Record Information |
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Version | 1.0 |
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Creation date | 2010-04-08 22:05:14 UTC |
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Update date | 2018-05-29 00:33:54 UTC |
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Primary ID | FDB002087 |
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Secondary Accession Numbers | Not Available |
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Chemical Information |
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FooDB Name | Quinine |
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Description | It is used in tonics and bitter drinks
Quinine is a natural white crystalline alkaloid having antipyretic, antimalarial, analgesic, anti-inflammatory properties and a bitter taste. It is a stereoisomer of quinidine which, unlike quinine, is an anti-arrhythmic. Though it has been synthesized in the lab, the bark of the cinchona tree is the only known natural source of quinine. Quinine was the first effective treatment for malaria caused by Plasmodium falciparum, appearing in therapeutics in the 17th century. It remained the antimalarial drug of choice until the 1940s, when other drugs replaced it. |
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CAS Number | 130-95-0 |
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Structure | |
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Synonyms | Synonym | Source |
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(-)-Quinine | ChEBI | (8S,9R)-Quinine | ChEBI | (R)-(-)-Quinine | ChEBI | (R)-(6-Methoxyquinolin-4-yl)((2S,4S,8R)-8-vinylquinuclidin-2-yl)methanol | ChEBI | 6'-Methoxycinchonidine | ChEBI | Chinin | ChEBI | Chinine | ChEBI | Chininum | ChEBI | Quinina | ChEBI | Myoquin | MeSH | Surquina | MeSH | Biquinate | MeSH | Quinimax | MeSH | Quinine bisulfate | MeSH | Quinine sulfate | MeSH | Quinoctal | MeSH | Quinson | MeSH | Quinsul | MeSH | Bisulfate, quinine | MeSH | Hydrochloride, quinine | MeSH | Legatrim | MeSH | Quinamm | MeSH | Quinbisan | MeSH | Quinbisul | MeSH | Quinine lafran | MeSH | Quinine sulphate | MeSH | Quinine-odan | MeSH | Sulfate, quinine | MeSH | Sulphate, quinine | MeSH | Quindan | MeSH | Quinine hydrochloride | MeSH | Strema | MeSH | 6'-Methoxycinchonine | HMDB | Quinine, anhydrous | HMDB | Quinineanhydrous | HMDB | Quinoline alkaloid | HMDB | Aventis brand OF quinine bisulfate | MeSH, HMDB | Fawns and mcallan brand OF quinine sulfate | MeSH, HMDB | Foy brand OF quinine sulfate | MeSH, HMDB | Plough brand OF quinine sulfate | MeSH, HMDB | Fawns and mcallan brand OF quinine bisulfate | MeSH, HMDB | Hoechst brand OF quinine sulfate | MeSH, HMDB | Lafran brand OF quinine hydrochloride | MeSH, HMDB | Alphapharm brand OF quinine sulfate | MeSH, HMDB | Innotech brand OF quinine hydrochloride | MeSH, HMDB | Odan brand OF quinine sulfate | MeSH, HMDB | Prosana brand OF quinine bisulfate | MeSH, HMDB | (8-alpha,9R)-6'-Methoxycinchonan-9-ol | biospider | (8S,9R)-6'-Methoxycinchonan-9-ol | biospider | (R)-(-)-quinine | manual | (R)-(-)-Quinine, 6-methoxycinchonidine | biospider | α-(6-Methoxy-4-quinoyl)-5-vinyl-2-quinclidinemethanol | biospider | 6-Methoxy-quinolin | biospider | 6-Methoxycinchonine | biospider | 6'-Methoxycinchonan-9-ol, 9CI | db_source | Cinchonan-9-ol, 6'-methoxy- | biospider | Cinchonan-9-ol, 6'-methoxy-, (8α,9R)- | biospider | Cinchonan-9-ol, 6'-methoxy-, (8a,9R)- | biospider | Cinchonan-9-ol, 6'-methoxy-, (8alpha,9R)- | biospider |
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Predicted Properties | |
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Chemical Formula | C20H24N2O2 |
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IUPAC name | (R)-[(1S,2S,4S,5R)-5-ethenyl-1-azabicyclo[2.2.2]octan-2-yl](6-methoxyquinolin-4-yl)methanol |
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InChI Identifier | 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 |
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InChI Key | LOUPRKONTZGTKE-WZBLMQSHSA-N |
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Isomeric SMILES | [H][C@]1(C[C@@H]2CC[N@]1C[C@@H]2C=C)[C@H](O)C1=CC=NC2=CC=C(OC)C=C12 |
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Average Molecular Weight | 324.4168 |
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Monoisotopic Molecular Weight | 324.183778022 |
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Classification |
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Description | Belongs to the class of organic compounds known as cinchona alkaloids. These are alkaloids structurally characterized by the presence of the cinchonan skeleton, which consists of a quinoline linked to an azabicyclo[2.2.2]Octane moiety. |
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Kingdom | Organic compounds |
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Super Class | Alkaloids and derivatives |
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Class | Cinchona alkaloids |
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Sub Class | Not Available |
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Direct Parent | Cinchona alkaloids |
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Alternative Parents | |
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Substituents | - Cinchonan-skeleton
- 4-quinolinemethanol
- Quinoline
- Anisole
- Quinuclidine
- Alkyl aryl ether
- Aralkylamine
- Piperidine
- Pyridine
- Benzenoid
- Heteroaromatic compound
- 1,2-aminoalcohol
- Tertiary aliphatic amine
- Tertiary amine
- Secondary alcohol
- Ether
- Azacycle
- Organoheterocyclic compound
- Organooxygen compound
- Organonitrogen compound
- Organic nitrogen compound
- Hydrocarbon derivative
- Organopnictogen compound
- Amine
- Alcohol
- Organic oxygen compound
- Aromatic alcohol
- Aromatic heteropolycyclic compound
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Molecular Framework | Aromatic heteropolycyclic compounds |
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External Descriptors | |
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Ontology |
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Physiological effect | Health effect: |
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Disposition | Route of exposure: Biological location: |
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Role | Industrial application: |
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Physico-Chemical Properties - Experimental |
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Physico-Chemical Properties - Experimental | Property | Value | Reference |
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Physical state | Solid | |
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Physical Description | Not Available | |
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Mass Composition | C 74.05%; H 7.46%; N 8.63%; O 9.86% | DFC |
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Melting Point | Mp 177° (anhyd.) | DFC |
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Boiling Point | Not Available | |
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Experimental Water Solubility | 0.5 mg/mL at 15 oC | YALKOWSKY,SH & DANNENFELSER,RM (1992) |
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Experimental logP | 3.44 | HANSCH,C ET AL. (1995) |
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Experimental pKa | pKa2 4.21 (20°) | DFC |
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Isoelectric point | Not Available | |
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Charge | Not Available | |
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Optical Rotation | [a]D -158 (-145) (EtOH) | DFC |
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Spectroscopic UV Data | Not Available | |
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Density | Not Available | |
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Refractive Index | Not Available | |
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Spectra |
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Spectra | |
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EI-MS/GC-MS | Type | Description | Splash Key | View |
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Predicted GC-MS | Quinine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | splash10-0a4r-1901000000-8176add5a84f7ae1eb69 | Spectrum | Predicted GC-MS | Quinine, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive | splash10-05g0-7947000000-ee233460f7e7fbb00ca7 | Spectrum | Predicted GC-MS | Quinine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum |
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MS/MS | Type | Description | Splash Key | View |
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MS/MS | LC-MS/MS Spectrum - 60V, Positive | splash10-00ai-7930000000-eb63f68d11153566b027 | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 75V, Positive | splash10-00c0-7910000000-c0d16dda8d8a74dd1657 | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 45V, Positive | splash10-0059-5945000000-dff1a74853685996f965 | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 15V, Positive | splash10-004i-0009000000-4cf6c66b2059468cd1e3 | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 30V, Positive | splash10-004i-0009000000-d4367d77a81731ba3654 | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 60V, Positive | splash10-00ai-7930000000-94e16a407d113a547240 | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 45V, Positive | splash10-0059-5945000000-ddc4f19918fbae8ffe0c | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 90V, Positive | splash10-0fc0-6900000000-8bb456f41e7cb82dfcf9 | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 90V, Positive | splash10-0fc0-6900000000-f458cccf839df1d5239b | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 75V, Positive | splash10-00c0-7910000000-4b620f5ca762298602e7 | 2021-09-20 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-0a6r-0019000000-0f42379f2989cf204f72 | 2016-08-01 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0a4r-0729000000-5a0d8aa890e6c737bf45 | 2016-08-01 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0079-0920000000-70e4fed1a61c38cf53fb | 2016-08-01 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-00di-0109000000-e84ce15e838ff8ac33f6 | 2016-08-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-05fr-0229000000-b87ca7a53d952af7505e | 2016-08-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0540-0920000000-12d8977ce43e168f8453 | 2016-08-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-004i-0009000000-2125f5c1412244f91fb3 | 2021-09-24 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-004i-0109000000-1096d980c779fca1eb3f | 2021-09-24 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-00dr-0920000000-468db2e8e8941541468c | 2021-09-24 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-00di-0019000000-9c5f7ffbd0d69038e6da | 2021-09-24 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0abi-0914000000-92707d10764c62ebe320 | 2021-09-24 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0a4i-0900000000-9e1ce60a980eb9551f33 | 2021-09-24 | View Spectrum |
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NMR | Not Available |
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External Links |
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ChemSpider ID | 84989 |
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ChEMBL ID | CHEMBL170 |
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KEGG Compound ID | C06526 |
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Pubchem Compound ID | 3034034 |
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Pubchem Substance ID | Not Available |
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ChEBI ID | 15854 |
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Phenol-Explorer ID | Not Available |
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DrugBank ID | DB00468 |
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HMDB ID | HMDB14611 |
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CRC / DFC (Dictionary of Food Compounds) ID | CFC28-A:CFC28-A |
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EAFUS ID | Not Available |
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Dr. Duke ID | Not Available |
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BIGG ID | Not Available |
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KNApSAcK ID | C00002193 |
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HET ID | Not Available |
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Food Biomarker Ontology | Not Available |
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VMH ID | Not Available |
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Flavornet ID | Not Available |
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GoodScent ID | Not Available |
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SuperScent ID | Not Available |
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Wikipedia ID | Quinine |
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Phenol-Explorer Metabolite ID | Not Available |
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Duplicate IDS | Not Available |
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Old DFC IDS | Not Available |
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Associated Foods |
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Food | Content Range | Average | Reference |
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Food | | | Reference |
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Biological Effects and Interactions |
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Health Effects / Bioactivities | Not Available |
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Enzymes | Not Available |
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Pathways | Not Available |
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Metabolism | Not Available |
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Biosynthesis | Not Available |
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Organoleptic Properties |
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Flavours | Flavor | Citations |
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bitter |
- Ayana Wiener, Marina Shudler, Anat Levit, Masha Y. Niv. BitterDB: a database of bitter compounds. Nucleic Acids Res 2012, 40(Database issue):D413-419. DOI:10.1093/nar/gkr755
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Files |
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MSDS | show |
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References |
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Synthesis Reference | Not Available |
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General Reference | Not Available |
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Content Reference | |
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