An antimalarial compound
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Mefloquine (hydrochloride)

Item No. 23665

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
rel-αS-(2R)-2-piperidinyl-2,8-bis(trifluoromethyl)-4-quinolinemethanol, monohydrochloride
CAS Number
51773-92-3
Synonyms
  • NSC 157387
  • Ro 21-5998/001
Molecular Formula
C17H16F6N2O • HCl
Formula Weight
414.8
Purity
≥98%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
DMF: 10 mg/mlDMSO: 20 mg/mlEthanol: 10 mg/ml
λmax
210, 222 nm
SMILES
O[C@H]([C@]1([H])NCCCC1)C2=CC(C(F)(F)F)=NC3=C(C(F)(F)F)C=CC=C32.Cl
InChi Code
InChI=1S/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
InChi Key
WESWYMRNZNDGBX-YLCXCWDSSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    Cayman Chemical
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    Product Description

    Mefloquine is an orally bioavailable quinolinemethanol derivative with antimalarial properties.1 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.2 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.3,4 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.4 Formulations containing mefloquine have been used to prevent and treat malaria but have been associated with neuropsychiatric disturbances.

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Ohnmacht, C.J., Patel, A.R., and Lutz, R.E. Antimalarials. 7. Bis(trifluoromethyl)-α-(2-piperidyl)-4-quinolinemethanols. J. Med. Chem. 14(10), 926-928 (1971).

    2. Combrinck, J.M., Mabotha, T.E., Ncokazi, K.K., et al. Insights into the role of heme in the mechanism of action of antimalarials. ACS Chem Biol. 8(1), 133-137 (2013).

    3. Grabias, B., and Kumar, S. Adverse neuropsychiatric effects of antimalarial drugs. Expert Opin. Drug Saf. 15(7), 903-910 (2016).

    4. Holden, J.M., Slivicki, R., Dahl, R., et al. Behavioral effects of mefloquine in tail suspension and light/dark tests. Springerplus 4:702, (2015).