1104-22-9

Basic information

• Product Name: Meclizine dihydrochloride
• Synonyms: MECLIZINE DIHYDROCHLORIDE;1-([4-CHLOROPHENYL]PHENYLMETHYL)-4-([3-METHYLPHENYL]-METHYL)PIPERAZINE DIHYDROCHLORIDE;1-((4-chlorophenyl)phenylmethyl)-4-((3-methylphenyl)methyl)-piperazindih;1-(p-chloro-alpha-phenylbenzyl)-4-(m-methylbenzyl)-piperazindihydrochlorid;1-[(4-chlorophenyl)phenylmethyl]-4-[(3-methylphenyl)methyl]-piperazindihyd;Piperazine, 1-[(4-chlorophenyl)phenylmethyl]-4-[(3-methylphenyl)methyl]-, dihydrochloride (9CI);Postafene dihydrochloride;Piperazine, 1-(p-chloro-.alpha.-phenylbenzyl)-4-(m-methylbenzyl)-, dihydrochloride
• CAS NO: 1104-22-9
• Molecular Formula: C₂₅H₂₇ClN₂*2ClH
• Molecular Weight: 463.87
• EINECS: 214-164-8
• Product Categories: PROVOCHOLINE
• Mol File: 1104-22-9.mol
• Article Data: 1

Chemical Properties

• Melting Point: 210.0 to 214.0 °C
• Boiling Point: 495.3 °C at 760 mmHg
• Flash Point: 253.3 °C
• Appearance: white to beige/
• Density: 1.159g/cm3
• Vapor Pressure: 6E-10mmHg at 25°C
• Storage Temp.: 2-8°C
• Solubility: DMSO: soluble5mg/mL, clear (warmed)
• CAS DataBase Reference: Meclizine dihydrochloride(CAS DataBase Reference)
• NIST Chemistry Reference: Meclizine dihydrochloride(1104-22-9)
• EPA Substance Registry System: Meclizine dihydrochloride(1104-22-9)

Safety Data

• Hazard Codes: Xn
• Statements: 22-63
• Safety Statements: 22-36
• WGK Germany: 3
• RTECS: TL2005000
• Hazardous Substances Data: 1104-22-9(Hazardous Substances Data)

Usage

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

Different sources of media describe the Uses of 1104-22-9 differently. You can refer to the following data:
1. 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.
2. Antiemetic;Histamine antagonist
3. 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.

InChI:InChI=1/C25H27ClN2.ClH/c1-20-6-5-7-21(18-20)19-27-14-16-28(17-15-27)25(22-8-3-2-4-9-22)23-10-12-24(26)13-11-23;/h2-13,18,25H,14-17,19H2,1H3;1H

Upstream product

• 620-19-9 1-chloromethyl-3-methyl-benzene 
• 303-26-4 N-(4-chlorobenzhydryl)piperazine 

Downstream Products

• 163837-33-0 (R)-1-((4-chlorophenyl)(phenyl)methyl)-4-(3-methylbenzyl)piperazine dihydrochloride 
• 163837-33-0 (S)-1-((4-chlorophenyl)(phenyl)methyl)-4-(3-methylbenzyl)piperazine dihydrochloride 
• 163837-49-8 C₂₅H₂₇ClN₂ 
• 163837-49-8 C₂₅H₂₇ClN₂ 
• 163837-33-0 C₂₅H₂₇ClN₂*ClH 
• 114624-70-3 Meclozin-N,N'-dioxid 

Relevant articles and documents

NOVEL WATER BASED PROCESS FOR THE PREPARATION OF SUBSTITUTED DIPHENYLMETHYL PIPERAZINES

The present invention relates to a novel water based process for the preparation of substituted diphenylmethyl piperazines of Formula I and pharmaceutically acceptable salts wherein X1 and X2 represent independently a hydrogen, a halogen, a straight or branched chain lower alkyl, alkoxy or a hydroxyl radical and R is selected from groups such as acyl, alkyl, alkenyl, aralalkyl, aralalkenyl aralkyl, and aralalkenyl or aralkenyl hydroxyalkyl, aryloxyalkyl, alkoxyalkyl, aminoalkyl or its derivative comprising, reacting a compound of Formula II, with a compound of formula R—X where R is as defined above and X is suitable leaving group which includes halides, but not limiting use of other leaving groups such as tosylate, mesylate and activated acid groups such as acyl halide, anhydrides, mixed anhydrides etc. using water as a solvent, in presence of a catalyst and a base, at 25-100° C.;