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Dihydroquinidine information


Dihydroquinidine
Names
IUPAC name
(S)-[(2R,4S,5R)-5-ethyl-1-azabicyclo[2.2.2]octan-2-yl]-(6-methoxyquinolin-4-yl)methanol
Other names
(9S)-10,11-Dihydro-6'-methoxycinchonan-9-ol
Identifiers
CAS Number
  • 1435-55-8 checkY
3D model (JSmol)
  • Interactive image
ChEMBL
  • ChEMBL280522 ☒N
ChemSpider
  • 82624
ECHA InfoCard 100.007.578 Edit this at Wikidata
PubChem CID
  • 91503
UNII
  • 8P68XPY4HG ☒N
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-LHHVKLHASA-N
SMILES
  • [C@H](O)(C=1C2=C(C=CC(OC)=C2)N=CC1)[C@@]3([N@@]4C[C@H](CC)[C@H](C3)CC4)[H]
Properties
Chemical formula
 C20H26N2O2
Molar mass 326.440 g·mol−1
Melting point 169 to 172 °C (336 to 342 °F; 442 to 445 K)
Pharmacology
ATC code
 C01BA13 (WHO)
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

Dihydroquinidine (also called hydroquinidine) is an organic compound, a cinchona alkaloid closely related to quinine. The specific rotation is +226° in ethanol at 2 g/100 ml. A derivative of this molecule is used as chiral ligand in the AD-mix for Sharpless dihydroxylation.

The substance is also a class Ia antiarrhythmic medication.[1]

  1. ^ Drugs.com: International Drug Names for hydroquinidine.

and 8 Related for: Dihydroquinidine information

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Dihydroquinidine

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Dihydroquinidine (also called hydroquinidine) is an organic compound, a cinchona alkaloid closely related to quinine. The specific rotation is +226° in...

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Sharpless asymmetric dihydroxylation

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are realized, with the chiral outcome controlled by the choice of dihydroquinidine (DHQD) vs dihydroquinine (DHQ) as the ligand. Asymmetric dihydroxylation...

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Dihydroquinine

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membrane potential, as well as reactive oxygen species (ROS) generation. Dihydroquinidine "Dihydroquinine chemical information". ChemIndustry.com. Huffman, Aarin...

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C20H26N2O2

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formula C20H26N2O2 (molar mass: 326.4 g/mol) may refer to: Ajmaline Dihydroquinidine Dihydroquinine Epsiprantel Tortuosamine Vincaminol This set index page...

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Cinchona

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quinidine (stereoisomers with R1 = vinyl, R2 = methoxy) dihydroquinine and dihydroquinidine (stereoisomers with R1 = ethyl, R2 = methoxy) They find use in organic...

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Ofloxacin

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and arrhythmias is increased when co-administered with drugs such as dihydroquinidine barbiturate, quinidine, and quinidine barbiturate. Current or past...

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DHQD

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DHQD may refer to: Dihydroquinidine, a chemical compound 3-dehydroquinate dehydratase, an enzyme This disambiguation page lists articles associated with...

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Dihydroxylation

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performed in the presence of a chiral auxiliary. The selection of dihydroquinidine (DHQD) or dihydroquinine (DHQ) as a chiral auxiliary dictates the facial...

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