Cinchonine
Appearance
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Names | |
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IUPAC name | |
Systematic IUPAC name
(S)-[(2R,4S,5R)-5-Ethenyl-1-azabicyclo[2.2.2]octan-2-yl](quinolin-4-yl)methanol | |
Identifiers | |
3D model (JSmol)
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89689 | |
ChEBI | |
ChEMBL | |
ChemSpider | |
ECHA InfoCard | 100.003.850 |
EC Number |
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KEGG | |
PubChem CID
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UNII | |
CompTox Dashboard (EPA)
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Properties | |
C19H22N2O | |
Molar mass | 294.39 g/mol |
Melting point | 260-263 |
Hazards | |
GHS labelling: | |
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Warning | |
H302, H317, H332 | |
P261, P264, P270, P271, P272, P280, P301+P312, P302+P352, P304+P312, P304+P340, P312, P321, P330, P333+P313, P363, P501 | |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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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.
It is a GLP-1 receptor agonist and therefore has potential as a possible treatment for obesity, type 2 diabetes, and non-alcoholic fatty liver disease.[3]
References
[edit]- ^ "Common Chemistry - Substance Details - 118-10-5 : Cinchonan-9-ol, (9S)-". commonchemistry.org. Retrieved 22 May 2020.
- ^ IUPAC Chemical Nomenclature and Structure Representation Division (2013). "P-(Appendix 3, p. 1517)". In Favre, Henri A.; Powell, Warren H. (eds.). Nomenclature of Organic Chemistry: IUPAC Recommendations and Preferred Names 2013. IUPAC–RSC. ISBN 978-0-85404-182-4.
- ^ Xue, Huan; Xing, Hao-Jie; Wang, Bin; Fu, Chao; Zhang, Yu-Shan; Qiao, Xi; Guo, Chao; Zhang, Xiao-Li; Hu, Bin; Zhao, Xin; Deng, Li-Jiao; Zhu, Xiao-Chan; Zhang, Yi; Liu, Yun-Feng (11 May 2023). "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. 17: 1417–1432. doi:10.2147/DDDT.S404055. PMC 10184894.