An antimalarial agent
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Isomer(s)
20356Quinidine
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Quinine

Item No. 23958

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(8α,9R)-6'-methoxy-cinchonan-9-ol
CAS Number
130-95-0
Synonyms
  • NSC 192949
Molecular Formula
C20H24N2O2
Formula Weight
324.4
Purity
≥95%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 30 mg/mlDMSO: 30 mg/mlEthanol: 30 mg/ml
λmax
230, 278, 331 nm
SMILES
COC1=CC=C2C(C([C@@H](O)[C@]3([H])C[C@H]4[C@@H](C=C)C[N@@]3CC4)=CC=N2)=C1
InChi Code
InChI=1S/C20H24N2O2/c1-3-13-12-22-9-7-14(13)10-19(22)20(23)16-6-8-21-18-5-4-15(24-2)11-17(16)18/h3-6,8,11,13-14,19-20,23H,1,7,9-10,12H2,2H3/t13-,14-,19-,20+/m0/s1
InChi Key
LOUPRKONTZGTKE-WZBLMQSHSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    1 g

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    Cayman Chemical
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    Product Description

    Quinine is an alkaloid antimalarial agent that has MIC values ranging from 10 to 500 nM for 60 Thai isolates of P. falciparum.1 It inhibits hemozoin formation in purified trophozoites, leading to an increase in free heme, similar to the mechanism of action of chloroquine (Item No. 14194).2 In mice, quinine reduces P. berghei parasite load in the blood with a minimum effective dose (MED) of 150 mg/kg.3 Formulations containing quinine have been used in the treatment of uncomplicated malaria.

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Thaithong, S., Beale, G.H., and Chutmongkonkul, M. Susceptibility of Plasmodium falciparum to five drugs: An in vitro study of isolates mainly from Thailand. Trans. R. Soc. Trop. Med. Hyg. 77(2), 228-231 (1983).

    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. Thurston, J.P. The action of antimalarial drugs in mice infected with Plasmodium berghei. Br. J. Pharmacol. Chemother. 5(3), 409-416 (1950).