quinine, CAS No. 6119-70-6

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6119-70-6

Catalog No. EBD30211

CAS 6119-70-6

Name quinine

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Basic Information

Synonyms: Quininesulfatedihydrate quininesulfateusp quininehemisulfate Quininesulphatedihydrate Quininesulfatesaltdihydrate (8alpha,9R)-6'-methoxycinchonan-9-olsulfatehydrate(2:1:2) Sulfat-Octahydrat quinine

Molecular Formula: C20H28N2O7S

Molecular Weight: 440.51

MDL Number: MFCD00150790

Categories: Medicinal Chemistry > Pharmaceutical Excipients > Pharmaceutical Sweeteners

Product Description:

Quinine hemisulfate monohydrate is a salt form of the naturally occurring alkaloid quinine, derived from the bark of the *Cinchona* tree. It is a white or almost white, crystalline powder. The compound is a stereoisomer of quinidine and contains a quinoline moiety fused to a quinuclidine system. Its primary and most significant application is as an antimalarial drug. It is used for the treatment of severe and complicated malaria caused by *Plasmodium falciparum*, particularly in cases of chloroquine resistance. Its mechanism of action involves the inhibition of hemozoin biocrystallization within the parasite, leading to toxic accumulation of free heme. Beyond its antimalarial use, it has historically been used as a bitter flavoring agent in tonic water and beverages. Due to its complex, chiral, and nitrogen-rich heterocyclic structure, quinine and its salts, including the hemisulfate, serve as important chiral building blocks and catalysts in organic synthesis. They are frequently employed as chiral bases, ligands, or phase-transfer catalysts in asymmetric synthesis.

Physical Properties

Melting Point: ~225 °C (dec.)(lit.)

Boiling Point: 992.5 °C at 760 mmHg

Flash Point: 554 °C

Solubility: 0.12 g/100 mL (20 ºC)

Analytical Data

Appearance: white crystalline powder