27370
Cinchonine
crystallized, ≥98.0% (NT)
Synonym(s):
NSC 6176
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About This Item
Empirical Formula (Hill Notation):
C19H22N2O
CAS Number:
Molecular Weight:
294.39
UNSPSC Code:
12352104
NACRES:
NA.22
PubChem Substance ID:
EC Number:
204-234-6
Beilstein/REAXYS Number:
89689
MDL number:
Quality Level
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
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.
signalword
Warning
hcodes
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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Chemistry and biology of Cinchona alkaloids
Kacprzak K
Natural Products, 605-641 (2013)
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
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)