|
| | Meclizine dihydrochloride Basic information |
| Product Name: | Meclizine dihydrochloride | | Synonyms: | Piperazine, 1-[(4-chlorophenyl)phenylmethyl]-4-[(3-methylphenyl)methyl]-, dihydrochloride;Meclozine Hcl;1-((4-Chlorophenyl)(phenyl)Methyl)-4-(3-Methylbenzyl)piperazine dihydrochloride;Meclizine 2HCl;Piperazine,1-[(4-chlorophenyl)phenylMethyl]-4-[(3-Methylphenyl)Methyl]-, hydrochloride(1:2);1-[(4-chlorophenyl)phenylmethyl]-4-[(3-methylphenyl)methyl]-piperazine,hydrochloride (1:2);1-(p-Chloro-α-phenylbenzyl)-4-(m-methylbenzyl)-piperazine dihydrochloride;1-p-chlorbenzhydryl-m-methylbenzylpiperazinedihydrochloride | | CAS: | 1104-22-9 | | MF: | C25H29Cl3N2 | | MW: | 463.87 | | EINECS: | 214-164-8 | | Product Categories: | PROVOCHOLINE | | Mol File: | 1104-22-9.mol |  |
| | Meclizine dihydrochloride Chemical Properties |
| Hazard Codes | Xn | | Risk Statements | 22-63 | | Safety Statements | 22-36 | | WGK Germany | 3 | | RTECS | TL2005000 | | HS Code | 2933.59.8000 | | Toxicity | LD50 oral in mouse: 1600mg/kg |
| | Meclizine dihydrochloride Usage And Synthesis |
| 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 | | Uses | 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. | | Uses | Antiemetic;Histamine antagonist | | Uses | cholinergic, diagnostic aid | | 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. | | storage | Desiccate at RT |
| | Meclizine dihydrochloride Preparation Products And Raw materials |
|
