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Mefloquine hydrochloride

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Name

Mefloquine hydrochloride

EINECS 257-412-0
CAS No. 51773-92-3 Density 1.383g/cm3
PSA 45.15000 LogP 5.57870
Solubility DMSO: 38 mg/mL Melting Point 250-254oC
Formula C17H16F6N2O.HCl Boiling Point 415.7oC at 760mmHg
Molecular Weight 414.778 Flash Point 205.2oC
Transport Information N/A Appearance white solid
Safety Risk Codes 22
Molecular Structure Molecular Structure of 51773-92-3 (Mefloquine hydrochloride) Hazard Symbols HarmfulXn
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;

Article Data 1

Mefloquine hydrochloride Specification

The IUPAC name of Mefloquine hydrochloride is [2,8-bis(trifluoromethyl)quinolin-4-yl]-piperidin-2-ylmethanol hydrochloride. With the CAS registry number 51773-92-3, it is also named as DL-erythro-alpha-2-Piperidyl-2,8-bis(trifluoromethyl)-4-quinolinemethanol monohydrochloride. The classification codes are Antimalarial; Drug / Therapeutic Agent; Human Data. The other registry number is 68682-28-0. It is white solid which is harmful if swallowed.

The other characteristics of this product can be summarized as: (1)H-Bond Donor: 3; (2)H-Bond Acceptor: 9; (3)Rotatable Bond Count: 2; (4)Exact Mass: 414.09336; (5)MonoIsotopic Mass: 414.09336; (6)Topological Polar Surface Area: 45.2; (7)Heavy Atom Count: 27; (8)Formal Charge: 0; (9)Complexity: 483; (10)Isotope Atom Count: 0; (11)Undefined Atom StereoCenter Count: 2; (12)Covalently-Bonded Unit: Count 2.

Preparation of Mefloquine hydrochloride: It can be obtained by (2,8-bis-trifluoromethyl-quinolin-4-yl)-pyridin-2-yl-methanone. This reaction needs reagents H2, HCl, catalytic agent PtO2 and solvent methanol, ethanol. The reaction time is 5.5 hours. The yield is 80%.

 

Uses of Mefloquine hydrochloride: It is a phospholipid-interacting antimalarial drug (antimalarials). And it is very effective against plasmodium falciparum with very few side effects.

People can use the following data to convert to the molecule structure. 
1. Smiles: c12c(c(cc(n2)C(F)(F)F)[C@@H]([C@H]2CCCCN2)O)cccc1C(F)(F)F.Cl
2. InChI: InChI=1/C17H16F6N2O.ClH/c18-16(19,20)11-5-3-4-9-10(15(26)12-6-1-2-7-24-12)8-13(17(21,22)23)25-14(9)11;/h3-5,8,12,15,24,26H,1-2,6-7H2;1H/t12-,15+;/m1./s1

The following are the toxicity data which has been tested.

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
man TDLo oral 11mg/kg/2W-I (11mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD Annals of Internal Medicine. Vol. 114, Pg. 994, 1991.
man TDLo oral 18mg/kg/5W-I (18mg/kg) PERIPHERAL NERVE AND SENSATION: PARESTHESIS

BEHAVIORAL: GENERAL ANESTHETIC
Annals of Internal Medicine. Vol. 117, Pg. 1058, 1992.
man TDLo oral 96mg/kg/52D-I (96mg/kg) BEHAVIORAL: "HALLUCINATIONS, DISTORTED PERCEPTIONS"

BEHAVIORAL: EXCITEMENT

BEHAVIORAL: AGGRESSION
Archives of Internal Medicine. Vol. 154, Pg. 2360, 1994.
 
rat LD50 intraperitoneal 130mg/kg (130mg/kg) GASTROINTESTINAL: NAUSEA OR VOMITING Acta Tropica. Vol. 37, Pg. 232, 1980.
rat LD50 oral 880mg/kg (880mg/kg) GASTROINTESTINAL: NAUSEA OR VOMITING Acta Tropica. Vol. 37, Pg. 232, 1980.
women TDLo oral 15mg/kg/3W-I (15mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

BEHAVIORAL: COMA
Medical Journal of Australia. Vol. 161, Pg. 453, 1994.
 

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