Ergoline

Structural formula
General
Surname	Ergoline
other names	(6a R ) -4,6,6a, 7,8,9,10,10a-octahydroindolo [4,3- fg ] quinoline; (all- R ) -4,6,6a, 7,8,9,10,10a-octahydroindolo [4,3- fg ] quinoline;
Molecular formula	C 14 H 16 N 2
External identifiers / databases
PubChem	6857537
Wikidata	Q424432
properties
Molar mass	212.29 g mol −1
Physical state	firmly
Melting point	175–183 ° C (mixture of stereoisomers)
solubility	Easily soluble in chloroform , benzene , ethanol ; moderately soluble in diethyl ether ; insoluble in water, petroleum ether ;
safety instructions
GHS hazard labeling ; no classification available
GHS hazard labeling ; no classification available
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Ergolin is a polycyclic , nitrogen- containing organic chemical compound . This substance was first described in 1937 by Walter A. Jacobs and R. Gordon Gould Jr. It is the basic structure of the majority of ergot alkaloids and numerous other fully or partially synthetically produced substances. Substances that are structurally derived from ergoline are called ergolines and are used in medicine to treat migraines , Parkinson's disease and cardiovascular diseases . The name was derived from the term ergot for sclerotia of the ergot fungus Claviceps, which is mainly used in the English-speaking world .

presentation

The synthesis of ergoline is based on the structure of a tetracyclic ring system based on naphthalic acid . In a first reaction step, naphthalic acid is converted to 3-nitro-1-naphthoic acid according to Leuck, Perkins and Whitmore, which is reduced to 3-amino-1-naphthoic acid in the presence of iron (II) sulfate and ammonia . In a Skraup synthesis , the bicyclic 3-amino-1-naphthoic acid is expanded by an acid-catalyzed addition of acrolein from glycerol to form 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 to the amine in the presence of iron (II) sulfate in an alkaline medium. After the addition of hydrochloric acid , the ring closes to give the corresponding lactam , the tetracyclic 3'-amino-5,6-benzoquinoline-7-carboxylic acid lactam . Finally, the lactam is reduced with elemental sodium in butanol to the end product ergoline.

properties

Chemical properties

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

Stereochemistry

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

Individual evidence

↑ ^a ^b ^c ^d ^e ^f Jacobs WA, Gould Jr. RG: The ergot alkaloids: XII. The synthesis of substances related to lyseric acid . In: J. Biol. Chem . 120, No. 1, 1937, pp. 141-150.
^ WA Jacobs, RG Gould: THE SYNTHESIS OF SUBSTANCES RELATED TO LYSERGIC ACID. In: Science. Volume 85, Number 2201, March 1937, pp. 248-249, doi : 10.1126 / science.85.2201.248 , PMID 17841382 .
↑ This substance has either not yet been classified with regard to its hazardousness or a reliable and citable source has not yet been found.

[Jacobs_&_Gould_Jr._(1937)-1] ↑ ^a ^b ^c ^d ^e ^f Jacobs WA, Gould Jr. RG: The ergot alkaloids: XII. The synthesis of substances related to lyseric acid . In: J. Biol. Chem . 120, No. 1, 1937, pp. 141-150.

[2] WA Jacobs, RG Gould: THE SYNTHESIS OF SUBSTANCES RELATED TO LYSERGIC ACID. In: Science. Volume 85, Number 2201, March 1937, pp. 248-249, doi : 10.1126 / science.85.2201.248 , PMID 17841382 .

[NV-3] This substance has either not yet been classified with regard to its hazardousness or a reliable and citable source has not yet been found.