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Cocaine (1855)
Quinine
Atropine Cocaine
4
Alkaloid Natural Products
oquinoline alkaloids
n isolert fra opium 1803 (Morpheus: gresk svngud)
HO O OH
Derivativeofphenantrene
II- Basicity:
R2-NH > R-NH2 > R3-N
Classification of alkaloids
Method II:
The powdered material is extracted with water or
aqueous alcohol containing dilute acid. Alkaloids
are extracted as their salts together with
accompanying soluble impurities.
Method III:
The powder is extracted with water soluble organic
solvents such as MeOH or EtOH which are good
solvents for both salts and free bases.
Plant material and solvent
Concentration Acidification
Alkalinization
a-(1/2)b+(1/2)c+1
EX:- C8H15NO,
8-15/2+1/2+1=2
NM
e
c) Reductive Degradation and Zinc Dust
Distillation:
In some cases the ring may be opened by heating
with hydiodic acid at 300C, e.g.,
HI
300C
Zinc dust distillation produces simple fragments from
which one can draw the conclusion about the carbon
framework of the alkaloid molecule.
(f) Dehydrogenation:
When an alkaloid is distilled with a catalyst such as
sulphur, selenium or palladium, dehydrogenation takes
place to form relatively simple and easy recognizable
products which provide a clue to the gross skeleton of the
alkaloid
During dehydrogenation, there occurs the elimination of
peripheral groups such as hydroxyl and Cmethyl.
(7) Synthesis:
reserpic acid on
fusion with potash
gives 5-hydroxy
isophthalic acid.
Now since one
The acidic of of isophthalic acid must
group
be the acidic group of the reserpic acid.
The hydroxyl and carboxyl groups in
reserpic acid are meta to each other.
Biosynthesis
of Alkaloid
BIOSYNTHESIS OF ALKALOIDS :
It is well established that alkaloids are derived from
Amino acid.
Pyridin
e
alkaloid