31884-77-2

White Solid

Antiemetic

For the prevention and treatment of nausea, vomiting, or dizziness associated with motion sickness.

Antivert (Pfizer).

Antivert,Roerig,US,1957

ChEBI: Meclizine hydrochloride is a diarylmethane.

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.

Antinauseant

Meclizine hydrochloride,1-(p-chloro-α-phenylbenzyl)-4-(m-methylbenzyl)piperazinedihydrochloride monohydrate (Bonine, Antivert), is atasteless, white or slightly yellowish crystalline powder that is practically insoluble in water (1:1,000). It differs fromchlorcyclizine in having an N-m-methylbenzyl group inplace of the N-methyl group. Although it is a moderately potentantihistaminic, meclizine is used primarily as an antinauseantin the prevention and treatment of motion sicknessand in the treatment of nausea and vomiting associated withvertigo.