33643-47-9

Basic information

• Product Name: (+)-KETAMINE
• Synonyms: (+)-KETAMINE;(2S)-2-(2-Chlorophenyl)-2-(MethylaMino)cyclohexanone Hydrochloride;Ketanest S;Cyclohexanone,2-(2-chlorophenyl)-2-(MethylaMino)-, hydrochloride (1:1), (2S)-;VCMGMSHEPQENPE-ZOWNYOTGSA-N
• CAS NO: 33643-47-9
• Molecular Formula: C₁₃H₁₆ClNO*ClH
• Molecular Weight: 237.73
• Mol File: 33643-47-9.mol
• Article Data: 8

Chemical Properties

• Appearance: /
• Storage Temp.: 2-8°C
• CAS DataBase Reference: (+)-KETAMINE(CAS DataBase Reference)
• NIST Chemistry Reference: (+)-KETAMINE(33643-47-9)
• EPA Substance Registry System: (+)-KETAMINE(33643-47-9)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 33643-47-9(Hazardous Substances Data)

Usage

Description

(+)-KETAMINE, also known as (S)-Ketamine hydrochloride, is an arylcyclohexylamine that serves as a dissociative anesthetic. It has been utilized both medically and recreationally, and is regulated as a Schedule III compound in the United States. (+)-KETAMINE is primarily intended for research and forensic applications.

Uses

Used in Medical Applications:
(+)-KETAMINE is used as an anesthetic for its dissociative properties, which provide pain relief and sedation during medical procedures. It is particularly effective in managing pain and is often used in situations where other anesthetics may not be suitable or available.
Used in Research Applications:
In the field of research, (+)-KETAMINE is used as an analytical reference material to study its effects on the central nervous system and to develop a better understanding of its mechanisms of action. This research can lead to the development of new therapeutic approaches and treatments for various medical conditions.
Used in Forensic Applications:
(+)-KETAMINE is utilized in forensic science to analyze and identify the presence of the compound in biological samples, such as blood or urine. This is crucial in cases where the substance may have been abused or involved in criminal activities.
Used in Recreational Settings:
Although not a primary application, (+)-KETAMINE has been known to be abused recreationally for its dissociative and hallucinogenic effects. However, it is important to note that the recreational use of this substance is illegal and can lead to serious health risks and legal consequences.

Biochem/physiol Actions

Selective NMDA glutamate receptor antagonist.

Upstream product

• 6740-85-8 (2-chlorophenyl)(cyclopentyl)methanone 
• 33795-24-3 (+)-Ketamine hydrochloride 
• 100477-72-3 (+)-Ketamine 
• 6740-88-1 ketamine 
• 100477-72-3 (S)-ketamine 
• 1867-66-9 (+/-)-ketamine hydrochloride 
• 1174527-56-0 (R)-1-(2-chlorophenyl)-2-ethylidene-1-methylaminocyclohexane 
• 87-69-4 L-Tartaric acid 

Downstream Products

• 100477-72-3 (S)-ketamine 

Relevant articles and documents

Lewis Acid-Catalyzed Racemization and Recycling of the Undesired (R)-Ketamine

The first detailed description of the Lewis acid-catalyzed racemization of (R)-ketamine is reported. A process for racemization of the undesired (R)-ketamine enantiomer produced from the resolution for preparing the NMDA receptor antagonist (S)-ketamine was developed in quantitative yield with 99% chemical purity in the presence of a Lewis acid at 150 °C. Varying degrees of racemization were observed in the presence of various frequently used Lewis acids separately, and the catalytic efficiencies were arranged as follows: MgCl2 ≈ AlCl3 > FeCl3 > ZnCl2 > BF3 > CaCl2. The racemized ketamine was subsequently resolved using l-(+)-tartaric acid to obtain (S)-ketamine in 41% yield with 99.5% ee. Such a concise and cost-efficient approach for the racemization can be industrially useful to recycle the waste (R)-ketamine enantiomer into the resolution process to obtain (S)-ketamine.

Process for (S)-Ketamine and (S)-Norketamine via Resolution Combined with Racemization

A concise, recyclable, and efficient process is presented for the preparation of (S)-ketamine (esketamine, (S)-1a) via classic resolution combined with the recycling of the undesired isomer. With commercially available ketone 2 as the starting material, this procedure features three steps including (1) an unique hydroxylation-ring expansion rearrangement, (2) mild amination via methanesulfonate, and (3) chiral separation using L-(+)-tartaric acid. The three simple steps are all performed in mild conditions and (S)-1a tartrate is obtained in 99.5percent ee without recrystallization. Subsequently, racemization of the unwanted (R)-1a remained in resolution mother liquor was performed in the presence of a Lewis acid in quantitative yield with >99.0percent chemical purity. This original and economical process afforded esketamine in 67.4percent (28.9percent without racemization) overall yield with two times recycling of the mother liquor without column purification. In addition, this procedure can also be applied to the preparation of (S)-norketamine, which is a safer potential antidepressant.

KETAMINE PAMOATE AND USE THEREOF

Provided are pamoate salts of ketamine having a stoichiometry of 2: 1 of ketamine to pamoate, including R, S-ketamine pamoate, S-ketamine pamoate, or R-ketamine pamoate, and crystalline or amorphous forms of the pamoate salts, and having excellent safety and properties for pharmaceutical applications. Also provided are pharmaceutical compositions including the pamoate salts of ketamine and their uses in treating a CNS disease or serving as an anesthetic.