33643-46-8

Basic information

• Product Name: l-Ketamine
• Synonyms: Cyclohexanone, 2-(2-chlorophenyl)-2-(methylamino)-, (2S)- (9CI);Cyclohexanone, 2-(2-chlorophenyl)-2-(methylamino)-, (S)-;Esketamine;l-Ketamine;(S)-2-(2-Chlorophenyl)-2-(methylamino)cyclohexanone;(S)-2-(Methylamino)-2-(2-chlorophenyl)cyclohexanone;(S)-2-(o-Chlorophenyl)-2-(methylamino)cyclohexanone;Centatin
• CAS NO: 33643-46-8
• Molecular Formula: C13H16ClNO
• Molecular Weight: 237.73
• Product Categories: chemical research;pharmaceutical intermediate
• Mol File: 33643-46-8.mol
• Article Data: 26

Chemical Properties

• Boiling Point: 363.8°Cat760mmHg
• Flash Point: 173.8°C
• Appearance: /
• Density: 1.17g/cm³
• Vapor Pressure: 1.76E-05mmHg at 25°C
• Refractive Index: 1.562
• PKA: 6.46±0.20(Predicted)
• CAS DataBase Reference: l-Ketamine(CAS DataBase Reference)
• NIST Chemistry Reference: l-Ketamine(33643-46-8)
• EPA Substance Registry System: l-Ketamine(33643-46-8)

Safety Data

• Hazardous Substances Data: 33643-46-8(Hazardous Substances Data)

Usage

Definition

ChEBI: The S- (more active) enantiomer of ketamine.

InChI:InChI=1/C13H16ClNO/c1-15-13(9-5-4-8-12(13)16)10-6-2-3-7-11(10)14/h2-3,6-7,15H,4-5,8-9H2,1H3/t13-/m0/s1

Upstream product

• 86144-35-6 DL-N-Nitrosoketamin 
• 67-56-1 methanol 
• 35211-10-0 norketamine 
• 694-80-4 2-bromo-1-chlorobenzene 
• 286-20-4 cyclohexane-1,2-epoxide 
• 74-89-5 methylamine 
• 33795-24-3 (+)-Ketamine hydrochloride 
• 1207986-37-5 (1R,2E)-2-(3-benzyloxypropylidene)-1-(2-chlorophenyl)-1-methylaminocyclohexane 
• 6740-88-1 ketamine 
• 100477-72-3 (+)-Ketamine 
• 147-71-7 D-tartaric acid 
• 3900-89-8 2-Chlorobenzeneboronic acid 
• 873-32-5 2-Chlorobenzonitrile 
• 6740-85-8 (2-chlorophenyl)(cyclopentyl)methanone 

Downstream Products

• 1416850-28-6 2-(2-chloro-phenyl)-2-methylamino-cyclohexanone O-benzyl-oxime 
• 33795-24-3 (+)-Ketamine hydrochloride 
• 100477-72-3 (S)-ketamine 
• 120199-64-6 (2S,6S)-2-amino-2-(2-chlorophenyl)-6-hydroxycyclohexan-1-one 

Relevant articles and documents

LONG-ACTING INJECTABLE FORMULATIONS OF KETAMINE PAMOATE SALTS

Provided are sustained-release pharmaceutical compositions including a ketamine pamoate salt and a pharmaceutically acceptable carrier thereof. The compositions include aqueous suspension, solution and matrix delivery system, which can provide sustained release for anesthesia, analgesia or treatment of central nervous system and anti-inflammatory diseases.

Racemization method of ketamine and derivative or salt thereof

The invention discloses a racemization method of ketamine and a derivative or salt thereof. The racemization method comprises the following step: in a solvent, under the action of a catalyst and at the reaction temperature of 110-200 DEG C, carrying out a

Process Research and Impurity Control Strategy of Esketamine

An improved synthesis of (S)-ketamine (esketamine) has been developed, which was cost-effective, and the undesired isomer could be recovered by racemization. Critical process parameters of each step were identified as well as the process-related impurities. The formation mechanisms and control strategies of most impurities were first discussed. Moreover, the (S)-ketamine tartrate is a dihydrate, which was disclosed for the first time. The practicable racemization catalyzed by aluminum chloride was carried out in quantitative yield with 99% purity. The ICH-grade quality (S)-ketamine hydrochloride was obtained in 51.1% overall yield (14.0% without racemization) by chiral resolution with three times recycling of the mother liquors. The robust process of esketamine could be industrially scalable.