapor Pressure: 1.76E-05mmHg at 25°C
• Boiling Point: 363.8°Cat760mmHg
• PKA: 6.46±0.20(Predicted)
• Flash Point: 173.8°C
• PSA: 29.10000
• Density: 1.17g/cm³
• LogP: 3.28870
• XLogP3: 2.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 237.0920418
• Heavy Atom Count: 16
• Complexity: 269

Purity/Quality:

99.9% ^*data from raw suppliers

ESKETAMINE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Drug Classes: Antidepressant Agents
• Canonical SMILES: CNC1(CCCCC1=O)C2=CC=CC=C2Cl
• Isomeric SMILES: CN[C@@]1(CCCCC1=O)C2=CC=CC=C2Cl
• Recent ClinicalTrials: University of Iowa Interventional Psychiatry Service Patient Registry
• Recent EU Clinical Trials: S-ketamine for cortical spreading depolarisation in patients with severe acute brain injury
• Recent NIPH Clinical Trials: COMPARATIVE STUDY OF ESKETAMINE AND RACEMIC KETAMINE IN TREATMENT-RESISTANT DEPRESSION: A RANDOMIZED, DOUBLE-BLIND, NON-INFERIORITY TRIAL

Technology Process of Esketamine

There total 72 articles about Esketamine 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: 99.0%

(+/-)-ketamine hydrochloride (1867-66-9) → ketamine (6740-88-1,100477-72-3,33643-46-8,33643-49-1)

Guidance literature:

With sodium hydroxide; In chloroform; water;

Reference yield: 90.0%

formaldehyd (50-00-0,30525-89-4,61233-19-0) + norketamine (35211-10-0,83777-65-5) → ketamine (6740-88-1,100477-72-3,33643-46-8,33643-49-1)

Guidance literature:

With sodium cyanoborohydride; acetic acid; In methanol; at 20 ℃; for 12h;

Reference yield: 85.3%

(±)-2-(2-chlorophenyl)-2-hydroxycyclohexan-1-one + methylamine (74-89-5) → ketamine (6740-88-1,100477-72-3,33643-46-8,33643-49-1)

Guidance literature:

(±)-2-(2-chlorophenyl)-2-hydroxycyclohexan-1-one; With methanesulfonyl chloride; triethylamine; In tetrahydrofuran; at -5 - 0 ℃; for 1h; Inert atmosphere;

methylamine; In ethanol; at 15 - 20 ℃;

DOI:10.1021/acs.joc.0c01090

upstream raw materials:

DL-N-Nitrosoketamin

(+/-)-ketamine hydrochloride

2-(2-chlorophenyl)-2-nitrocyclohexan-1-one

formaldehyd

Downstream raw materials:

(+)-Ketamine hydrochloride

(S)-ketamine

(2S,6S)-2-amino-2-(2-chlorophenyl)-6-hydroxycyclohexan-1-one

Refernces

• 1、 -. "Cycloalkyl-Diamines for the Treatment of Pain". Paragraph 0175-0180. . Retrieved 2021/02/26.
• 2、 Gao, Shenghua,Gao, Xuezhi,Yang, Zhezhou,Zhang, Fuli. "Process Research and Impurity Control Strategy of Esketamine". . p. 555 - 566. Retrieved 2020/05/19.