Meclizine

Base Information

• Chemical Name: Meclizine
• CAS No.: 569-65-3
• Deprecated CAS: 1286986-99-9
• Molecular Formula: C25H27ClN2
• Molecular Weight: 390.956
• Hs Code.: 2933599090
• European Community (EC) Number: 209-323-3
• NSC Number: 169189
• UNII: 3L5TQ84570
• DSSTox Substance ID: DTXSID0023242
• Nikkaji Number: J6.532C
• Wikipedia: Meclizine
• Wikidata: Q386441
• NCI Thesaurus Code: C61610
• RXCUI: 6676
• Pharos Ligand ID: RBDRY4WX94Y1
• Metabolomics Workbench ID: 43041
• ChEMBL ID: CHEMBL1623
• Mol file: 569-65-3.mol

Synonyms:Agyrax;Antivert;Bonamine;Bonine;Chiclida;D Vert;D-Vert;Dihydrochloride, Meclizine;DVert;Histametizyn;Hydrochloride, Meclizine;Meclizine;Meclizine Dihydrochloride;Meclizine Hydrochloride;Meclizine Monohydrochloride;Meclozine;Monohydrochloride, Meclizine;Parachloramine;Ru Vert M;Ru-Vert-M

Chemical Property of Meclizine

Chemical Property:

• Melting Point: 153-157oC
• Refractive Index: 1.5940 (estimate)
• Boiling Point: 495.3 °C at 760 mmHg
• PKA: pKa 2.05(H2O,t =25,I=0.0051(NaCl)) (Uncertain)
• Flash Point: 253.3 °C
• PSA: 6.48000
• Density: 1.159 g/cm³
• LogP: 6.23340
• Storage Temp.: 2-8°C
• XLogP3: 5.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 5
• Exact Mass: 390.1862766
• Heavy Atom Count: 28
• Complexity: 448

Purity/Quality:

99% ^*data from raw suppliers

Meclizine 95 ^*data from reagent suppliers

Safty Information:

• Pictogram(s): R22;R36/37/38:
• Hazard Codes: Xn:
• Statements: R22;R36/37/38:
• Safety Statements: S26;S37/39:

MSDS Files:

SDS file from LookChem

Useful:

• Drug Classes: Antihistamines
• Canonical SMILES: CC1=CC(=CC=C1)CN2CCN(CC2)C(C3=CC=CC=C3)C4=CC=C(C=C4)Cl
• Recent ClinicalTrials: Meclizine for Hepatocellular Carcinoma
• Uses: Anti-emetic. Meclizine actively affects the vomiting center and is used for vomiting and diarrhea. Synonyms of this drug are antivert, bonine, lamin, roclizin, and vertol.
• Therapeutic Function: Antinauseant

Technology Process of Meclizine

There total 8 articles about Meclizine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 96.0%

N-(4-chlorobenzhydryl)piperazine (303-26-4) + sodium hydroxy(m-tolyl)methanesulfonate → meclizine (569-65-3,163837-49-8,163837-50-1,189298-48-4,189298-47-3)

Guidance literature:

With 2-picoline borane complex; In methanol; water; at 60 ℃; for 6h; Sealed tube; Inert atmosphere;

DOI:10.1021/acs.orglett.1c02604

Reference yield: 87.0%

N-(4-chlorobenzhydryl)piperazine (303-26-4) + 4-nitrophenyl bis(carbomethoxy) 3-(3-methylbenzyl)ylide → meclizine (569-65-3,163837-49-8,163837-50-1,189298-48-4,189298-47-3)

Guidance literature:

With trifluorormethanesulfonic acid; In dichloromethane; at 20 ℃; for 24h; Molecular sieve;

DOI:10.1016/j.cclet.2021.06.069

Reference yield: 87.0%

N-(4-chlorobenzhydryl)piperazine (303-26-4) + m-tolyl aldehyde (620-23-5) → meclizine (569-65-3,163837-49-8,163837-50-1,189298-48-4,189298-47-3)

Guidance literature:

With formic acid; boron trifluoride diethyl etherate; In acetonitrile; at 85 ℃; for 5h; Green chemistry;

DOI:10.1039/d1gc01468d

upstream raw materials:

1-(3-methylbenzyl)piperazine

4-chlorobenzaldehyde

N-(4-chlorobenzhydryl)piperazine

m-tolyl aldehyde

Downstream raw materials:

4-chlorophenyl(phenyl)methane

Refernces

• 1、 Cai, Lei,Chen, Qi,Fang, Jing,Li, Ting,Liao, Zhiwen,Ma, Xiang,Meng, Lingkui,Sun, Jiuchang,Wan, Qian,Zeng, Jing. "Discriminating non-ylidic carbon-sulfur bond cleavages of sulfonium ylides for alkylation and arylation reactions". supporting information. . Retrieved 2021/07/25.
• 2、 Ouyang, Lu,Xia, Yanping,Liao, Jianhua,Luo, Renshi. "One-Pot Transfer Hydrogenation Reductive Amination of Aldehydes and Ketones by Iridium Complexes “on Water”". . p. 6387 - 6391. Retrieved 2020/09/11.