Cinchonine

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.

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
3D model (JSmol)
89689
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.003.850
EC Number
  • 204-234-6
KEGG
PubChem CID
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 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
C19H22N2O
Molar mass 294.39 g/mol
Melting point 260-263
Hazards
GHS labelling:
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).
Y verify (what is YN ?)
Infobox references

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.

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