Page 76 - phytochemistry general program

HOH2C H3C H3C
NH
NCH3 NCH3

NH NH NH

Elymoclavine Festaclavine Agroclavine

HOH2C OH HO
HOH2C

NCH3

NH NH

Chanoclavine Penniclavine

Lysergic acid amides .2
Simple lysergic acid amides .1
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-(or laevo)

lysergic acid with 2-aminopropanol.

Ergonovinine (or ergometrinine) is its diastereomer (at carbon No 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).

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