Dihydroquinine

Dihydroquinine
Names
	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
Identifiers
CAS Number	522-66-7 ;
3D model (JSmol)	Interactive image; Interactive image;
ChemSpider	108426 ;
ECHA InfoCard	100.007.578
PubChem CID	121515;
UNII	31J3Q51T6L ;
CompTox Dashboard (EPA)	DTXSID70878516 ;
	InChI InChI=1S/C20H26N2O2/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/h4-6,8,11,13-14,19-20,23H,3,7,9-10,12H2,1-2H3/t13-,14-,19-,20+/m0/s1 Key: LJOQGZACKSYWCH-WZBLMQSHSA-N ; InChI=1/C20H26N2O2/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/h4-6,8,11,13-14,19-20,23H,3,7,9-10,12H2,1-2H3/t13-,14-,19-,20+/m0/s1 Key: LJOQGZACKSYWCH-WZBLMQSHBC;
	SMILES O[C@@H](C1N2CCC(C(CC)C2)C1)C3=CC=NC4=CC=C(OC)C=C43; O(c4cc1c(nccc1[C@@H](O)[C@H]2N3CC[C@@H](C2)[C@@H](CC)C3)cc4)C;
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). verify (what is ?) Infobox references

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]

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.