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HomeProduct name listDexmedetomidine hydrochloride

Dexmedetomidine hydrochloride

Synonym(s):(+)-Medetomidine hydrochloride;(S)-Medetomidine hydrochloride;4-[(S)-α,2,3-Trimethylbenzyl]imidazole monohydrochloride;5-[(1S)-1-(2,3-Dimethylphenyl)ethyl]-1H-imidazole hydrochloride;Dexmedetomidine hydrochloride

  • CAS NO.:145108-58-3
  • Empirical Formula: C13H17ClN2
  • Molecular Weight: 236.74
  • MDL number: MFCD07772269
  • EINECS: 682-047-2
  • SAFETY DATA SHEET (SDS)
  • Update Date: 2024-11-05 19:05:58
Dexmedetomidine hydrochloride Structural

What is Dexmedetomidine hydrochloride?

Description

Dexmedetomidine was launched in the US as an i.v. infusion for sedation of initially intubated and mechanically ventilated patients during treatment in an intensive care unit, This imidazole derivative is the (S)-enantiomer of medetomidine that can be obtained via fractional crystallization of the tartrate salt of the racemic mixture. Dexmedetomidine is a full agonist of α2 adrenoceptors with 1300-fold selectivity versus α1 compared to the less selective partial α2 agonist clonidine, a veterinary hypnotic. Dexmedetomidine is unique compared with currently available sedatives in that it provides sedation, analgesia and anxiolysis with the ability of patients to be easily awakened. Besides, it causes minimal respiratory depression unlike other available drugs such as benzodiazepines or opioids. Pharmacological studies in transgenic mice showed that the sedative, anesthetic and analgesic effects of dexmedetomidine are specifically due to the stimulation of the a2A subtype receptor. Like other α2 adrenoceptor agonists, dexmedetomidine can provoke hypotension and bradycardia probably because of its non-selective action on peripheral a2B subtype receptors in vascular smooth muscle. Dexmedetomidine is extensively metabolized into methyl and glucuronide conjugates which are mainly eliminated by renal excretion. It was found to be a CYP2D6 inhibitor but less potent than the clinically relevant standard quinidine.

Physical properties

Dexmedetomidine hydrochloride is a white or almost white powder that is freely soluble in water and has a pKa of 7.1.

Originator

Orion (Finland)

The Uses of Dexmedetomidine hydrochloride

Dexmedetomidine hydrochloride has been used to study its effects on primary neonatal rat cardiomyocytes under hypoxic/reoxygenation conditions. It has also been used to study the effects of dexmedetomidine pretreatment on lipopolysaccharide-induced acute lung injury in mice.

The Uses of Dexmedetomidine hydrochloride

highly selective, potent α2-adrenoceptor agonist, analgesic, anxiolytic, bradycardic, hypotensive, sedative, hypothermic

What are the applications of Application

Dexmedetomidine hydrochloride is an active isomer of medetomide, a potent and highly selective α2-adrenoceptor agonist

Definition

ChEBI: Dexmedetomidine hydrochloride is a medetomidine hydrochloride. It has a role as a sedative. It contains a dexmedetomidine. It is an enantiomer of a levomedetomidine hydrochloride.

brand name

Precedex

Benefits

The chemical name of dexmedetomidine hydrochloride is (S) -4- [1- (2,3- 3,5-dimethylphenyl) ethyl] -1H- imidazole hydrochlorides. Dexmedetomidine hydrochloride has an anti-sympathetic town. The effect of quiet and analgesic, compared with U.S. support pyrimidine, with higher selectivity and a short half-life, can be clinically used for Intensive Care Therapy. Start intubation and calmness using a lung ventilator patient during treatment. Meanwhile, the medicine can also reduce narcotic consumption, improve hand incidence of hemodynamic stability, and reduce myocardial ischaemia in art.

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.

Side Effects

Dexmedetomidine hydrochloride may cause serious side effects including: low or high blood pressure,slow heart rate, and abnormal heart rate.

Synthesis

In a 500mL round-bottomed flask, (S)-1 (18.6g, 93mmo1) is dissolved into 50mL dehydrated alcohol, and adding HC1/ ethanolic soln to adjust pH is 2~3, add THF solution 300mL, placement is spent the night, and now adularescent crystallization, filters, crude product is through ethyl acetate/ethyl alcohol recrystallization, filter, infrared drying oven is dried to obtain dexmedetomidine hydrochloride (20.1g, yield 91.5%).

storage

-20°C

Properties of Dexmedetomidine hydrochloride

Melting point: 156.5-157.5°
alpha  +52.4° (c = 1 in water)
Density  1.17 g/cm3
storage temp.  2-8°C
solubility  H2O: soluble20mg/mL, clear
form  powder
color  white to beige
optical activity [α]/D +48 to +58°, c = 1 in H2O
Merck  14,2946
Stability: Hygroscopic
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-;/s3
CAS DataBase Reference 145108-58-3(CAS DataBase Reference)

Safety information for Dexmedetomidine hydrochloride

Signal word Warning
Pictogram(s)
ghs
Exclamation Mark
Irritant
GHS07
GHS Hazard Statements H302:Acute toxicity,oral
H315:Skin corrosion/irritation
H319:Serious eye damage/eye irritation
H335:Specific target organ toxicity, single exposure;Respiratory tract irritation
Precautionary Statement Codes P261:Avoid breathing dust/fume/gas/mist/vapours/spray.
P264:Wash hands thoroughly after handling.
P264:Wash skin thouroughly after handling.
P270:Do not eat, drink or smoke when using this product.
P301+P312:IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P302+P352:IF ON SKIN: wash with plenty of soap and water.
P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

Computed Descriptors for Dexmedetomidine hydrochloride

InChIKey VPNGEIHDPSLNMU-MERQFXBCSA-N
SMILES [C@@H](C1NC=NC=1)(C1C=CC=C(C)C=1C)C.Cl |&1:0,r|

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