Cinchonine

Cinchonine
Cinchonine
Names
IUPAC name
(9S)-Cinchonan-9-ol[1][2]
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)
89689
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.003.850 Edit this at Wikidata
EC Number
  • 204-234-6
KEGG
UNII
  • 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 checkY
    Key: KMPWYEUPVWOPIM-LSOMNZGLSA-N checkY
  • InChI=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
  • O[C@H]([C@H]1C[C@@H]2CC[N@]1C[C@@H]2C=C)c1ccnc2ccccc12
Properties
C19H22N2O
Molar mass 294.39 g/mol
Melting point 260-263
Hazards
GHS labelling:
GHS07: Exclamation mark
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).
checkY verify (what is checkY☒N ?)

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

  1. ^ "Common Chemistry - Substance Details - 118-10-5 : Cinchonan-9-ol, (9S)-". commonchemistry.org. Retrieved 22 May 2020.
  2. ^ 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.
  3. ^ 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.


Stub icon

This article about an alkaloid is a stub. You can help Wikipedia by expanding it.