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Merck

359343

Hydroquinidine

95%

Synonym(s):

(9S)-10,11-Dihydro-6′-methoxycinchonan-9-ol, Dihydroquinidine

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About This Item

Empirical Formula (Hill Notation):
C20H26N2O2
CAS Number:
1435-55-8
Molecular Weight:
326.43
UNSPSC Code:
12352005
NACRES:
NA.22
PubChem Substance ID:
24862070
EC Number:
215-862-5
Beilstein/REAXYS Number:
91441
MDL number:
MFCD00135599

Key Documents

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InChI key

LJOQGZACKSYWCH-LHHVKLHASA-N

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

SMILES string

CC[C@H]1CN2CCC1CC2[C@@H](O)c3ccnc4ccc(OC)cc34

assay

95%

optical activity

[α]25/D +226°, c = 2 in ethanol

mp

169-170 °C (lit.)

functional group

hydroxyl

Quality Level

100

Gene Information

human ... CYP2D6(1565)

Related Categories

General description

Hydroquinidine, a cinchona alkaloid, is a structural analog of quinidine. It shows antiarrhythmic effect.

Application

Hydroquinidine can be used as a chiral catalyst to prepare:
  • Enantioselective axially chiral phosphamides by N-allylic alkylation reaction between Morita-Baylis-Hillamn (MBH) carbonate and phosphamides.
  • Enantioselective α-amino phosphonates by hydrophosphonylation of N-aryl ketimines.
  • Enantioselective α-hydrazino esters by α-hydrazination of 3-oxoindolines using azodicarboxylate via aza-Michael reaction.

pictograms

Exclamation mark
GHS07

signalword

Warning

hcodes

H302

Hazard Classifications

Acute Tox. 4 Oral

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
MKCR4533
MKCJ6223
MKBR2658V
MKBJ3519V
MKBG3366V

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Comparison of serum hydroquinidine determination by fluorescence polarization immunoassay and liquid chromatography.
Tod M, et al.
Journal of Pharmaceutical and Biomedical Analysis, 8(3), 279-282 (1990)
Asymmetric Synthesis of Axially Chiral Phosphamides via Atroposelective N-Allylic Alkylation
Yang GH et al.
ACS Catalysis, 10, 2324-2333 (2020)
Organocatalytic enantioselective amination of 2-substituted indolin-3-ones: A strategy for the synthesis of chiral $\alpha$-hydrazino esters
Yarlagadda S, et al.
Organic Letters, 19, 170-173 (2017)
Relationships between heart rate variability and antiarrhythmic effects of hydroquinidine.
Brembilla-Perrot B and Jacquemin L
Cardiovascular Drugs and Therapy, 11(3), 493-498 (1997)
Catalytic enantioselective hydrophosphonylation of ketimines using cinchona alkaloids.
Nakamura S, et al.
Journal of the American Chemical Society, 131(51), 18240-18241 (2009)
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