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145912 Sigma-Aldrich

Quinine hemisulfate salt monohydrate

90%

Synonym: Quinine sulfate (2:1) (salt) dihydrate

  • CAS Number 207671-44-1

  • Empirical Formula (Hill Notation) C20H24N2O2 · 0.5H2O4S · H2O

  • Molecular Weight 391.47

  •  Beilstein/REAXYS Number 6113937

  •  MDL number MFCD00150790

  •  PubChem Substance ID 329750544

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Properties

Related Categories Alkaloid, Antibiotics, Antibiotics A to Z, Antibiotics N-S, Antiparasitic / Antiprotozoal / Anthelminthic,
assay   90%
optical activity   [α]25/D −229°, c = 2 in 0.1 M HCl
mp   ~225 °C (dec.) (lit.)
  233-235 °C (dec.)
Mode of action   enzyme | inhibits
antibiotic activity spectrum   parasites
SMILES string   O.O.OS(O)(=O)=O.COc1ccc2nccc([C@@H](O)C3CC4CCN3C[C@@H]4C=C)c2c1.COc5ccc6nccc([C@@H](O)C7CC8CCN7C[C@@H]8C=C)c6c5
InChI   1S/2C20H24N2O2.H2O4S.2H2O/c2*1-3-13-12-22-9-7-14(13)10-19(22)20(23)16-6-8-21-18-5-4-15(24-2)11-17(16)18;1-5(2,3)4;;/h2*3-6,8,11,13-14,19-20,23H,1,7,9-10,12H2,2H3;(H2,1,2,3,4);2*1H2/t2*13-,14-,19-,20+;;;/m00.../s1
InChI key   ZHNFLHYOFXQIOW-LPYZJUEESA-N

Description

Biochem/physiol Actions

Potassium channel blocker. Antimalarial, anticholinergic, antihypertensive, and hypoglycemic agent; alkaloid originally isolated from the Cinchona family of South American trees. Inhibits mitochondrial ATP-regulated potassium channel. Used to study the metabolism of biocrystalized heme, hemozoin, in malarial parasites and to study the toxicity of heme (FP)-complexes.

Other Notes

Contains hydroquinine sulfate monohydrate

Safety & Documentation

Safety Information

Symbol 
GHS07  GHS07
Signal word 
Warning
Hazard statements 
Precautionary statements 
Personal Protective Equipment 
RIDADR 
NONH for all modes of transport
WGK Germany 
3
Protocols & Articles

Articles

Cinchona Alkaloids - Aldrich ChemFiles 2008, 8.2, 74.

Cinchona alkaloids and their derivatives have proven to catalyze an astonishing array of enantioselective transformations, providing access to chiral products of high enantiopurity.1 The presence of ...
William Sommer and Daniel Weibel
Aldrich ChemFiles 2008, 8.2, 74.
Keywords: Addition reactions, Aminations, Antimicrobials, Asymmetric synthesis, Catalysis, Desymmetrizations, Dihydroxylations, Ligands, Reductive aminations

Peer-Reviewed Papers
15

References

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Q1250 Quinine hemisulfate salt monohydrate, synthetic, ≥90% (HPLC)

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