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CAS 60-93-5

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(-)-Quinine dihydrochloride

Description:
(-)-Quinine dihydrochloride is a chemical compound derived from the bark of the cinchona tree, known for its historical use as an antimalarial agent. It is a stereoisomer of quinine, characterized by its specific optical activity, which is attributed to its chiral structure. The compound is a white to off-white crystalline powder that is soluble in water, making it suitable for various pharmaceutical applications. As a dihydrochloride salt, it contains two hydrochloride groups, enhancing its solubility and stability in aqueous solutions. (-)-Quinine dihydrochloride exhibits a bitter taste and has been used not only in medicine but also as a flavoring agent in tonic water. Its mechanism of action primarily involves the inhibition of heme polymerization in the malaria parasite, disrupting its ability to detoxify heme, which is toxic to the organism. Additionally, it has been studied for its potential effects on cardiac function and as an analgesic. Safety and dosage considerations are crucial, as it can have side effects and interactions with other medications.
Formula:C20H24N2O2·2ClH
InChI:InChI=1S/C20H24N2O2.2ClH/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;2*1H/t13-,14-,19-,20+;;/m0../s1
InChI key:InChIKey=NNKXWRRDHYTHFP-HZQSTTLBSA-N
SMILES:[C@@H](O)(C=1C2=C(C=CC(OC)=C2)N=CC1)[C@]3([N@@]4C[C@H](C=C)[C@](C3)(CC4)[H])[H].Cl
Synonyms:
  • (8alpha,9R)-6'-methoxycinchonan-9-ol dihydrochloride
  • Acid quinine hydrochloride
  • Cinchonan-9-ol, 6′-methoxy-, dihydrochloride, (8α,9R)-
  • Cinchonan-9-ol, 6′-methoxy-, hydrochloride (1:2), (8α,9R)-
  • Quinine Dihydochloride
  • Quinine bimuriate
  • Quinine, dihydrochloride
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