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 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

^ "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.

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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
CAS Number	118-10-5^Y
3D model (JSmol)	Interactive image
Beilstein Reference	89689
ChEBI	CHEBI:27509
ChEMBL	ChEMBL496893^Y
ChemSpider	746392^Y
ECHA InfoCard	100.003.850
EC Number	204-234-6
KEGG	C06528^Y
PubChem CID	90454
UNII	V43X79NZCD^Y
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^Y Key: KMPWYEUPVWOPIM-LSOMNZGLSA-N^Y 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). Y verify (what is ^YN ?) Infobox references