Cinnarizine

Base Information

• Chemical Name: Cinnarizine
• CAS No.: 298-57-7
• Molecular Formula: C26H28N2
• Molecular Weight: 368.522
• Hs Code.: 2933599090
• European Community (EC) Number: 240-749-2,206-064-8
• NSC Number: 290687
• UNII: 3DI2E1X18L
• DSSTox Substance ID: DTXSID80859311
• Nikkaji Number: J39.649D,J2.572K
• Wikipedia: Cinnarizine
• Wikidata: Q775073
• NCI Thesaurus Code: C76060
• Pharos Ligand ID: CRPTHNGFJ5DA
• Metabolomics Workbench ID: 42903
• ChEMBL ID: CHEMBL43064
• Mol file: 298-57-7.mol

Synonyms:1-(Diphenylmethyl)-4-(3-phenyl-2-propenyl)piperazine;Cinarizina Inkey;Cinarizina Ratiopharm;Cinarizine;Cinazière;Cinna;Cinnarizin AL;Cinnarizin Ratiopharm;Cinnarizin Siegfried;cinnarizin von ct;Cinnarizin-ratiopharm;Cinnarizine;Cinnarizine L Tartrate;Cinnarizine L-Tartrate;Cinnarizine L-Tartrate (1:1);Cinnarizine, (E)-Isomer;Cinnarizine, Dihydrochloride;Cinnipirine;Cisaken;Dihydrochloride Cinnarizine;Dimitronal;L-Tartrate, Cinnarizine;R 516;R-516;R516;Stugeron;Stugeron Forte;Von Ct, Cinnarizin

Chemical Property of Cinnarizine

Chemical Property:

• Appearance/Colour: white powder
• Vapor Pressure: 2.35E-10mmHg at 25°C
• Melting Point: 117-120oC
• Refractive Index: 1.649
• Boiling Point: 509.2oC at 760mmHg
• PKA: pKa 7.47(H2O t=25.0 ) (Uncertain)
• Flash Point: 229.8oC
• PSA: 6.48000
• Density: 1.093g/cm3
• LogP: 4.98280
• Storage Temp.: Refrigerator
• Solubility.: Soluble in chloroform at 50mg/ml
• Water Solubility.: 0.75g/L(temperature not stated)
• XLogP3: 5.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 6
• Exact Mass: 368.225248902
• Heavy Atom Count: 28
• Complexity: 429

Purity/Quality:

99% ^*data from raw suppliers

Cinnarizine >98.0%(HPLC)(N) ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 20/22-36/37/38-42/43
• Safety Statements: 22-24/25-36-26

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CN(CCN1CC=CC2=CC=CC=C2)C(C3=CC=CC=C3)C4=CC=CC=C4
• Isomeric SMILES: C1CN(CCN1C/C=C/C2=CC=CC=C2)C(C3=CC=CC=C3)C4=CC=CC=C4
• Recent ClinicalTrials: Effect of a Proposed Cav1.3 Inhibitor in Primary Aldosteronism
• Recent EU Clinical Trials: Efficacy and safety of a fixed combination of cinnarizine 20 mg and dimenhydrinate 40 mg vs betahistine dihydrochloride 16 mg in patients with vertigo of peripheral origin. A multi-centre, double-blind, randomised, active-controlled, stratified two-parallel group clinical study
• Uses: It is long-efficacy, multifunction vasoconstriction antagonists. It can dilate blood vessels, improve blood circulation and prevent blood vessel embrittlement. It can be used in the treatment of cerebral vascular diseases as well as has efficacy in treating cervical vertigo caused headaches, dizziness, insomnia, memory loss, paralysis, numbness, weakness and slurred speech embolism. glucocorticoid, antiinflammatory Histamine H1 receptor antagonist; antihistamine. For the treatment of vertigo/meniere's disease, nausea and vomiting, motion sickness and also useful for vestibular symptoms of other origins.
• Production method: It can be produced through: first use anhydrous piperazine and brominated diphenyl methane for preparation of benzhydryl piperazine, then condense with chlorine allyl benzene to obtain it. Diphenyl methane was heated in the light, add bromine and incubate for 1h at 130 ℃ which generates brominated diphenyl methane, C13H11Br, [776-74-9] with the melting point of 45 ℃. Add the brominated diphenyl methane drop wise into the piperazine toluene and stir for 3h at 80-90 ℃, further wash with water after cooling, then use 10% dilute hydrochloric acid for extraction; The acid layer was basified for being precipitated, filtered and dried to give benzhydryl piperazine. Dissolve it in 95% ethanol, add sodium carbonate and add drop wise of allyl benzene at about 65 ℃, after the completion of the dropping, heat and reflux for 4h, filter hot and the filtrate was left overnight for precipitate the crystalline, filter to get the crude product of Stugeron which under refinement become finished product with melting point of 117-119 ℃. In terms of diphenyl methane, the total yield is 48.2%.
• Therapeutic Function: Antihistaminic
• Clinical Use: Vestibular disorders Motion sickness
• Drug interactions: Potentially hazardous interactions with other drugs Analgesics: possibly increased sedative effects with opioid analgesics.

Technology Process of Cinnarizine

There total 30 articles about Cinnarizine 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: 95.0%

1-Phenyl-2-propen-1-ol (4393-06-0) + diphenylmethylpiperazine (841-77-0) → cinnarizine (298-57-7,16699-20-0)

Guidance literature:

With Pd(xantphos)(MeCN)₂(OTf)₂; In isopropyl alcohol; at 20 ℃; for 12h; Inert atmosphere;

DOI:10.1055/s-0034-1379249

Reference yield: 90.0%

3-Phenylpropenol (104-54-1) + diphenylmethylpiperazine (841-77-0) → cinnarizine (298-57-7,16699-20-0)

Guidance literature:

In o-xylene; at 150 ℃; for 30h; Inert atmosphere; Sealed tube;

DOI:10.1016/j.jcat.2019.12.012

Reference yield: 90.0%

1-[(2E)-3-chloroprop-2-en-1-yl]-4-(diphenylmethyl)piperazine + phenylmagnesium chloride (100-59-4) → cinnarizine (298-57-7,16699-20-0)

Guidance literature:

With 1-methyl-pyrrolidin-2-one; iron(III)-acetylacetonate; In tetrahydrofuran; at 0 - 20 ℃; Inert atmosphere;

DOI:10.1134/S1070428015010169

upstream raw materials:

3-Phenylpropenol

diphenylmethylpiperazine

3-phenyl-propenal

1-phenylpropadiene

Downstream raw materials:

cinnarizine hydrochloride

Refernces

• 1、 -. "Allyl coupling reaction method and application thereof". Paragraph 0304-0308. . Retrieved 2021/08/25.
• 2、 Wei, Jianwei,Zhao, Liang,He, Cheng,Zheng, Sijia,Reek, Joost N. H.,Duan, Chunying. "Metal-Organic Capsules with NADH Mimics as Switchable Selectivity Regulators for Photocatalytic Transfer Hydrogenation". . p. 12707 - 12716. Retrieved 2019/09/04.