Quinine

• CAT Number: R007524
• CAS Number: 130-95-0
• Molecular Formula: C20H24N2O2
• Molecular Weight: 324.42
• Purity: ≥95%
• Storage: -80°C
• IUPAC Name: (R)-[(2S,4S,5R)-5-ethenyl-1-azabicyclo[2.2.2]octan-2-yl]-(6-methoxyquinolin-4-yl)methanol
• InChI: InChI=1S/C20H24N2O2/c1-3-13-12-22-9-7-14(13)10-19(22)20(23)16-6-8-21-18-5-4-15(24-2)11-17(16)18/h3-6,8,11,13-14,19-20,23H,1,7,9-10,12H2,2H3/t13-,14-,19-,20+/m0/s1
• InChIKey: LOUPRKONTZGTKE-WZBLMQSHSA-N
• SMILES: COC1=CC2=C(C=CN=C2C=C1)C(C3CC4CCN3CC4C=C)O

Quinine (CAS 130-95-0) is an optical isomer of Quinidine and an anti-malarial, skeletal, muscle relaxant.

Overview of Clinical Research

Quinine has been granted for its orphan drug status in Falciparum malaria. 

Reference

1:A case of acute interstitial nephritis and granulomatous hepatitis induced by ingesting quinine. Katsuma A, Shibata M, Katsuki T, Imai E, Tada M, Hinoshita F.CEN Case Rep. 2015 May;4(1):76-80. doi: 10.1007/s13730-014-0143-0. Epub 2014 Aug 29. PMID: 28509275 Free PMC Article
2:Re-evaluation of the steady-state self-quenching constant of quinine bisulfate from fluorescence measurements in transmission geometry. Krimer N, Mirenda M.Methods Appl Fluoresc. 2017 May 12. doi: 10.1088/2050-6120/aa72a9. [Epub ahead of print] PMID: 28497773
3:Long term quinine for muscle cramps may increase death risk. Wise J.BMJ. 2017 May 11;357:j2236. doi: 10.1136/bmj.j2236. No abstract available. PMID: 28495864
4:Association Between Long-term Quinine Exposure and All-Cause Mortality. Fardet L, Nazareth I, Petersen I.JAMA. 2017 May 9;317(18):1907-1909. doi: 10.1001/jama.2017.2332. No abstract available. PMID: 28492890
5:First-trimester artemisinin derivatives and quinine treatments and the risk of adverse pregnancy outcomes in Africa and Asia: A meta-analysis of observational studies. Dellicour S, Sevene E, McGready R, Tinto H, Mosha D, Manyando C, Rulisa S, Desai M, Ouma P, Oneko M, Vala A, Rupérez M, Macete E, Menéndez C, Nakanabo-Diallo S, Kazienga A, Valéa I, Calip G, Augusto O, Genton B, Njunju EM, Moore KA, d/'Alessandro U, Nosten F, Ter Kuile F, Stergachis A.PLoS Med. 2017 May 2;14(5):e1002290. doi: 10.1371/journal.pmed.1002290. eCollection 2017 May. PMID: 28463996 Free PMC Article
6:A highly enantioselective Friedel-Crafts reaction of 3,5-dimethoxylphenol with nitroolefins mediated by a bifunctional quinine derived thiourea catalyst. Han X, Ye C, Chen F, Chen Q, Wang Y, Zeng X.Org Biomol Chem. 2017 Apr 18;15(16):3401-3407. doi: 10.1039/c7ob00372b. PMID: 28382349
7:Enhanced fed-batch production of pyrroloquinoline quinine in Methylobacillus sp. CCTCC M2016079 with a two-stage pH control strategy. Si Z, Machaku D, Wei P, Huang L, Cai J, Xu Z.Appl Microbiol Biotechnol. 2017 Apr 3. doi: 10.1007/s00253-017-8259-8. [Epub ahead of print] PMID: 28374050
8:Changes in sucrose and quinine taste reactivity patterns in infant rat pups after exposure to the other tastant. Suárez AB, Ifrán MC, Pautassi RM, Kamenetzky GV.Appetite. 2017 Jul 1;114:259-264. doi: 10.1016/j.appet.2017.03.040. Epub 2017 Mar 29. PMID: 28363812
9:Quinine bonded to superficially porous particles for high-efficiency and ultrafast liquid and supercritical fluid chromatography. Patel DC, Breitbach ZS, Yu J, Nguyen KA, Armstrong DW.Anal Chim Acta. 2017 Apr 22;963:164-174. doi: 10.1016/j.aca.2017.02.005. Epub 2017 Feb 20. PMID: 28335970
10:Fixed food eruption caused by quinine in a 54-year-old female patient. Sommer C, Zikeli M, Müllegger R.J Dtsch Dermatol Ges. 2017 Apr;15(4):449-450. doi: 10.1111/ddg.12893. Epub 2017 Mar 15. No abstract available. PMID: 28296085