Meclozine

Meclozine Basic information
Product Name:Meclozine
Synonyms:UCB 5052;UCB 5062;Vomisseis;Vomissels;1-(p-Chloro-a-phenylbenzyl)-4-(m-methylbenzyl)piperazine;mecilizine;NSC 169189;Piperazine, 1-(p-chloro-a-phenylbenzyl)-4-(m-methylbenzyl)- (6CI, 8CI)
CAS:569-65-3
MF:C25H27ClN2
MW:390.95
EINECS:209-323-3
Product Categories:
Mol File:569-65-3.mol
Meclozine Structure
Meclozine Chemical Properties
Boiling point bp2 230°
density 1.0318 (rough estimate)
refractive index 1.5940 (estimate)
storage temp. 2-8°C
pkapKa 2.05(H2O,t =25,I=0.0051(NaCl)) (Uncertain)
BCS Class2
CAS DataBase Reference569-65-3(CAS DataBase Reference)
NIST Chemistry ReferenceMeclizine(569-65-3)
EPA Substance Registry SystemMeclizine (569-65-3)
Safety Information
Hazardous Substances Data569-65-3(Hazardous Substances Data)
MSDS Information
ProviderLanguage
Meclozine English
Meclozine Usage And Synthesis
OriginatorAntivert,Roerig,US,1957
UsesAnti-emetic.
UsesMeclizine actively affects the vomiting center and is used for vomiting and diarrhea. Synonyms of this drug are antivert, bonine, lamin, roclizin, and vertol.
DefinitionChEBI: Meclizine is a diarylmethane.
Manufacturing Process32.3 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 nameAntivert (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 FunctionAntinauseant
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.
SynthesisMeclizine, 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.

Synthesis_569-65-3

Meclozine Preparation Products And Raw materials
Raw materialsBenzyl chloride-->Sodium amide-->CHLORCYCLIZINE-->1-Benzylpiperazine-->1-BENZHYDRYLPIPERAZINE-->Hydrogen-->3-Methylbenzyl chloride
Methylparaben Chlorodimethylphenylsilane Benzyl chloride Bensulfuron methyl Parathion-methyl HEXACHLOROBENZENE 1-Methylpiperazine Kresoxim-methyl PHENYL VALERATE IMP. A (EP): CHLORPHENAMINE (USP: CHLORPHENIRAMINE) p-Dichlorobenzene Thiophanate-methyl Triphenylmethyl Chloride Methyl acrylate tert-Butylchlorodiphenylsilane Meclozine dihydrochloride monohydrate,mecilizine hydrochloride 2,4-Dichlorobenzyl chloride 2-Chlorobenzaldehyde

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