145108-58-3

Basic information

• Product Name: 4-((S)-alpha,2,3-Trimethylbenzyl)imidazole monohydrochloride
• Synonyms: 4-[(1r)-1-(2,3-dimethylphenyl)ethyl]-3h-imidazole hydrochloride;4-((s)-alpha,2,3-trimethylbenzyl)imidazole monohydrochloride;DEXMEDETOMIDINE HCL;DEXMEDETOMIDINE HYDROCHLORIDE;DEMEDETOMIDINE HCL;Dexmedetomidine(Pilot);4-[(1S)-1-(2,3-Dimethylphenyl)ethyl]-1H-imidazolehydrochloride;4-((S)-α,2,3-Trimethylbenzyl)imidazole monohydrochloride
• CAS NO: 145108-58-3
• Molecular Formula: C13H17ClN2
• Molecular Weight: 236.74048
• EINECS: 1806241-263-5
• Product Categories: Inhibitors
• Mol File: 145108-58-3.mol

Chemical Properties

• Melting Point: 156.5-157.5°
• Boiling Point: 381.9 ºC at 760 mmHg
• Flash Point: 191.3 ºC
• Appearance: white to beige/
• Density: 1.17 g/cm3
• Vapor Pressure: 1.08E-05mmHg at 25°C
• Storage Temp.: Desiccate at RT
• Solubility: H2O: soluble20mg/mL, clear
• Merck: 14,2946
• CAS DataBase Reference: 4-((S)-alpha,2,3-Trimethylbenzyl)imidazole monohydrochloride(CAS DataBase Reference)
• NIST Chemistry Reference: 4-((S)-alpha,2,3-Trimethylbenzyl)imidazole monohydrochloride(145108-58-3)
• EPA Substance Registry System: 4-((S)-alpha,2,3-Trimethylbenzyl)imidazole monohydrochloride(145108-58-3)

Safety Data

• Hazard Codes: Xn
• Statements: 22-36/37/38
• Safety Statements: 26-36/37/39
• WGK Germany: 3
• RTECS: NI5156750
• Hazardous Substances Data: 145108-58-3(Hazardous Substances Data)

Usage

Uses

Used in Intensive Care Unit Sedation:
4-((S)-alpha,2,3-Trimethylbenzyl)imidazole monohydrochloride is used as a sedative agent for initially intubated and mechanically ventilated patients in an intensive care unit. It provides sedation, analgesia, and anxiolysis while allowing patients to be easily awakened, making it a preferred choice over other sedatives like benzodiazepines or opioids.
Used in Cardiovascular Research:
4-((S)-alpha,2,3-Trimethylbenzyl)imidazole monohydrochloride is used as a research tool to study its effects on primary neonatal rat cardiomyocytes under hypoxic/reoxygenation conditions. This helps in understanding the compound's impact on cardiovascular health and its potential applications in treating related conditions.
Used in Respiratory Research:
4-((S)-alpha,2,3-Trimethylbenzyl)imidazole monohydrochloride is used as a research compound to study the effects of dexmedetomidine pretreatment on lipopolysaccharide-induced acute lung injury in mice. This aids in exploring the potential therapeutic applications of the compound in respiratory conditions.
Used in Anesthesia and Analgesia:
4-((S)-alpha,2,3-Trimethylbenzyl)imidazole monohydrochloride is used as an anesthetic and analgesic agent due to its ability to stimulate the a2A subtype receptor, providing sedative, anesthetic, and analgesic effects.
Used in Drug Metabolism and Pharmacokinetics:
4-((S)-alpha,2,3-Trimethylbenzyl)imidazole monohydrochloride is used as a CYP2D6 inhibitor in pharmacological studies, although it is less potent than the clinically relevant standard quinidine. This application helps in understanding the compound's role in drug metabolism and its potential interactions with other medications.
Brand Name:
The brand name for 4-((S)-alpha,2,3-Trimethylbenzyl)imidazole monohydrochloride is Precedex.

Biological Activity

Active isomer of Medetomide (4-[1-(2,3-Dimethylphenyl)ethyl]-1H-imidazolehydrochloride ), a potent, highly selective α 2 -adrenoceptor agonist (K i values are 1.08 and 1750 nM for α 2 - and α 1 -adrenoceptors respectively). Displays greater selectivity over α 1 -adrenoceptors than clonidine and UK 14,304 (1620-, 220- and 300-fold respectively). Active in vivo ; displays hypotensive, bradycardic, sedative, anxiolytic, hypothermic and analgesic effects.

Biochem/physiol Actions

Dexmedetomidine hydrochloride is a highly potent and selective α2-adrenergic agonist with analgesic and sedative properties, the (+)-isomer of medetomidine. Dexmedetomidine hydrochloride is used clinically as an anesthetic agent to reduce anxiety and tension and promote relaxation and sedation without causing respiratory depression.

InChI:InChI=1/C13H16N2.ClH/c1-9-5-4-6-12(10(9)2)11(3)13-7-14-8-15-13;/h4-8,11H,1-3H3,(H,14,15);1H/t11-;/m0./s1

Upstream product

• 60907-90-6 1-(2,3-dimethylphenyl)ethanol 
• 86347-14-0 medetomidine 
• 850716-46-0 tert-butyl 4-acetyl-1H-imidazole-1-carboxylate 
• 176721-03-2 4-<1-(2,3-dimethylphenyl)-1-hydroxyethyl>-1-(triphenylmethyl)imidazole 
• 60907-88-2 1-(1-chloroethyl)-2,3-dimethylbenzene 
• 138867-04-6 1-N,N-Dimethylsulfamoyl-2-(tert-butyldimethylsilyl)-5-(2,3-dimethylbenzoyl)imidazole 

Relevant articles and documents

Preparation method of dexmedetomidine hydrochloride

The invention discloses a preparation method of dexmedetomidine hydrochloride. The method comprises the following steps: taking 2,3-dimethyl-chloroethylbenzene as a raw material, and reacting with magnesium to prepare a Grignard reagent; carrying out addition reaction with formaldehyde to obtain 2-(2, 3-dimethylphenyl) propanol, and carrying out oxidizing through potassium dichromate to obtain 2-(2,3-dimethylphenyl) propionaldehyde; then, reacting with a methanol solution of ammonia gas to obtain imine, performing Van Leusen reaction with p-toluenesulfonylmethyl Isocyanide to obtain medetomidine; and finally, performing tartaric acid chiral resolution to obtain the dexmedetomidine hydrochloride. The method is simple in reaction condition, easy to meet and convenient to operate; and the preparation method is safe and reliable, does not involve high-risk reactions such as alkyl lithium dehydrogenation, catalytic hydrogenation and the like in the prior art, is high in safety coefficient,and has important significance in process safety of the chemical industry where safety production is taken as a first gripper and production accidents happen frequently.

Method for synthesizing dexmedetomidine hydrochloride

The invention belongs to the technical field of drug preparation, and particularly relates to a method for synthesizing dexmedetomidine hydrochloride. The method for synthesizing dexmedetomidine hydrochloride comprises the steps that reaction of 2,3-dimethylbenzoyl chloride and 1-N,N-dimethyl sulfonyl-2-(tert-butyldimethylsily)-5-(2,3-dimethyl benzoyl) imidazole is adopted, reflux is carried out to remove a protecting group under the action of hydrochloric acid, intermediate 4(5)-(2,3-dimethyl benzoyl) imidazole is obtained, lastly, reduction is carried out to obtain medetomidine under the action of monomethylamine, dexmedetomidine is obtained through the resolution of medetomidine under the action of tartaric acid, and lastly, dexmedetomidine is salified with hydrochloric acid to obtain dexmedetomidine hydrochloride. Compared with the prior art, the method for synthesizing dexmedetomidine hydrochloride has the advantages that a synthetic route is shorter, the operation is easy, and astarting material is easy to obtain.

Industrial preparation method of dexmedetomidine hydrochloride

The invention discloses an industrial preparation method of dexmedetomidine hydrochloride, and belongs to the field of medicines. The method comprises the following steps: directly carrying out a Friedel-Crafts alkylation reaction on initial raw materials comprising 1-(2,3-dimethylphenyl)ethanol not subjected to a chlorination (thionyl chloride) reaction and protected imidazole under the catalysis of a Lewis acid to obtain racemic dexmedetomidine, carrying out pre-resolution purification on the racemic dexmedetomidine through a chiral acid, carrying out chiral acid resolution and alkali dissociation, and adding a hydrochloric acid organic solvent to form a salt in order to obtain the dexmedetomidine hydrochloride. The method avoids use of the toxic and corrosive regent thionyl chloride, allows the above product with high chiral and chemical purity to be obtained and the yield to be high, and is suitable for industrial production.

Method for preparing dexmedetomidine and intermediate thereof

The invention provides a method for preparing dexmedetomidine and an intermediate thereof. Specifically speaking, the method comprises the steps that a compound shown as a formula II (please see the formula in the description) reacts with metal magnesium to prepare a metal magnesium Grignard reagent, and then the metal magnesium Grignard reagent reacts with a compound shown as a formula III (please see the formula in the description). The process has the advantages of being few in step, high in yield, easy to operate, high in product purity and the like and is quite suitable for large-scale industrialized production.