Lysergic acid amide, structure

The compounds 12,14 and 15 can be prepared from parent lysergic acid amides by bromination with NBS or PHT, but not the compounds of the type 12. The latter structure is very sensitive and under these circumstances only degradation products were obtained. Besides it was necessary to use much milder reagent, e.g. bromine bonded onto polymeric matrix with polyvinylpyrrolidone or polyvinylpyridine structure (29) ... 

Figure 2 Ergot alkaloids schematic structure of the ergoline ring system, of D-lysergic acid amides, and of agroclavine as an example for the "simple" clavine alkaloids. (Modified from Tudzynski et al., 2001.)...

Ergot alkaloids are usually divided into three main structural types two of which include a lysergic acid amide moiety (Fig. 4.2) ... 

Surprisingly, members of all three structural types, i.e., ergopeptines, simple lysergic acid amides, and clavines turned out to be constituents of certain convolvulaceous species. Furthermore, this is also true for aU four groups of clavines. 

Table 1 Structures of the naturally occurring d-lysergic acid amides arranged on a combinatorial basis considering the multiplicity of amide-bond forming building blocks in their side chains...

On the basis of their structural differences, the ergot alkaloids may be divided into two main groups one group to include all lysergic acid derivatives of the acid amide type, and the other to include the so-called clavine alkaloids. Further structural groups may be recognized within these main groups, as is shown by Tables I and II. 

Mother Nature s bounty is then squirreled off to the lab site for the biochemical phase of the process - the isolation of the lysergic alkaloids. Here one or more of a series of alkaloids are freed from the very complex plant matrix and hopefully isolated in a pure form. These alkaloids all have one thing in common - they are amides of lysergic acid. See the structures of the major naturally occurring amides pictured below ... 

Fig. 2. Structures of lysergic acid and some lysergyl amides and clavines.

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