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HomeProduct name listMeclizine dihydrochloride

Meclizine dihydrochloride

Synonym(s):1-([4-Chlorophenyl]phenylmethyl)-4-([3-methylphenyl]methyl)piperazine;1-(p-Chloro-α-phenylbenzyl)-4-(m-methylbenzyl)-piperazine dihydrochloride;1-[(4-Chlorophenyl)phenylmethyl]4-[?(3-methylphenyl)methyl]piperazine dihydrochloride;Meclizine dihydrochloride;NSC 28728

  • CAS NO.:1104-22-9
  • Empirical Formula: C25H29Cl3N2
  • Molecular Weight: 463.87
  • MDL number: MFCD00058199
  • EINECS: 214-164-8
  • SAFETY DATA SHEET (SDS)
  • Update Date: 2024-12-18 14:15:32
Meclizine dihydrochloride Structural

What is Meclizine dihydrochloride?

Description

Meclizine is a histamine H1 receptor antagonist (Ki = 250 nM). Pretreatment with meclizine (2.5-30 mg/kg, i.p.) reduces ovalbumin-induced mast cell degranulation, edema, and leukocyte influx in rat lung. Formulations containing meclizine have been used in the treatment of motion sickness and vertigo.

Chemical properties

White or yellowish-white, slightly hygroscopic, crystalline powder.

Originator

Antivert,Roerig,US,1957

The Uses of Meclizine dihydrochloride

Meclizine Dihydrochloride is a histamine H1 receptor antagonist with antiemetic properties. Meclizine Dihydrochloride is a research product for neuroscience. This compound may exhibit neuroprotective properties.

The Uses of Meclizine dihydrochloride

Antiemetic;Histamine antagonist

The Uses of Meclizine dihydrochloride

cholinergic, diagnostic aid

What are the applications of Application

Meclizine Dihydrochloride is a histamine H1 receptor antagonist and PXR (pregnane X receptor) agonist

Manufacturing Process

32.3 g of 1-p-chlorobenzhydryl-4-benzyl-piperazine, dissolved in 300 cm3 of alcohol are heated in an autoclave vessel, in the presence of Raney nickel, under a pressure of 100 kg H2, at about 150°C for 6 hours. The catalyst is filtered, the solvent is evaporated and the residue is fractionated under a high vacuum. p-Chlorobenzylhydryl-piperazine (BP 180° to 185°C/1 mm Hg) is isolated with a yield of 75%. Then finely ground NaNH2 is added. The mixture is heated under reflux for 1 hour, the mass is cooled and a molar equivalent of m-methyl benzyl chloride is added.
The solvent is evaporated and the residue is dissolved in chloroform. This solution is washed with a saturated solution of K2CO3 and dried on K2CO3. The solvent is evaporated and the residue is distilled under high vacuum. The product of the condensation distills near 230°C at 2 mm Hg pressure and the corresponding dihydrochloride melts at 217° to 224°C.

brand name

Antivert (Pfizer).

Therapeutic Function

Antinauseant

Biochem/physiol Actions

Meclizine has the ability to increase glycolysis and decrease cellular ATP levels in media that has glucose and galactose. It guards the kidney against ischemia-reperfusion injury. Meclizine is considered as an anti-nausea and anti-dizziness drug, was identified in a ′nutrient-sensitized′ chemical screen. In human, it acts as an agonist of pregnane X receptor (PXR). It enhances the expression of CYP3A4 (cytochrome P450 3A4) mRNA and reduces CYP3A-catalyzed testosterone 6β-hydroxylation in primary cultures of human hepatocytes.

Safety Profile

Moderately toxic by ingestion and intraperitoneal routes. An experimental teratogen. Experimental reproductive effects. When heated to decomposition it emits very toxic fumes of Cland NOx.

Solubility in organics

Meclizine dihydrochloride is readily soluble in chloroform and pyridine, slightly soluble in dilute acids and ethanol, and insoluble in water or ether.

storage

Desiccate at RT

Properties of Meclizine dihydrochloride

Melting point: 210.0 to 214.0 °C
storage temp.  2-8°C
solubility  DMSO: soluble5mg/mL, clear (warmed)
form  powder
color  white to beige
CAS DataBase Reference 1104-22-9(CAS DataBase Reference)
EPA Substance Registry System Piperazine, 1-[(4-chlorophenyl)phenylmethyl]-4-[(3-methylphenyl)methyl]-, dihydrochloride (1104-22-9)

Safety information for Meclizine dihydrochloride

Signal word Warning
Pictogram(s)
ghs
Exclamation Mark
Irritant
GHS07
ghs
Health Hazard
GHS08
GHS Hazard Statements H302:Acute toxicity,oral
H361:Reproductive toxicity
Precautionary Statement Codes P201:Obtain special instructions before use.
P308+P313:IF exposed or concerned: Get medical advice/attention.

Computed Descriptors for Meclizine dihydrochloride

Meclizine dihydrochloride manufacturer

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