Mefloquine hydrochloride

Base Information

• Chemical Name: Mefloquine hydrochloride
• CAS No.: 51773-92-3
• Molecular Formula: C17H16F6N2O^.HCl
• Molecular Weight: 414.778
• Hs Code.: 2933399090
• European Community (EC) Number: 257-412-0
• Mol file: 51773-92-3.mol

Synonyms:4-Quinolinemethanol,a-(2R)-2-piperidinyl-2,8-bis(trifluoromethyl)-,monohydrochloride, (aS)-rel- (9CI);4-Quinolinemethanol, a-2-piperidinyl-2,8-bis(trifluoromethyl)-,monohydrochloride, (R*,S*)-(?à)-;4-Quinolinemethanol, a-2-piperidinyl-2,8-bis(trifluoromethyl)-, monohydrochloride, (R*,S*)-;Loriam;Mefloquin hydrochloride;NSC 157387;Ro21-5998/001;

Chemical Property of Mefloquine hydrochloride

Chemical Property:

• Appearance/Colour: white solid
• Vapor Pressure: 1.18E-07mmHg at 25°C
• Melting Point: 250-254oC
• Boiling Point: 415.7oC at 760mmHg
• Flash Point: 205.2oC
• PSA: 45.15000
• Density: 1.383g/cm3
• LogP: 5.57870
• Storage Temp.: Refrigerator
• Solubility.: DMSO: 38 mg/mL, soluble
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 9
• Rotatable Bond Count: 2
• Exact Mass: 414.0933598
• Heavy Atom Count: 27
• Complexity: 483

Purity/Quality:

98%99% ^*data from raw suppliers

Mefloquine Hydrochloride ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1CCNC(C1)C(C2=CC(=NC3=C2C=CC=C3C(F)(F)F)C(F)(F)F)O.Cl
• Isomeric SMILES: C1CCN[C@@H](C1)[C@H](C2=CC(=NC3=C2C=CC=C3C(F)(F)F)C(F)(F)F)O.Cl
• Description: Mefloquine hydrochloride is an erythrocytic schizonticide useful, in combination with sulfadoxine and pyrimethamine, in the prophylaxis and treatment of malaria. Administered once weekly, the combination is effective against pathogens resistant to other agents. Mefloquine is an orally bioavailable quinolinemethanol derivative with antimalarial properties. It increases mean survival time and abolishes malarial infection in mice at doses of 10 and 40 mg/kg, respectively. It inhibits hemozoin formation, leading to an increase in free heme in purified trophozoites. It acts as an antagonist at the adenosine A2A receptor, an agonist at serotonin 5-HT2A and 5-HT2C receptors, and has various effects on calcium homeostasis. Mefloquine increases the time mice spend in the light side of the light-dark box test and reduces immobility time in the tail suspension test, parameters typically associated with anxiolytic and antidepressant-like behavior. Formulations containing mefloquine have been used to prevent and treat malaria but have been associated with neuropsychiatric disturbances.
• Uses: Mefloquine Hydrochloride (Polymorph Form E) is a polymorphic form of Mefloquine Hydrochloride (M207055), a quinoline methanol antimalarial agent. Quinoline methanol antimalarial agent. Antimalarial;Heme polymerase inhibitor
• Clinical Use: The newest of the 4-aminoquinolines,mefloquine, is marketed as the R,S-isomer. It was developedin the 1960s as part of the U.S. Army’s WalterReed Institute for Medical Research antimalarial researchprogram. It differs significantly from the other agents in this class by having two trifluromethyl moieties at positions2’ and 8' and no electronegative substituents at eitherpositions 6' (quinine) or 7' (chloroquine). Mefloquine alsodiffers from chloroquine and its analogs by being a schizonticide acting before the parasite canenter the erythrocyte. There is some evidence that it acts byraising the pH in the parasite’s vesicles interfering with itsability to process heme. Mefloquine-resistant strains ofP. falciparum have appeared. Relapse can occur with acuteP. vivax that has been treated with mefloquine because thedrug does not eliminate the hepatic phase of this species,which can reinfect the liver.Mefloquine is teratogenic in rats, mice, and rabbits. Thereis an FDA-required warning that this drug can cause exacerbatemental disorders and is contraindicated in patients withactive depression, a recent history of depression, generalizedanxiety disorder, psychosis, schizophrenia, and other majorpsychiatric disorders or a history of convulsions.

Technology Process of Mefloquine hydrochloride

There total 6 articles about Mefloquine hydrochloride 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: 80.0%

[2,8-bis(trifluoromethyl)-4-quinolinyl]-2-pyridinylmethanone (35853-55-5) → mefloquine hydrochloride (51773-92-3,68682-28-0)

Guidance literature:

With hydrogenchloride; hydrogen; platinum(IV) oxide; In methanol; ethanol; for 5.5h;

DOI:10.1016/0040-4020(89)80138-3

Reference yield:

2,8-bis(trifluoromethyl)quinolin-4-ol (35853-41-9) → mefloquine hydrochloride (51773-92-3,68682-28-0)

Guidance literature:

Multi-step reaction with 4 steps

1: 90 percent / NaH / toluene; dimethylformamide / 20 h / 110 °C

2: 0.5 g / BuLi / tetrahydrofuran; hexane / Ambient temperature

3: 40 percent / TBAF / acetonitrile / 0.17 h / Ambient temperature

4: 80 percent / H₂, HCl / PtO₂ / methanol; ethanol / 5.5 h

With hydrogenchloride; n-butyllithium; tetrabutyl ammonium fluoride; hydrogen; sodium hydride; platinum(IV) oxide; In tetrahydrofuran; methanol; ethanol; hexane; N,N-dimethyl-formamide; toluene; acetonitrile;

DOI:10.1016/0040-4020(89)80138-3

Reference yield:

2-chloromethylpyridine hydrochloride (6959-47-3) → mefloquine hydrochloride (51773-92-3,68682-28-0)

Guidance literature:

Multi-step reaction with 4 steps

1: 90 percent / NaH / toluene; dimethylformamide / 20 h / 110 °C

2: 0.5 g / BuLi / tetrahydrofuran; hexane / Ambient temperature

3: 40 percent / TBAF / acetonitrile / 0.17 h / Ambient temperature

4: 80 percent / H₂, HCl / PtO₂ / methanol; ethanol / 5.5 h

With hydrogenchloride; n-butyllithium; tetrabutyl ammonium fluoride; hydrogen; sodium hydride; platinum(IV) oxide; In tetrahydrofuran; methanol; ethanol; hexane; N,N-dimethyl-formamide; toluene; acetonitrile;

DOI:10.1016/0040-4020(89)80138-3

upstream raw materials:

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

2,8-bis(trifluoromethyl)quinolin-4-ol

2-chloromethylpyridine hydrochloride

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

Downstream raw materials:

mefloquine

Refernces