Record Information |
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Version | 2.0 |
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Created at | 2024-09-11 16:08:51 UTC |
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Updated at | 2024-09-11 16:08:52 UTC |
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NP-MRD ID | NP0338575 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | Quinine bisulfate |
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Description | Quinine bisulfate 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. 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. Quinine bisulfate is a very strong basic compound (based on its pKa). Quinine bisulfate is an odorless tasting compound. Outside of the human body,. It remained the antimalarial drug of choice until the 1940s, when other drugs replaced it. 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. |
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Structure | O.O.O.O.O.O.O.OS(O)(=O)=O.OS(O)(=O)=O.COC1=CC=C2N=CC=C([C@@H](O)[C@@H]3C[C@@H]4CC[N@]3C[C@@H]4C=C)C2=C1 InChI=1S/C20H24N2O2.2H2O4S.7H2O/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;2*1-5(2,3)4;;;;;;;/h3-6,8,11,13-14,19-20,23H,1,7,9-10,12H2,2H3;2*(H2,1,2,3,4);7*1H2/t13-,14-,19-,20+;;;;;;;;;/m0........./s1 |
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Synonyms | Value | Source |
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Quinine bisulfuric acid | Generator | Quinine bisulphate | Generator | Quinine bisulphuric acid | Generator |
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Chemical Formula | C20H42N2O17S2 |
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Average Mass | 646.6810 Da |
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Monoisotopic Mass | 646.19249 Da |
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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 bis(sulfuric acid) heptahydrate |
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Traditional Name | quinine bis(sulfuric acid) heptahydrate |
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CAS Registry Number | Not Available |
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SMILES | O.O.O.O.O.O.O.OS(O)(=O)=O.OS(O)(=O)=O.COC1=CC=C2N=CC=C([C@@H](O)[C@@H]3C[C@@H]4CC[N@]3C[C@@H]4C=C)C2=C1 |
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InChI Identifier | InChI=1S/C20H24N2O2.2H2O4S.7H2O/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;2*1-5(2,3)4;;;;;;;/h3-6,8,11,13-14,19-20,23H,1,7,9-10,12H2,2H3;2*(H2,1,2,3,4);7*1H2/t13-,14-,19-,20+;;;;;;;;;/m0........./s1 |
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InChI Key | QRINDWCWGOHSTN-FTCXZRKKSA-N |
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Experimental Spectra |
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| Not Available | Predicted Spectra |
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| Not Available | Chemical Shift Submissions |
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| Not Available | Species |
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Species of Origin | Not Available |
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Chemical Taxonomy |
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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
- Sulfuric acid
- Aralkylamine
- Benzenoid
- Pyridine
- Piperidine
- Heteroaromatic compound
- Organic sulfuric acid or derivatives
- 1,2-aminoalcohol
- Tertiary aliphatic amine
- Tertiary amine
- Secondary alcohol
- Organoheterocyclic compound
- Azacycle
- Ether
- Hydrocarbon derivative
- Organonitrogen compound
- Organooxygen compound
- Alcohol
- Organopnictogen compound
- Organic oxygen compound
- Organic nitrogen compound
- Amine
- Organic oxide
- Aromatic alcohol
- Aromatic heteropolycyclic compound
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Molecular Framework | Aromatic heteropolycyclic compounds |
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External Descriptors | Not Available |
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Physical Properties |
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State | Not Available |
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Experimental Properties | Property | Value | Reference |
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Melting Point | Not Available | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | Not Available | Not Available | LogP | Not Available | Not Available |
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Predicted Properties | |
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