cinchonine

Cinchonine is an alkaloid found in Cinchona officinalis. It is used in asymmetric synthesis in organic chemistry. It is a stereoisomer and pseudo-enantiomer of cinchonidine.

In the Vinony graph

Within Vinony's link graph, cinchonine is referenced by 113 other articles, and connects out to International Standard Book Number, digital object identifier and chemical formula.

It sits within the topics Chembox having GHS data, Chembox image size set and ECHA InfoCard ID from Wikidata.

Its subject is documented across 20 Wikipedia language editions.

Chemical data

Formula: C19H22N2O
Molecular weight: 294.4 g/mol
IUPAC name: (S)-[(2R,4S,5R)-5-ethenyl-1-azabicyclo[2.2.2]octan-2-yl]-quinolin-4-ylmethanol
SMILES: C=C[C@H]1CN2CC[C@H]1C[C@@H]2[C@H](C3=CC=NC4=CC=CC=C34)O
InChIKey: KMPWYEUPVWOPIM-QAMTZSDWSA-N
XLogP: 2.7
Polar surface area: 36.4 Å²
H-bond donors: 1
H-bond acceptors: 3
Formal charge: 0

via PubChem

Research

286 papers

Cinchonine: A Versatile Pharmacological Agent Derived from Natural Cinchona Alkaloids.Current topics in medicinal chemistry · 2024
Cinchonine-induced cell death in pancreatic cancer cells by downregulating RRP15.Cell biology international · 2023
Cinchonine and cinchonidine alleviate cisplatin-induced ototoxicity by regulating PI3K-AKT signaling.CNS neuroscience & therapeutics · 2024
Cinchonine, a Potential Oral Small-Molecule Glucagon-Like Peptide-1 Receptor Agonist, Lowers Blood Glucose and Ameliorates Non-Alcoholic Steatohepatitis.Drug design, development and therapy · 2023
Enhancing the Stability, Solubility, and Antioxidant Activity of Cinchonine through Pharmaceutical Cocrystallization.Pharmaceutical research · 2024

via PubMed

Wikidata facts

Mass: 294.17321332399996

Show 9 more facts

canonical SMILES: C=CC1CN2CCC1CC2C(C3=CC=NC4=CC=CC=C34)O
chemical formula: C₁₉H₂₂N₂O
found in taxon: Artemisia maritima
Commons category: Cinchonine
subject has role: antimalarial
isomeric SMILES: C=C[C@H]1CN2CC[C@H]1C[C@@H]2[C@H](C3=CC=NC4=CC=CC=C34)O
described by source: New International Encyclopedia
melting point: 258
has characteristic: bitterness

Sources (7)

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Encyclopedic overview

1 sections

Contents

References

Cinchonine is an alkaloid found in Cinchona officinalis. It is used in asymmetric synthesis in organic chemistry. It is a stereoisomer and pseudo-enantiomer of cinchonidine.

It is structurally similar to quinine, an antimalarial drug.

Excerpted from Wikipedia’s “cinchonine” article, available under the CC BY-SA 4.0 licence.