Dihydroquinine
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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 | |
Other names (8α,9R)-10,11-Dihydro-6'-methoxycinchonan-9-ol | |
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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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CompTox Dashboard (EPA) |
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InChI
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Properties | |
Chemical formula | 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). ![]() ![]() ![]() Infobox references |
Chemical compound
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]
See also
References
- ^ "Dihydroquinine chemical information". ChemIndustry.com.
- ^ Huffman, Aarin M.; Ayariga, Joseph A.; Napier, Audrey; Robertson, Boakai K.; Abugri, Daniel A. (2022). "Inhibition of Toxoplasma gondii Growth by Dihydroquinine and Its Mechanisms of Action". Frontiers in Cellular and Infection Microbiology. 12. doi:10.3389/fcimb.2022.852889. ISSN 2235-2988. PMC 9131874.
- v
- t
- e
Other drugs for disorders of the musculo-skeletal system (M09)
- Hydroquinine
- Bromelains
- Chymopapain
- Collagenase clostridium histolyticum
- Trypsin
- #WHO-EM
- ‡Withdrawn from market
- Clinical trials:
- †Phase III
- §Never to phase III