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{{More citations needed|date=January 2021}}

{{chembox
{{chembox
| Watchedfields = changed
| verifiedrevid = 420135264
| verifiedrevid = 420135264
| Name = Cinchonine
| Name = Cinchonine
| ImageFile = Cinchonine.png
| ImageFile = Cinchonine.svg
| ImageName = Cinchonine
| ImageSize = 180
| ImageName = Cinchonine
| IUPACName = (9''S'')-Cinchonan-9-ol<ref>{{cite web |title=Common Chemistry - Substance Details - 118-10-5 : Cinchonan-9-ol, (9S)- |url=https://commonchemistry.org/ChemicalDetail.aspx?ref=118-10-5 |website=commonchemistry.org |accessdate=22 May 2020}}</ref><ref>{{BlueBook2013|rec=(Appendix 3, p. 1517)}}</ref>
| IUPACName = Cinchonine
| SystematicName = (''S'')-[(2''R'',4''S'',5''R'')-5-Ethenyl-1-azabicyclo[2.2.2]octan-2-yl](quinolin-4-yl)methanol
| Section1 = {{Chembox Identifiers
| Section1 = {{Chembox Identifiers
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 746392
| ChemSpiderID = 746392
| UNII_Ref = {{fdacite|correct|FDA}}
| PubChem = 90454
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = V43X79NZCD
| UNII = V43X79NZCD
| 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
| 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
| InChIKey = KMPWYEUPVWOPIM-LSOMNZGLBY
| InChIKey = KMPWYEUPVWOPIM-LSOMNZGLBY
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 496893
| ChEMBL = 496893
| EC_number = 204-234-6
⚫
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| ChEBI = 27509
⚫
| StdInChI = 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
| Beilstein = 89689
⚫
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
⚫
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
⚫
| StdInChIKey = KMPWYEUPVWOPIM-LSOMNZGLSA-N
⚫
| StdInChI = 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
⚫
| CASNo_Ref = {{cascite|correct|CAS}}
⚫
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
⚫
| CASNo = 118-10-5
⚫
| StdInChIKey = KMPWYEUPVWOPIM-LSOMNZGLSA-N
⚫
| KEGG_Ref = {{keggcite|correct|kegg}}
⚫
| CASNo_Ref = {{cascite|correct|CAS}}
⚫
| KEGG = C06528
⚫
| CASNo = 118-10-5
⚫
| SMILES = n2c1c(cccc1)c(cc2)[C@H](O)[C@H]3N4CC[C@@H](C3)[C@@H](C=C)C4
⚫
| KEGG_Ref = {{keggcite|correct|kegg}}
⚫
}}
⚫
| KEGG = C06528
⚫
| SMILES = O[C@H]([C@H]1C[C@@H]2CC[N@]1C[C@@H]2C=C)c1ccnc2ccccc12
}}

| Section2 = {{Chembox Properties
| Section2 = {{Chembox Properties
| Formula = C<sub>19</sub>H<sub>22</sub>N<sub>2</sub>O
| Formula = C<sub>19</sub>H<sub>22</sub>N<sub>2</sub>O
| MolarMass = 294.39 g/mol
| MolarMass = 294.39 g/mol
| Density =
| Density =
| MeltingPt =
| MeltingPt = 260-263
| BoilingPt =
| BoilingPt =
}}
}}
| Section7 = {{Chembox Hazards
| GHSPictograms = {{GHS07}}
| GHSSignalWord = Warning
| HPhrases = {{H-phrases|302|317|332}}
| PPhrases = {{P-phrases|261|264|270|271|272|280|301+312|302+352|304+312|304+340|312|321|330|333+313|363|501}}
⚫
}}
}}
}}


'''Cinchonine''' is an [[alkaloid]] with molecular formula C<sub>19</sub>H<sub>22</sub>N<sub>2</sub>O used in [[asymmetric synthesis]] in organic chemistry. It is a stereoisomer and pseudo-[[enantiomer]] of [[cinchonidine]].
'''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]].<ref>{{cite journal |last1=Xue |first1=Huan |last2=Xing |first2=Hao-Jie |last3=Wang |first3=Bin |last4=Fu |first4=Chao |last5=Zhang |first5=Yu-Shan |last6=Qiao |first6=Xi |last7=Guo |first7=Chao |last8=Zhang |first8=Xiao-Li |last9=Hu |first9=Bin |last10=Zhao |first10=Xin |last11=Deng |first11=Li-Jiao |last12=Zhu |first12=Xiao-Chan |last13=Zhang |first13=Yi |last14=Liu |first14=Yun-Feng |title=Cinchonine, a Potential Oral Small-Molecule Glucagon-Like Peptide-1 Receptor Agonist, Lowers Blood Glucose and Ameliorates Non-Alcoholic Steatohepatitis |journal=Drug Design, Development and Therapy |date=11 May 2023 |volume=17 |pages=1417–1432 |doi=10.2147/DDDT.S404055 |url=https://www.dovepress.com/cinchonine-a-potential-oral-small-molecule-glucagon-like-peptide-1-rec-peer-reviewed-fulltext-article-DDDT |language=English|doi-access=free |pmc=10184894 }}</ref>

== References ==
<references />

⚫
[[Category:Secondary alcohols]]
⚫
[[Category:Vinyl compounds]]
⚫
[[Category:Quinoline alkaloids]]
[[Category:Quinuclidine alkaloids]]
[[Category:GLP-1 receptor agonists]]


⚫
[[Category:Alkaloids]]
⚫
[[Category:Quinolines]]
⚫
[[Category:Alcohols]]
[[Category:Quinuclidines]]
[[Category:Alkenes]]


{{alkaloid-stub}}
[[ar:سينكونين]]
[[fr:Cinchonine]]
[[sv:Cinkonin]]

Latest revision as of 20:28, 2 January 2024

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

[edit]
  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.


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