Introduction：Basic information about Meclozine CAS 569-65-3, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.
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 |
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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
| TSCA | TSCA listed |
| Hazardous Substances Data | 569-65-3(Hazardous Substances Data) |
Meclozine Usage And Synthesis
| 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 | 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. Thissolution is washed with a saturated solution of K2CO3 and dried on K2CO3. Thesolvent is evaporated and the residue is distilled under high vacuum. Theproduct of the condensation distills near 230°C at 2 mm Hg pressure and thecorresponding 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, wasintroduced in 1953 for the treatment of nausea. The action taken in Indonesia in1963 resulted from concern regarding its possible teratogenic potential.Subsequent epidemiological studies have been widely accepted, however, asdispelling this suspicion. Meclozine remains widely available in both prescriptiononly and over-the-counter preparations and in some countries the licensedindications 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-methylbenzaldehydewith 1-(4-chlorbenzhydryl)piperazine using hydrogen over Raney nickel. |
Meclozine Preparation Products And Raw materials
| Raw materials | Benzyl chloride-->Sodium amide-->CHLORCYCLIZINE-->1-Benzylpiperazine-->1-BENZHYDRYLPIPERAZINE-->Hydrogen-->3-Methylbenzyl chloride |
