From Wikipedia, the free encyclopedia
Cinchonine
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Names
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IUPAC name
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Systematic IUPAC name
(S)-[(2R,4S,5R)-5-Ethenyl-1-azabicyclo[2.2.2]octan-2-yl](quinolin-4-yl)methanol
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Identifiers
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89689
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ChEBI
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ChEMBL
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ChemSpider
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ECHA InfoCard
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100.003.850
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EC Number
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KEGG
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UNII
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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 YKey: KMPWYEUPVWOPIM-LSOMNZGLSA-N YInChI=1/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 Key: KMPWYEUPVWOPIM-LSOMNZGLBY
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O[C@H]([C@H]1C[C@@H]2CC[N@]1C[C@@H]2C=C)c1ccnc2ccccc12
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Properties
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C19H22N2O
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Molar mass
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294.39 g/mol
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Melting point
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260-263
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Hazards
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GHS labelling:
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Warning
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H302,
H317,
H332
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P261,
P264,
P270,
P271,
P272,
P280,
P301+P312,
P302+P352,
P304+P312,
P304+P340,
P312,
P321,
P330,
P333+P313,
P363,
P501
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Except where otherwise noted, data are given for materials in their
standard state (at 25 °C [77 °F], 100 kPa).
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Chemical compound
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
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^
"Common Chemistry - Substance Details - 118-10-5 : Cinchonan-9-ol, (9S)-". commonchemistry.org. Retrieved 22 May 2020.
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^ 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.
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^ 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.