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

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

HS Code 

2933.59.8000

Toxicity

LD50 oral in mouse: 1600mg/kg

MSDS

• Language:English Provider:SigmaAldrich

Meclizine dihydrochloride Usage And Synthesis

Description

Meclizine is a histamine H₁ receptor antagonist (K_i = 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.

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(1104-22-9)Related Product Information

• Methyl salicylate
• Diphenhydramine Hydrochloride
• Cetirizine dihydrochloride
• Bis[(4-chlorophenyl)methylene]carbonimidic dihydrazide hydrochloride
• Piperacillin
• METSULFURON METHYL
• Kresoxim-methyl
• Piperazine
• 1-AdaMantanethylaMine
• Thiophanate-methyl
• 2-Methylbenzotrifluoride
• Meclozine
• Tribenuron methyl
• 1-Methylpiperazine
• Promethazine hydrochloride
• Methyl acetate
• Chlorpromazine hydrochloride
• Chlorodimethylphenylsilane