Cyclizine

Base Information

• Chemical Name: Cyclizine
• CAS No.: 82-92-8
• Molecular Formula: C18H22 N2
• Molecular Weight: 266.386
• Hs Code.: 2933599090
• European Community (EC) Number: 201-445-5
• NSC Number: 756710,26608
• UNII: QRW9FCR9P2
• DSSTox Substance ID: DTXSID4022864
• Nikkaji Number: J4.621C
• Wikipedia: Cyclizine
• Wikidata: Q867308
• NCI Thesaurus Code: C65356
• Pharos Ligand ID: 6DPLGY1Q8ZY5
• Metabolomics Workbench ID: 43393
• ChEMBL ID: CHEMBL648
• Mol file: 82-92-8.mol

Synonyms:Cyclizine;Cyclizine HCl;Cyclizine Hydrochloride;HCl, Cyclizine;Hydrochloride, Cyclizine;Marezine

Chemical Property of Cyclizine

Chemical Property:

• Melting Point: 105.5-107.5°
• Refractive Index: 1.5840 (estimate)
• Boiling Point: 399.58°C (rough estimate)
• PSA: 6.48000
• Density: 0.9934 (rough estimate)
• LogP: 2.89920
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility.: Slightly soluble in water and in ethanol (96 per cent).
• XLogP3: 3.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 3
• Exact Mass: 266.178298710
• Heavy Atom Count: 20
• Complexity: 253

Purity/Quality:

98% ^*data from raw suppliers

1-Benzhydryl-4-methylpiperazine 95% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CN1CCN(CC1)C(C2=CC=CC=C2)C3=CC=CC=C3
• Uses: Cyclizine exhibits antihistamine and anticholinergic action and is used for vomiting and diarrhea. The exact mechanism of action is not known. Synonyms of this drug are marezine and migril. Cyclizine is an antihistamine with a sedative effect used in the treatment of nausea and vomiting associated with motion sickness.

Technology Process of Cyclizine

There total 9 articles about Cyclizine 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: 96.19%

formaldehyd (50-00-0,30525-89-4,61233-19-0) + diphenylmethylpiperazine (841-77-0) → N-benzhydryl-N'-methylpiperazine (82-92-8)

Guidance literature:

formaldehyd; With formic acid; In water; at 20 ℃;

diphenylmethylpiperazine; In water; at 85 - 90 ℃; for 3h; Temperature;

Reference yield: 94.0%

1-methyl-piperazine (109-01-3) + diphenylchloromethane (90-99-3) → N-benzhydryl-N'-methylpiperazine (82-92-8)

Guidance literature:

In water; at 100 ℃; for 0.75h; Flow reactor;

DOI:10.1002/cssc.201501367

Reference yield: 72.0%

diphenylzinc (1078-58-6) + 1-[methoxy(phenyl)methyl]4-methylpiperazine → N-benzhydryl-N'-methylpiperazine (82-92-8)

Guidance literature:

With bis(pentafluorophenyl)zinc; In toluene; at 20 ℃; for 1h;

DOI:10.1039/d1cc04137a

upstream raw materials:

1-methyl-piperazine

diphenylchloromethane

1-benzhydryl-4-(ethoxycarbonyl)piperazine

N-Methyldiethanolamine

Downstream raw materials:

cyclizine hydrochloride

ethyl 2-(4-benzylhydrylpiperazin-1-yl)acetate

5-(4-benzhydryl-piperazin-1-yl)-pentanoic acid ethyl ester

6-(4-Benzhydryl-piperazin-1-yl)-hexanoic acid methyl ester

Refernces

• 1、 -. "AN IMPROVED PROCESS FOR THE PREPARATION OF AN ANTIHISTAMINE AGENT". Page/Page column 13-14. . Retrieved 2018/02/03.
• 2、 -. "SUBSTITUTED DIBENZHYDRYLPIPERAZINES". Page/Page column 26. . Retrieved 2009/07/18.