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cinchonine
Sign in to saveCinchonine 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.
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 Ų
- 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
~1 min read
Encyclopedic overview
1 sectionsContents
- 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.