145108-58-3 Usage
Description
4-((S)-alpha,2,3-Trimethylbenzyl)imidazole monohydrochloride, also known as Dexmedetomidine hydrochloride, is an imidazole derivative and the (S)-enantiomer of medetomidine. It is a highly selective and potent α2-adrenoceptor agonist with various pharmacological properties, including sedative, anxiolytic, analgesic, bradycardic, hypotensive, and hypothermic effects. Dexmedetomidine is unique among sedatives as it allows for easily arousable sedation and minimal respiratory depression.
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.
Check Digit Verification of cas no
The CAS Registry Mumber 145108-58-3 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 1,4,5,1,0 and 8 respectively; the second part has 2 digits, 5 and 8 respectively.
Calculate Digit Verification of CAS Registry Number 145108-58:
(8*1)+(7*4)+(6*5)+(5*1)+(4*0)+(3*8)+(2*5)+(1*8)=113
113 % 10 = 3
So 145108-58-3 is a valid CAS Registry Number.
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
145108-58-3Relevant articles and documents
Preparation method of dexmedetomidine hydrochloride
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, (2020/06/20)
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.
Industrial preparation method of dexmedetomidine hydrochloride
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, (2017/08/28)
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.
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