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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
EC Number:
204-234-6
Beilstein/REAXYS Number:
89689
UNSPSC Code:
12352104
NACRES:
NA.22
PubChem Substance ID:
57648242
MDL number:
MFCD00064372
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Quality Segment

100

assay

≥98.0% (NT)

form

powder

optical activity

[α]20/D +225±5°, c = 0.5% in ethanol

quality

crystallized

manufacturer/tradename

ECACC

impurities

~15% dihydrocinchonine (HPLC)

mp

260-263 °C

functional group

hydroxyl

SMILES string

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

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

InChI key

KMPWYEUPVWOPIM-QAMTZSDWSA-N

Gene Information

human ... CYP2D6(1565)

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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