Difference between revisions of "Quinine"

From Sciencemadness Wiki
Jump to: navigation, search
(Created page with "{{distinguish|quinone}} {{Chembox | Name = Quinine | Reference = | IUPACName = (R)-(6-Methoxyquinolin-4-yl)[(1S,2S,4S,5R)-5-vinylquinuclidin-2-yl]methanol | PIN = | Systematic...")
 
 
(11 intermediate revisions by one other user not shown)
Line 8: Line 8:
 
| OtherNames = Chinine<br>Qualaquin<br>Quinate<br>Quinbisul
 
| OtherNames = Chinine<br>Qualaquin<br>Quinate<br>Quinbisul
 
<!-- Images -->
 
<!-- Images -->
| ImageFile =  
+
| ImageFile = Quinine structure.png
| ImageSize =  
+
| ImageSize = 250
 
| ImageAlt =  
 
| ImageAlt =  
 
| ImageName =  
 
| ImageName =  
| ImageFile1 =  
+
| ImageCaption = Quinine structure
| ImageSize1 =  
+
| ImageFile1 = Quinine_sulfate_solution.jpg
 +
| ImageSize1 = 250
 
| ImageAlt1 =  
 
| ImageAlt1 =  
 
| ImageName1 =  
 
| ImageName1 =  
 +
| ImageCaption1 = Fluorescence of an acidic aq. solution
 
| ImageFile2 =  
 
| ImageFile2 =  
 
| ImageSize2 =  
 
| ImageSize2 =  
Line 53: Line 55:
 
| BoilingPt_ref =  
 
| BoilingPt_ref =  
 
| BoilingPt_notes = Decomposes
 
| BoilingPt_notes = Decomposes
| Density =  
+
| Density = 1.2 g/cm<sup>3</sup>
 
| Formula = C<sub>20</sub>H<sub>24</sub>N<sub>2</sub>O<sub>2</sub>
 
| Formula = C<sub>20</sub>H<sub>24</sub>N<sub>2</sub>O<sub>2</sub>
 
| HenryConstant =  
 
| HenryConstant =  
Line 66: Line 68:
 
| pKb =  
 
| pKb =  
 
| Solubility = 0.05 g/100 ml (15 °C)
 
| Solubility = 0.05 g/100 ml (15 °C)
| SolubleOther =  
+
| SolubleOther = Soluble in [[carbon disulfide]], [[chloroform]], [[ethanol]]<br>Slightly soluble in [[glycerol]]<br>Insoluble in [[ammonia]], [[petroleum ether]]
| Solvent =  
+
| Solubility1 = 1.25 g/100 ml
 +
| Solvent1 = benzene
 +
| Solubility2 = 83.3 g/100 ml
 +
| Solvent2 = chloroform
 +
| Solubility3 = 0.4 g/100 ml
 +
| Solvent3 = diethyl ether
 +
| Solubility4 = 125 g/100 ml
 +
| Solvent4 = ethanol
 +
| Solubility5 = 5 g/100 ml
 +
| Solvent5 = glycerol
 
| Taste = Extremely bitter
 
| Taste = Extremely bitter
 
| VaporPressure = 1.54·10<sup>-10</sup> mmHg at 25 °C
 
| VaporPressure = 1.54·10<sup>-10</sup> mmHg at 25 °C
Line 110: Line 121:
 
   }}
 
   }}
 
}}
 
}}
'''Quinine''' is a used as medication to treat malaria and babesiosis.
+
'''Quinine''' is an [[alkaloid]] isolated from Cinchona bark, used as medication to treat malaria and babesiosis.
  
 
==Properties==
 
==Properties==
Line 119: Line 130:
  
 
===Physical===
 
===Physical===
Quinine is a colorless or white solid, with a potent bitter taste.
+
Quinine is a colorless or white solid, with a potent bitter taste. As freebase, it is insoluble in [[water]], but more soluble in other organic solvents, such as [[chloroform]] or [[ethanol]].
 +
 
 +
===Chromatgraphic===
 +
A variety of TLC conditions has been published to distinguish the cinchona alkaloids. Suitable systems on silica gel 60 are dichloromethane/diethylamine, v/v, 9/1, or chloroform/methanol/conc. ammonia solution, 17 + 2.8 + 0.2. Note that in order to observe the fluorescence of quinine, it may be necessary to spray the plate with ethanolic sulfuric acid.<ref name="illu" />
  
 
==Availability==
 
==Availability==
Quinine is sold online.
+
Quinine is sold online. Often, it is sold in salt form, as sulfate.<ref>https://www.ebay.com/p/Quinine-Sulfate-Dihydrate-99-titration-Powder-50g/1648490218</ref>
  
 
Tonic water has small amounts of quinine, though not enough for it to be an economical source.
 
Tonic water has small amounts of quinine, though not enough for it to be an economical source.
  
 
==Preparation==
 
==Preparation==
Quinine is best extracted from plant than synthesized from precursors.
+
Quinine is best extracted from Cinchona tree bark than synthesized from precursors.
 +
 
 +
For extraction, the ground bark is mixed with slaked lime and some water and left to soak (it may be adviseable to carefully dry the mix?), followed by a soxhlet extraction with toluene.<ref>LambdaSyn, "Chinin aus Chinarinde", [https://www.lambdasyn.org/synfiles/chinin.html https://www.lambdasyn.org/synfiles/chinin.html]</ref> Purification is archived via the sulfate, because the (quinineH)<sub>2</sub>SO<sub>4</sub> salt has the lowest solubility of the cinchona alkaloid sulfates (1 g per 800 g water).<ref name="illu">lemmi, "Das Prochinin-Rätsel und die Chemie der Chinaalkaloide", [https://illumina-chemie.de/viewtopic.php?t=4527 https://illumina-chemie.de/viewtopic.php?t=4527]</ref>
  
 
==Projects==
 
==Projects==
 
*Compound collecting
 
*Compound collecting
 +
*Bitter taste mixtures
 
*Tonic water
 
*Tonic water
 
*Make fluorescent drinks
 
*Make fluorescent drinks
Line 138: Line 155:
 
==Handling==
 
==Handling==
 
===Safety===
 
===Safety===
Exposure to quinine is known to cause abnormal heart rhythms.
+
Exposure to large amounts of quinine is known to cause abnormal heart rhythms.
  
 
===Storage===
 
===Storage===
Line 155: Line 172:
 
[[Category:Aromatic compounds]]
 
[[Category:Aromatic compounds]]
 
[[Category:Biologically-derived compounds]]
 
[[Category:Biologically-derived compounds]]
 +
[[Category:Fluorescent materials]]
 +
[[Category:Readily available chemicals]]

Latest revision as of 18:36, 5 March 2024

Not to be confused with quinone.
Quinine
Quinine structure.png
Quinine structure
Quinine sulfate solution.jpg
Fluorescence of an acidic aq. solution
Names
IUPAC name
(R)-(6-Methoxyquinolin-4-yl)[(1S,2S,4S,5R)-5-vinylquinuclidin-2-yl]methanol
Other names
Chinine
Qualaquin
Quinate
Quinbisul
Properties
C20H24N2O2
Molar mass 324.42 g/mol
Appearance White solid
Odor Odorless
Density 1.2 g/cm3
Melting point 177 °C (351 °F; 450 K)
Boiling point Decomposes
0.05 g/100 ml (15 °C)
Solubility Soluble in carbon disulfide, chloroform, ethanol
Slightly soluble in glycerol
Insoluble in ammonia, petroleum ether
Solubility in benzene 1.25 g/100 ml
Solubility in chloroform 83.3 g/100 ml
Solubility in diethyl ether 0.4 g/100 ml
Solubility in ethanol 125 g/100 ml
Solubility in glycerol 5 g/100 ml
Vapor pressure 1.54·10-10 mmHg at 25 °C
Hazards
Safety data sheet Sigma-Aldrich
Lethal dose or concentration (LD, LC):
1,800 mg/kg (guinea pig, oral)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Quinine is an alkaloid isolated from Cinchona bark, used as medication to treat malaria and babesiosis.

Properties

Chemical

Quinine reacts with acids forming water soluble salts.

Quinine will slowly oxidize upon exposure to air over long periods of time, in both free and salt form, turning dark.

Physical

Quinine is a colorless or white solid, with a potent bitter taste. As freebase, it is insoluble in water, but more soluble in other organic solvents, such as chloroform or ethanol.

Chromatgraphic

A variety of TLC conditions has been published to distinguish the cinchona alkaloids. Suitable systems on silica gel 60 are dichloromethane/diethylamine, v/v, 9/1, or chloroform/methanol/conc. ammonia solution, 17 + 2.8 + 0.2. Note that in order to observe the fluorescence of quinine, it may be necessary to spray the plate with ethanolic sulfuric acid.[1]

Availability

Quinine is sold online. Often, it is sold in salt form, as sulfate.[2]

Tonic water has small amounts of quinine, though not enough for it to be an economical source.

Preparation

Quinine is best extracted from Cinchona tree bark than synthesized from precursors.

For extraction, the ground bark is mixed with slaked lime and some water and left to soak (it may be adviseable to carefully dry the mix?), followed by a soxhlet extraction with toluene.[3] Purification is archived via the sulfate, because the (quinineH)2SO4 salt has the lowest solubility of the cinchona alkaloid sulfates (1 g per 800 g water).[1]

Projects

  • Compound collecting
  • Bitter taste mixtures
  • Tonic water
  • Make fluorescent drinks
  • Anti-malaria drug
  • Demonstration of triboluminescence

Handling

Safety

Exposure to large amounts of quinine is known to cause abnormal heart rhythms.

Storage

Quinine should be kept in plastic or glass bottles, in dark places.

Disposal

Can be safely poured down the drain or in trash.

References

  1. 1.0 1.1 lemmi, "Das Prochinin-Rätsel und die Chemie der Chinaalkaloide", https://illumina-chemie.de/viewtopic.php?t=4527
  2. https://www.ebay.com/p/Quinine-Sulfate-Dihydrate-99-titration-Powder-50g/1648490218
  3. LambdaSyn, "Chinin aus Chinarinde", https://www.lambdasyn.org/synfiles/chinin.html

Relevant Sciencemadness threads