Names | |
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IUPAC name
(R)-[(2S,4S,5R)-5-ethyl-1-azabicyclo[2.2.2]octan-2-yl]-(6-methoxyquinolin-4-yl)methanol
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Other names
(8α,9R)-10,11-Dihydro-6'-methoxycinchonan-9-ol
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Identifiers | |
CAS Number
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3D model (JSmol)
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ChemSpider |
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ECHA InfoCard | 100.007.578 |
PubChem CID
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UNII |
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CompTox Dashboard (EPA)
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InChI
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SMILES
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Properties | |
Chemical formula
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C20H26N2O2 |
Molar mass | 326.440 g·mol−1 |
Melting point | 173–175 °C |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references
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Dihydroquinine, also known as hydroquinine[1] or DHQ, is an organic compound and as a cinchona alkaloid closely related to quinine. The specific rotation is −148° in ethanol. A derivative of this molecule is used as chiral ligand in the AD-mix for Sharpless dihydroxylation.
DHQ also inhibits growth of the parasite Toxoplasma gondii by inducing mitochondrial membrane damage, but does not disrupt host mitochondrial membrane potential, as well as reactive oxygen species (ROS) generation.[2]