Introduction：Basic information about Meclizine dihydrochloride CAS 1104-22-9, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.
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
| 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 |
| InChI | 1S/C25H27ClN2.2ClH/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;2*1H |
| InChIKey | VCTHNOIYJIXQLV-UHFFFAOYSA-N |
| SMILES | [Cl-].[Cl-].Clc1ccc(cc1)C(N3CCN(CC3)Cc4cc(ccc4)C)c2ccccc2.[H+].[H+] |
| 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
| Hazard Codes | Xn |
| Risk Statements | 22-63 |
| Safety Statements | 22-36 |
| WGK Germany | 3 |
| RTECS | TL2005000 |
| TSCA | TSCA listed |
| HS Code | 2933.59.8000 |
| Storage Class | 11 - Combustible Solids |
| Hazard Classifications | Acute Tox. 4 Oral
Repr. 2 |
| 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. Thissolution is washed with a saturated solution of K2CO3 and dried on K2CO3. Thesolvent is evaporated and the residue is distilled under high vacuum. Theproduct of the condensation distills near 230°C at 2 mm Hg pressure and thecorresponding 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 |
Meclizine dihydrochloride Preparation Products And Raw materials
| Raw materials | Hydrogen-->3-Methylbenzyl chloride-->Sodium amide |
