Mefloquine

Base Information

• Chemical Name: Mefloquine
• CAS No.: 49752-90-1
• Molecular Formula: C17H16F6N2O
• Molecular Weight: 378.317
• European Community (EC) Number: 256-468-3
• DSSTox Substance ID: DTXSID50860636
• Nikkaji Number: J320.015I
• Wikipedia: Mefloquine
• Wikidata: Q736270
• NCI Thesaurus Code: C61827
• RXCUI: 6694
• Pharos Ligand ID: HLVV3DA4ZATG
• Metabolomics Workbench ID: 145102
• ChEMBL ID: CHEMBL416956
• Mol file: 49752-90-1.mol

Synonyms:Lariam;Mefloquine;Mefloquine Hydrochloride;Mephloquine;Ro 21 5998 001;Ro-21-5998-001;Ro215998001;WR 142,490;WR 177,602;WR-142,490;WR-177,602;WR142,490;WR177,602

Chemical Property of Mefloquine

Chemical Property:

• Boiling Point: 415.7°Cat760mmHg
• Flash Point: 205.2°C
• PSA: 45.15000
• Density: 1.383g/cm³
• LogP: 4.77670
• XLogP3: 3.6
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 9
• Rotatable Bond Count: 2
• Exact Mass: 378.11668211
• Heavy Atom Count: 26
• Complexity: 483

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Drug Classes: Antimalarial Agents
• Canonical SMILES: C1CCNC(C1)C(C2=CC(=NC3=C2C=CC=C3C(F)(F)F)C(F)(F)F)O
• Recent ClinicalTrials: Temozolomide, Memantine Hydrochloride, Mefloquine, and Metformin Hydrochloride in Treating Patients With Glioblastoma Multiforme After Radiation Therapy
• Recent EU Clinical Trials: Pilot study to evaluate the efficacy and safety of mefloquine as prophylaxis in people exposed to the disease caused by the SARS-CoV-2 coronavirus (COVID-19)
• Recent NIPH Clinical Trials: The efficacy and safety of mefloquine in patients with progressive multifocal leukoencephalopathy

Technology Process of Mefloquine

There total 32 articles about Mefloquine 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: 93.0%

C17H14F6N2O*2C12H10O3S → mefloquine (49752-90-1,51688-68-7,51742-87-1,53230-10-7,58737-31-8,68682-27-9,147368-41-0,148690-80-6)

Guidance literature:

With sodium tetrahydroborate; cerium(III) chloride heptahydrate; In ethanol; at 0 ℃; for 5h;

DOI:10.1002/anie.201811289

Reference yield: 91.0%

2-(4-((2S,3S)-3-(2,8-bis(trifluoromethyl)quinolin-4-yl)oxiran-2-yl)butyl)isoindoline-1,3-dione → mefloquine (49752-90-1,51688-68-7,51742-87-1,53230-10-7,58737-31-8,68682-27-9,147368-41-0,148690-80-6)

Guidance literature:

With ethanol; hydrazine hydrate; for 2h; Reflux;

DOI:10.1002/anie.201507304

Reference yield: 89.0%

(+)-(11S,12R)-erythro-mefloquine, O,O-(-)-di-p-toluoyl-L-tartrate (705291-21-0) → mefloquine (49752-90-1,51688-68-7,51742-87-1,53230-10-7,58737-31-8,68682-27-9,147368-41-0,148690-80-6)

Guidance literature:

With sodium hydroxide; In methanol; water; at 20 ℃; for 3.5h; pH=14;

upstream raw materials:

(2,8-bis-trifluoromethyl)-4-bromoquinoline

2,8-bis-(trifluoromethyl)-quinoline-4-carboxylic acid

[2,8-bis(trifluoromethyl)-4-quinolinyl]-2-pyridinylmethanone

2,4-dimethyl-3-(pyridin-2-ylmethyl)pentan-3-ol

Downstream raw materials:

4-hydroxymethyl-2,8-bis(trifluoromethyl)quinoline

(2,8-bis-trifluoromethyl-quinolin-4-yl)-piperidin-2-yl-methanol; hydrochloride

(R)-2-((S)-(2,8-bis(trifluoromethyl)quinolin-4-yl)(hydroxy)methyl)piperidin-1-ium chloride

(R)-tert-butyl 2-((S)-(2,8-bis(trifluoromethyl)quinolin-4-yl)(hydroxy)methyl)piperidine-1-carboxylate

Refernces

• 1、 Boratyński, Przemys?aw J.,Kowalczyk, Rafa?,Kucharski, Dawid J.. "Chiral Vicinal Diamines Derived from Mefloquine". . p. 10654 - 10664. Retrieved 2021/08/20.
• 2、 Kreituss, Imants,Chen, Kuang-Yen,Eitel, Simon H.,Adam, Jean-Michel,Wuitschik, Georg,Fettes, Alec,Bode, Jeffrey W.. "A Robust, Recyclable Resin for Decagram Scale Resolution of (±)-Mefloquine and Other Chiral N-Heterocycles". supporting information. p. 1553 - 1556. Retrieved 2016/02/12.