33643-47-9

Usage

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

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

Downstream Products

• 100477-72-3 (S)-ketamine 

Relevant academic research and scientific papers

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.

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.

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.

(S)-CSA SALT OF S-KETAMINE, (R)-CSA SALT OF S-KETAMINE AND PROCESSES FOR THE PREPARATION OF S-KETAMINE

The present invention is directed to processes for the preparation of esketamine. The present invention is further directed to processes for the resolution of S-ketamine from a racemic or enantiomerically enriched mixture of ketamine. The present invention is further directed to an (S)-CSA salt of S-ketamine, more particularly a monohydrate form of the (S)-CSA salt of S-ketamine; and to an (R)-CSA salt of R-ketamine.

Application Of R-ketamine And Salt Thereof As Pharmaceuticals

Provided is a novel compound having rapid and long-lasting therapeutic effects on diseases exhibiting depressive symptoms. Specifically, provided are an agent for prevention and/or treatment of a depressive symptom, consisting of R(?)-ketamine or a pharmacologically acceptable salt thereof, and a pharmaceutical composition for prevention and/or treatment of a depressive symptom, comprising R(?)-ketamine or a pharmacologically acceptable salt thereof in an effective amount for reducing a depressive symptom, and being substantially free of S(+)-ketamine, and a pharmacologically acceptable salt thereof.

Enantioselective construction of nitrogen-substituted quaternary carbon centers adjacent to the carbonyl group in the cyclohexane ring: first asymmetric synthesis of anesthetic (S)-ketamine with high selectivity

Enantioselective construction of nitrogen-substituted quaternary carbon centers adjacent to the carbonyl group in the cyclohexane ring was performed with respect to the asymmetric synthesis of anesthetic (S)-ketamine 1. Diastereoselective nucleophilic 1,2