Meclozine Chemical Properties

Boiling point:

bp2 230°

Density 

1.0318 (rough estimate)

refractive index 

1.5940 (estimate)

storage temp. 

2-8°C

pka

pKa 2.05(H2O,t =25,I=0.0051(NaCl)) (Uncertain)

BCS Class

2

CAS DataBase Reference

569-65-3(CAS DataBase Reference)

NIST Chemistry Reference

Meclizine(569-65-3)

EPA Substance Registry System

Meclizine (569-65-3)

Safety Information

Hazardous Substances Data

569-65-3(Hazardous Substances Data)

MSDS

• Language:English Provider:Meclozine

Meclozine Usage And Synthesis

Originator

Antivert,Roerig,US,1957

Uses

Anti-emetic.

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.

Meclozine(569-65-3)Related Product Information

• Bensulfuron methyl
• Chlorodimethylphenylsilane
• 2-Chlorobenzaldehyde
• 2,4-Dichlorobenzyl chloride
• Thiophanate-methyl
• PHENYL VALERATE
• Methyl acrylate
• Triphenylmethyl Chloride
• Methylparaben
• Kresoxim-methyl
• Benzyl chloride
• 1-Methylpiperazine
• HEXACHLOROBENZENE
• tert-Butylchlorodiphenylsilane
• 1,3-Dichlorobenzene
• Chlorphenamine maleate
• 2-Methylbenzotrifluoride
• 4-Chlorotoluene