Simple lysergic acid amides

Lysergic acid methylcarbinolamide (XXXVI) crystallizes from chloroform in long prisms, mp 135° (dec.), [a]f,° + 29° (c = 1.0 in dimethyl-formamide). The alkaloid, which was isolated together with ergine and erginine from saprophytic cultures of Claviceps paspali (69), easily decomposes in a weak acid solution to form ergine and acetaldehyde. 

Ergometrine (XXXVII) crystallizes from ethyl acetate in massive tetrahedrons, mp 162° (dec.). From chloroform, in which the alkaloid is 

In 1935 ergometrine was discovered in four different laboratories almost simultaneously and described under four different names (74, 75, 76, 77). Although the names ergometrine and ergobasine have remained in use in Europe, ergonovine was adopted in the USA as the official nomenclature for the specific uterotonic ergot alkaloid. 

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A representative of the simple lysergic acid amide derivatives is the semisynthetic diethylamide, LSD (lysergic acid diethylamide), which has a questionable reputation. Although LSD is not really a natural product, the discovery of its powerful hallucinogenic properties by Hofmann in the 1940s led to the development of the broad field of psychopharmacology. 

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. 

Fig. 4.7 Biosynthesis of ergohne alkaloids IV. Presumable formation of simple lysergic acid amides occurring in Claviceps spp. and certain convolvulaceous species lysergoyl adenylate is transformed to an enzyme-linked lysergoyl-L-alanine by a peptide synthetase different to LPS the low-molecular direct precursor of ergometrine released from the enzyme might be the corresponding aldehyde which in turn could be reduced in the last step the homologous lysergic acid a-hydroxyethylamide might be produced in a similar manner...

This group includes simple lysergic acid amides and peptide ergot alkaloids. Most of these substances are directly used in pharmaceutical preparations. However, reports referring to their biotransformation are scarce. 

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