Ergoline

175-183 ° C ( mixture of stereoisomers )

• Slightly soluble in chloroform, benzene, ethanol; moderately soluble in diethyl ether; insoluble in water, petroleum ether

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Ergoline is a polycyclic nitrogen-containing organic chemical compound. This substance was first described in 1937 by Walter A. Jacobs and R. Gordon Gould Jr.. She is the backbone of most of the ergot alkaloids and many other fully or partially synthetically produced substances. From the ergoline Ergoline structurally derived substances are referred to and used in medicine for the treatment of migraine, Parkinson 's disease and of cardiovascular diseases. The name was from the - spread mainly in the English language - the name ergot sclerotia of the fungus Claviceps ergot derived.

Representation

The synthesis of ergoline based on the construction of a tetracyclic ring system starting from naphthalic. In a first reaction step is reacted according to naphthalic Leuck, Perkins and Whitmore to 3 -nitro-1 -naphthoic acid, which is reduced in the presence of iron ( II) sulfate and ammonia to give 3 -amino-1 -naphthoic acid. In a Skraup synthesis, the bicyclic 3 -amino-1 -naphthoic acid is enhanced by acid-catalyzed addition of acrolein from glycerol is a ring of 5,6- benzoquinoline - 7-carboxylic acid. With the addition of fuming nitric acid, the 5,6- benzoquinoline - 7-carboxylic acid is nitrated to 3 -nitro -5 ,6- benzoquinoline - 7-carboxylic acid. The reaction product is reduced in the presence of iron ( II) sulphate in an alkaline medium to the amine. After the addition of hydrochloric acid, the ring closure to the corresponding lactam, the tetracyclic 3'-amino -5 ,6- benzoquinoline 7- carbonsäurelactam. Finally, the lactam is reduced with elemental sodium in butanol to the final product ergoline.

Properties

Chemical Properties

Ergoline is a white powdery crystalline substance that readily dissolves in ethanol, chloroform and benzene. In the presence of Ehrlich's reagent or Van Urk reagent Ergin is an intense color reaction. A deep blue - violet color can be observed in the presence of Keller's reagent.

Stereochemistry

Ergoline has two stereocenters. Thus, there are computationally 4 stereoisomers of the ergoline. All naturally occurring and all therapeutically used derivatives of ergoline have a 5R configuration.