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Cinchona Alkaloids
Quinic acid
HO
H3CO
Quinine
in
N
H3CO
differs
HO
pair
N
Quinidine
the
Properties:
Quinine is very slightly soluble in H2O, soluble in
ethanol, chloroform, ether, benzene and other organic
solvents.
Quinine is a diacidic base. It forms 2 types of sulfates:
Quinine monosulfate (neutral and H O insoluble).
2
Quinine bisulfate
(acidic and H2O soluble).
Precipitate (monosulphate)
Quinine
Hot water, Na2CO3
Quinine
Ether layer
Quinidine & Cinchonidine
-HCl PH=7, Na, K Tart. salt
- filter
Precipitate
Filtrate
Cinchonidine tartrate
Quinidine tartrate
Aqueous layer
Cinchonine
1- Fluorescence test:
Solution of the alkaloid in oxygenated acids (e.g H 2SO4, HNO3 or
phosphoric acid) blue fluorescence (+ ve with quinine and quinidine).
2- Thalleoquine test:
Aqueous solution of the alkaloidal salt + Br2 /H2O (few drops till the
appearance of yellow color) + NH4OH emerald green color
(+ ve with quinine and quinidine).
Uses:
Isoquinoline Alkaloids
1- Ipecacuanha Alkaloids
Occurrence:
Ipecac is the dried roots and rhizomes of Cephalis ipecacuanha (Brazilian
ipecacuanha) or Cephalis acuminata (Cartagena or Panama ipecacuanha)
Fam. Rubiaceae.
It contains several alkaloids (2 2.5 %), mainly emetine (50- 70 % of total
alkaloids), with cephaline and psychotrine.
MeO
RO
MeO
OMe
N
OMe
H
N
R = Me Emetine
R=H
Cephaline
HO
OMe
OMe
N
H
N
Psychotrine
Emetine:
It is non phenolic and levorotatory.
It contains 2 basic nitrogens.
Cephaline:
It is phenolic and levorotatory.
It gives emetine on methylation with (CH3)2 SO4.
Psychotrine:
Occurs as yellow prisms.
It is phenolic and gives cephaline on reduction.
It gives emetine on reduction followed by methylation.
Isolation of Ipeca
alkaloids:
Powdered
root and rhizome
- Ext. alcohol,Conc., lead acetate.
- Filtration
Filtrate
Alkaloidal bases and salts
- Evap., dil. HCl & Filtration
Residue
Non-alkaloidal sub.
Ether layer
Emetine
Aqueous layer
(Psychotrine)
Ether layer
(Cephaline)
Uses:
2- Curare Alkaloids
Occurrence:
Curare or South American arrow poison is the dried crude extract, obtained
mainly from Chondrodendron tomentosum (Menispermaceae) and certain
Strychnos species, (Loganiaceae).
MeO
N
Me
OH H
O
Me
Me
H
N+
OH
OMe
Properties:
d-tubocurarine (4ary alkaloid) is freely soluble in H2O. It is a phenolic
dextrorotatory alkaloid. It is a bis-benzyltetrahydroisoquinoline
alkaloid.
Tests:
Uses: