Page 80 - Phytochemistry 2 (06-PG 605)

Simple lysergic acid amides
All these are water-soluble alkaloids of relatively low
molecular weights as they are all amides of lysergic acid with
simple amines.
The simplest example of these amides is ergine (lysergic
acid amide itself) and erginine (isolysergic acid amide), that have
been isolated as naturally existing alkaloids (water soluble).
However, the most important member of this class is the
potent oxytocic alkaloid ergonovine (ergometrine) which is the
amide of l- lysergic acid with 2-aminopropanol.
Ergonovinine (or ergometrinine) is its diastereomer (at
carbon number 8, bearing the carboxyl group). So, the latter
alkaloid is the amide of d-lysergic acid with 2-aminopropanol.
Another example of this class is lysergic acid diethylamide
(LSD).

Name R1 R2 R3

Ergine H H H

Ergonovine H CH(CH3)CH2OH H

LSD H CH2CH3 CH2CH3

General Structure of Lysegic Amides

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