176721-04-3

Basic information

• Product Name: (S)-dexmedetomidine-L-(+)-tartrate
• Synonyms: (S)-dexmedetomidine-L-(+)-tartrate
• CAS NO: 176721-04-3
• Molecular Weight: 350.371
• Mol File: 176721-04-3.mol
• Article Data: 8

Chemical Properties

• CAS DataBase Reference: (S)-dexmedetomidine-L-(+)-tartrate(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-dexmedetomidine-L-(+)-tartrate(176721-04-3)
• EPA Substance Registry System: (S)-dexmedetomidine-L-(+)-tartrate(176721-04-3)

Safety Data

• Hazardous Substances Data: 176721-04-3(Hazardous Substances Data)

Usage

Description

(S)-dexmedetomidine-L-(+)-tartrate, also known as Dexmedetomidine (D299000), is an α2-Adrenergic agonist and the (+)-isomer of Medetomidine. It is a sedative and analgesic agent derived from 2,3-Dimethylbenzaldehyde (D464000), which is the major component of the umbel rays oil. (S)-dexmedetomidine-L-(+)-tartrate is characterized by its ability to bind to α2-adrenergic receptors, leading to a range of therapeutic effects.

Uses

Used in Pharmaceutical Industry:
(S)-dexmedetomidine-L-(+)-tartrate is used as a sedative and analgesic agent for its ability to induce sedation and provide pain relief. It is particularly useful in medical and veterinary applications where a controlled level of sedation and analgesia is required.
Used in Anesthesia:
In the field of anesthesia, (S)-dexmedetomidine-L-(+)-tartrate is used as an adjunct to general anesthesia to provide a calm and cooperative patient, reduce the need for additional anesthetic agents, and maintain hemodynamic stability during surgery.
Used in Intensive Care Units (ICUs):
(S)-dexmedetomidine-L-(+)-tartrate is used in ICU settings to provide light to moderate sedation for patients who require mechanical ventilation or are undergoing critical care procedures.
Used in Pain Management:
(S)-dexmedetomidine-L-(+)-tartrate is also used in pain management, particularly for postoperative pain relief and in patients with chronic pain conditions, due to its analgesic properties and ability to reduce the need for opioids.
Used as an Impurity in Dexmedetomidine Production:
(S)-dexmedetomidine-L-(+)-tartrate is recognized as an impurity in the production of Dexmedetomidine, which is important for quality control and ensuring the safety and efficacy of the final product.

Upstream product

• 147-71-7 D-tartaric acid 
• 86347-14-0 medetomidine 
• 767-87-3 1-ethynyl-2,3-dimethylbenzene 
• 176721-02-1 4-<(2,3-dimethylphenyl)carbonyl>-1-(triphenylmethyl)imidazole 
• 176721-01-0 4-<(2,3-dimethylphenyl)hydroxymethyl>-1-(triphenylmethyl)imidazole 
• 1021949-47-2 1-(4-imidazolyl)-1-(2,3-dimethylphenyl)ethylene 
• 87-69-4 L-Tartaric acid 
• 40243-75-2 2,3-dimethylstyrene 
• 61985-25-9 1-(1H-imidazol-4-yl)ethan-1-one 
• 576-23-8 2,3-dimethylbromobenzene 
• 850716-46-0 tert-butyl 4-acetyl-1H-imidazole-1-carboxylate 
• 176721-03-2 4-<1-(2,3-dimethylphenyl)-1-hydroxyethyl>-1-(triphenylmethyl)imidazole 
• 5779-93-1 2,3-dimethylbenzaldehyde 
• 60907-90-6 1-(2,3-dimethylphenyl)ethanol 

Downstream Products

• 113775-47-6 dexmedetomidine 
• 145108-58-3 (-)-(R)-4-(1-[2,3-dimethylphenyl]ethyl)-1H-imidazole hydrochloride 

Relevant articles and documents

METHOD FOR PREPARING DEXMEDETOMIDINE

The present invention relates to a method for preparing dexmedetomidine having the following formula (I): or a pharmaceutically acceptable salt and/or solvate thereof, comprising the following successive steps: a) asymmetric hydrogenation of a methylene derivative of the following formula (II): in order to obtain dexmedetomidine, and b) optionally salifying and/or solvating dexmedetomidine in order to obtain a pharmaceutically acceptable salt and/or solvate of dexmedetomidine, wherein the methylene derivative of formula (II) is prepared from a halide of the following formula (V), in which Hal2 represents a halogen atom such as Br, and a cyanoimidazole of the following formula (VI):. The present invention relates also to methods for preparing synthesis intermediates of dexmedetomidine from the halide of formula (V) and the cyanoimidazole of formula (VI), these synthesis intermediates being the methylene derivative of formula (II), an alcohol of the following formula (III), and a ketone of the following formula (IV):.

Preparation method of dexmedetomidine hydrochloride and its intermediate

The invention discloses a preparation method of dexmedetomidine hydrochloride and its intermediate. A preparation method of dexmedetomidine L-tartrate comprises the steps of subjecting dexmedetomidineintermediate III and hydrogen to reduction reaction in an organic solvent in the presence of a chiral catalyst, and subjecting the reduced product and tartaric acid to neutralization reaction to obtain dexmedetomidine L-tartrate II, wherein the chiral catalyst is (+)-1,2-bis(2S-5S)-diethylphospholano-benzene(1,5-cyclooctadiene)rhodium trifluoromethanesulfonate. The preparation method herein has ashort step path, has no need for chiral splitting, and has high total molar yield; the product prepared herein has high purity, reaches the standard for bulk pharmaceutical chemicals and is suitablefor industrial production.

Method for preparing dexmedetomidine hydrochloride for anesthesia and sedation during operation

The invention discloses a method for preparing dexmedetomidine hydrochloride for anesthesia and sedation during an operation. The method comprises the following steps: (a) stirring and reacting 2,3-dimethyl styrene and imidazole in ionic liquid to obtain 4-[1-(2,3-dimethylphenyl)ethyl]-1H-imidazole in the presence of an iron salt; (b) reacting the 4-[1-(2,3-dimethylphenyl)ethyl]-1H-imidazole with L-(+)-tartaric acid, and performing suction filtering to obtain dexmedetomidine tartrate; (c) stirring the dexmedetomidine tartrate in an aqueous solution of sodium hydroxide, performing dichloromethane extraction and concentration, and stirring in a saturated hydrochloric acid methanol solution to obtain the dexmedetomidine hydrochloride. According to the method, the ionic liquid is used for alkylation reaction of the imidazole under catalysis of the iron salt, so that the reaction time is effectively shortened, and high yield is achieved; fewer steps are required, and the cost is lower; conditions in each step are mild, use of a large amount of lewis acid is avoided, and easiness for industrial production is achieved.