Chemical Properties
Boiling point: 230°C (0.267 kPa). Its hydrochloride ([1104-22-9]) has a melting point of 224°C (decomposition). It is soluble in chloroform and pyridine, but insoluble in water and ether.
Originator
Antivert,Roerig,US,1957
Uses
Meclizine actively affects the vomiting center and is used for vomiting and diarrhea.
Synonyms of this drug are antivert, bonine, lamin, roclizin, and vertol.
Definition
ChEBI: Meclizine is a diarylmethane.
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);Ancoloxine;Bonamina;Bonamine;Calmonal;Chiclida;Cobinamide;Diadril;Dradril;Duremesan;Itinerol;Mecazine;Navicalm;Neo-istafenc;Neo-istafene;Peremesin;Postafene;Premesin;Rovert-m;Ru-vert-m;Sea-leg;Supermesin;Superminal;Suprimal;Taizerl;V-cline;Veritab;Vertizine;Vomaxine;Vomisseis.
Therapeutic Function
Antinauseant
World Health Organization (WHO)
Meclozine, an antihistamine with antiemetic activity, was
introduced in 1953 for the treatment of nausea. The action taken in Indonesia in
1963 resulted from concern regarding its possible teratogenic potential.
Subsequent epidemiological studies have been widely accepted, however, as
dispelling this suspicion. Meclozine remains widely available in both prescription
only and over-the-counter preparations and in some countries the licensed
indications include management of nausea of pregnancy.
Synthesis
Meclizine, 1-[(4-chlorphenyl)methyl]-4-[(3-methylphenyl)phenyl]piperazine
(16.1.16), is synthesized by reductive amination of a mixture of 3-methylbenzaldehyde
with 1-(4-chlorbenzhydryl)piperazine using hydrogen over Raney nickel.
