Cinchonine

Cinchonine
	Cinchonine
Names
	IUPAC name (9S)-Cinchonan-9-ol
	Systematic IUPAC name (S)-[(2R,4S,5R)-5-Ethenyl-1-azabicyclo[2.2.2]octan-2-yl](quinolin-4-yl)methanol
Identifiers
CAS Number	118-10-5 ;
3D model (JSmol)	Interactive image;
Beilstein Reference	89689
ChEBI	CHEBI:27509;
ChEMBL	ChEMBL496893 ;
ChemSpider	746392 ;
ECHA InfoCard	100.003.850
EC Number	204-234-6;
KEGG	C06528 ;
PubChem CID	90454;
UNII	V43X79NZCD ;
CompTox Dashboard (EPA)	DTXSID6045082 ;
	InChI 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 Key: KMPWYEUPVWOPIM-LSOMNZGLSA-N ; 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;
	SMILES O[C@H]([C@H]1C[C@@H]2CC[N@]1C[C@@H]2C=C)c1ccnc2ccccc12;
Properties
Chemical formula	C19H22N2O
Molar mass	294.39 g/mol
Melting point	260-263
Hazards
	GHS labelling:
Pictograms
Signal word	Warning
Hazard statements	H302, H317, H332
Precautionary statements	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). verify (what is ?) Infobox 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 was first extracted from cinchona bark by the Portuguese physician Gomez in 1812. Liebig in 1830 made an elemental analysis and found C₂₀H₂₂N₂O, close to the correct value of C₁₉H₂₂N₂O^[3]

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.^[4]

References

↑ "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.
↑ Usselman, Melvyn; Rocke, Alan; Reinhart, Christina; Foulser, Kelly (January 2005). "Restaging Liebig: A Study in the Replication of Experiments". Annals of Science. 62 (1): 1–55. doi:10.1080/00033790410001711922. ISSN 0003-3790.
↑ 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. PMID 37197367.

This article about an alkaloid is a stub. You can help Wikipedia by adding missing information.

[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] Usselman, Melvyn; Rocke, Alan; Reinhart, Christina; Foulser, Kelly (January 2005). "Restaging Liebig: A Study in the Replication of Experiments". Annals of Science. 62 (1): 1–55. doi:10.1080/00033790410001711922. ISSN 0003-3790.

[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. PMID 37197367.

[1]

[2]

[3]

[4]