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Merck

27370

Cinchonine

crystallized, ≥98.0% (NT)

Synonym(s):

NSC 6176

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About This Item

Empirical Formula (Hill Notation):
C19H22N2O
CAS Number:
118-10-5
Molecular Weight:
294.39
UNSPSC Code:
12352104
NACRES:
NA.22
PubChem Substance ID:
57648242
EC Number:
204-234-6
Beilstein/REAXYS Number:
89689
MDL number:
MFCD00064372

Key Documents

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InChI key

KMPWYEUPVWOPIM-QAMTZSDWSA-N

InChI

1S/C19H22N2O/c1-2-13-12-21-10-8-14(13)11-18(21)19(22)16-7-9-20-17-6-4-3-5-15(16)17/h2-7,9,13-14,18-19,22H,1,8,10-12H2/t13-,14-,18+,19-/m0/s1

SMILES string

O[C@H]([C@H]1C[C@@H]2CCN1C[C@@H]2C=C)c3ccnc4ccccc34

assay

≥98.0% (NT)

form

powder

optical activity

[α]20/D +225±5°, c = 0.5% in ethanol

quality

crystallized

impurities

~15% dihydrocinchonine (HPLC)

mp

260-263 °C

functional group

hydroxyl

Quality Level

100

Gene Information

human ... CYP2D6(1565)

Related Categories

General description

Cinchonine is a cinchona alkaloid generally found in the bark of Cinchona officinalis plants. It is a pseudoenantiomer that is commonly employed in malaria therapy. Cinchonine is also used as an organocatalyst in many asymmetric reactions.

Application

Cinchonine can be used:
  • As a substrate in the study of supercritical fluid chromatography (SFC) parameters in pharmaceutical analysis.
  • To prepare possible butyrylcholinesterase inhibitors.

pictograms

Exclamation mark
GHS07

signalword

Warning

hcodes

H302,H317

Hazard Classifications

Acute Tox. 4 Oral - Skin Sens. 1A

Storage Class

11 - Combustible Solids

wgk

WGK 1

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
SDBB5542
STBL0665
STBK8251
STBK0347
STBJ3021

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Gold nanoparticles decorated with a cinchonine organocatalyst: application in the asymmetric alpha-amination of beta-ketoesters
Santacruz L, et al.
New. J. Chem., 38(2), 636-640 (2014)
Vibrational analysis of cinchona alkaloids in the solid state and aqueous solutions
Roman M, et al.
Journal of Raman Spectroscopy, 46(11), 1041-1052 (2015)
Anita Bosak et al.
PloS one, 13(10), e0205193-e0205193 (2018-10-06)
This paper describes the synthesis and anticholinesterase potency of Cinchona-based alkaloids; ten quaternary derivatives of cinchonines and their corresponding pseudo-enantiomeric cinchonidines. The quaternization of quinuclidine moiety of each compound was carried out with groups diverse in their size: methyl, benzyl
Chemistry and biology of Cinchona alkaloids
Kacprzak K
Natural Products, 605-641 (2013)
Amandine Dispas et al.
Journal of pharmaceutical and biomedical analysis, 125, 339-354 (2016-04-23)
Nowadays, supercritical fluid chromatography is commonly presented as a promising alternative technique in the field of separation sciences. Nevertheless the selection of chromatographic conditions and sample preparation of pharmaceutical compounds remain a challenge and peak distortion was previously highlighted. The
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