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Compound Summary

General Compound Information

Quinine

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Description

Quinine is a cinchona alkaloid that is cinchonidine in which the hydrogen at the 6-position of the quinoline ring is substituted by methoxy. It has a role as an antimalarial, a muscle relaxant and a non-narcotic analgesic. It is a conjugate base of a quinine(1+). It derives from a hydride of an (8S)-cinchonan.

Synonyms

Quinine; 130-95-0; Chinine; Chinin; (-)-Quinine;

6'-Methoxycinchonidine;(8S,9R)-Quinine;Qualaquin;quinine sulfate;(R)-(-)-quinine;Quinine, Anhydrous;chininum;quinina;Quinoline alkaloid;Rezquin;Chininum purum;quinine bisulphate;(8S,9R)-6'-Methoxycinchonan-9-ol;Aflukin;CHEBI:15854;6-Methoxycinchonine;A7V27PHC7A;Quinine sulphate;Cinchonan-9-ol, 6'-methoxy-, (8a,9R)-;DTXSID0044280;Quinine anhydrous;(R)-(6-methoxyquinolin-4-yl)((2S,4S,8R)-8-vinylquinuclidin-2-yl)methanol;(R)-[(2S,4S,5R)-5-ethenyl-1-azabicyclo[2.2.2]octan-2-yl]-(6-methoxyquinolin-4-yl)methanol;NSC-192949;Coco-Quinine;WR297608;NSC 5362;Cinchonan-9-ol, 6'-methoxy-, (8alpha,9R)-;MFCD00198096;6'-Methoxycinchonan-9-ol;Quinine, tannate;Chinin [German];Cinchonan-9-ol, 6'-methoxy-, (8alpha,9R)-(+/-)-;DTXCID60819897;Quinineanhydrous;GNF-Pf-506;(R)-(6-Methoxyquinolin-4-yl)((1S,2S,4S,5R)-5-vinylquinuclidin-2-yl)methanol;(R)-[(2S,4S,5R)-1-Aza-5-vinylbicyclo[2.2.2]-oct-2-yl](6-methoxyquinolin-4-yl)methanol;(R)-[(2S,4S,5R)-5-ethenyl-1-azabicyclo[2.2.2]octan-2-yl](6-methoxyquinolin-4-yl)methanol;72402-53-0;CAS-130-95-0;6'-Methoxycinchonine;Quinine [BAN:NF];CHEMBL170;Quinine tannate [USP];Cinchonan-9-ol, 6'-methoxy-, (8.alpha.,9R)-;UNII-26MX5YAL2R;UNII-A7V27PHC7A;NSC 192949;Quinsan;(8-alpha,9R)-6'-Methoxycinchonan-9-ol;(R)-(-)-Quinine, 6-methoxycinchonidine;CCRIS 5755;NSC192949;HSDB 2501;(-)quinine;NCGC00166281-01;QI9;EINECS 205-003-2;EINECS 215-805-4;Dentojel (Bisulfate heptathydrate);Biquinate (Bisulfate heptathydrate);Quinine, 90%;(3alpha,8alpha,9R)-6'-methoxycinchonan-9-ol;NSC667852;(9R)-6'-methoxy-8alpha-cinchonan-9-ol;Quine (2:1 Sulfate salt, dihydrate);QUININE [VANDF];QUININE [HSDB];QUININE [INCI];(8.alpha.,9R)-6'-Methoxycinchonan-9-ol;Quinamm (2:1 Sulfate salt), dihydrate;Quinsan (2:1 Sulfate salt), dihydrate;QUININE [MI];QUININE [MART.];QUININE [WHO-DD];Epitope ID:131786;EC 205-003-2;SCHEMBL27031;CHININUM PURUM [HPUS];Cinchonan-9-ol, 6'-methoxy-;GTPL2510;Cinchonan-9-ol, 6'-methoxy-, (8.alpha.,9R)-, sulfate;HMS2089E05;2-Quinuclidinemethanol, alpha-(6-methoxy-4-quinolyl)-5-vinyl-;ACT08125;STR03990;ZINC3831404;Tox21_112389;BDBM50367247;s4495;AKOS017343662;Tox21_112389_1;DB00468;NCGC00274071-01;EN300-258513;O12066;AB00375052-11;AB00375052-12;AB00375052_13;Cinchonan-9-ol, 6'-methoxy-, (8-alpha,9R)-;Q189522;Quinine, certified reference material, TraceCERT(R);BRD-K07940445-003-01-2;Q27166273;Z2235811384;(R)-(6-methoxy-4-quinolyl)-[(2S,4S,5R)-5-vinylquinuclidin-2-yl]methanol;(R)-(6-methoxyquinolin-4-yl)((2S,4S,5R)-5-vinylquinuclidin-2-yl)methanol;(1R)-(6-methoxyquinolin-4-yl)((2S,4S,5R)-5-vinylquinuclidin-2-yl)methanol;(5-ethenyl-1-azabicyclo[2.2.2]octan-2-yl)-(6-methoxy-4-quinolinyl)methanol;Quinine, suitable for fluorescence, anhydrous, >=98.0% (dried material, NT);(alphaR)-alpha-[(4S)-5beta-Vinyl-1-azabicyclo[2.2.2]octane-2alpha-yl]-6-methoxyquinoline-4-methanol;(R)-[(1S,2S,4S,5R)-5-ethenyl-1-azabicyclo[2.2.2]octan-2-yl](6-methoxyquinolin-4-yl)methanol;(R)-[(4S,5R,7S)-5-ethenyl-1-azabicyclo[2.2.2]octan-7-yl]-(6-methoxyquinolin-4-yl)methanol;

FlavorDB ID

4210

PUBCHEM ID

Molecular Weight

324.4 Molecular Formula

C20H24N2O2

Openeye Can Smiles

COC1=CC2=C(C=CN=C2C=C1)C(C3CC4CCN3CC4C=C)O

IUPAC Inchikey

LOUPRKONTZGTKE-WZBLMQSHSA-N

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Toxicity Summary
Link to the Distributed Structure-Searchable Toxicity (DSSTox) Database
Quinine is a documented causative agent of drug induced thrombocytopenia (DIT). Thrombocytopenia is a low amount of platelets in the blood. Quinine induces production of antibodies against glycoprotein (GP) Ib-IX complex in the majority of cases of DIT, or more rarely, the platelet-glycoprotein complex GPIIb-IIIa. Increased antibodies against these complexes increases platelet clearance, leading to the observed thrombocytopenia.
Source: DrugBank or Hazardous Substances Data Bank (HSDB)

EFSA's chemical Hazards Database : OpenFoodTox
This compound is found in OpenFoodTox with the name: Quinine

Reference point : Defined point on an experimental dose–response relationship for the critical effect. This term is synonymous to Point of departure (USA). Reference points include the lowest or no observed adverse effect level (LOAEL/NOAEL) or benchmark dose lower confidence limit (BDML), used to derive a reference value or Margin of Exposure in human and animal health risk assessment. In the ecological area, these include lethal dose (LD50), effect concentration (EC5/ECx), no (adverse) effect concentration/dose (NOEC/NOAEC/NOAED), no (adverse) effect level (NEL/NOAEL), hazard concentration (HC5/HCx) derived from a Species Sensitivity Distributions (SSD) for the ecosystem (EFSA Scientific Committee,2018). Citation: DOI 10.5281/zenodo.4740174

Reference point information of this compound is not available!

Reference Value

Reference Value : The estimated maximum dose (on a body mass basis) or the concentration of an agent to which an individual may be exposed over a specified period without appreciable risk. Reference values are established by applying an uncertainty factor to the reference point. Examples of reference values in human health include acceptable daily intake (ADI) for food and feed additives, and pesticides, tolerable upper intake levels (UL) for vitamins and minerals, and tolerable daily intake (TDI) for contaminants and food contact materials. For acute effects and operators, the acute reference dose (ARfD) and the acceptable operator exposure level (AOEL). In animal health and the ecological area, these include safe feed concentrations and the Predicted no effect concentration (PNEC) respectively (EFSA Scientific Committee, 2018). Citation: DOI 10.5281/zenodo.4740174

Reference value information of this compound is not available!

Genotoxicity

Genotoxicity information of this compound is not available!

EFSA Outputs

EFSA outputs information of this compound is not available!

Receptors

Receptor	REFERENCE	EC50 [µM]	Effective Concentration [µM]
TAS2R4	details	Activated	10.00
TAS2R7	details	Activated	10.00
TAS2R10	details	Activated	10.00
TAS2R14	details	Activated	10.00
TAS2R31	details	Activated	10.00
TAS2R39	details	Activated	10.00
TAS2R40	details	Activated	10.00
TAS2R43	details	Activated	10.00
TAS2R46	details	Activated	10.00

Consensus Spectra

Spectrum Type	Spectrum View	Description	Polarity
Experimental LCMS	view	LCMS_Positive	positive

Content

Compound Summary

Quinine

Description

Synonyms

Quinine; 130-95-0; Chinine; Chinin; (-)-Quinine;

FlavorDB ID

4210

PUBCHEM ID

3034034

Molecular Weight

324.4

Molecular Formula

C20H24N2O2

Openeye Can Smiles

COC1=CC2=C(C=CN=C2C=C1)C(C3CC4CCN3CC4C=C)O

IUPAC Inchikey

LOUPRKONTZGTKE-WZBLMQSHSA-N

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Content

Compound Summary

Quinine

Description

Synonyms

Quinine; 130-95-0; Chinine; Chinin; (-)-Quinine;

FlavorDB ID

4210

PUBCHEM ID

3034034

Molecular Weight

324.4

Molecular Formula

C20H24N2O2

Openeye Can Smiles

COC1=CC2=C(C=CN=C2C=C1)C(C3CC4CCN3CC4C=C)O

IUPAC Inchikey

LOUPRKONTZGTKE-WZBLMQSHSA-N

Network

Shown in network

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OpenFoodTox: component Quinine

Reference Details

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GC-MS Spectrum