is a
Chemical Compound whose structural skeleton is contained in a diverse range of
Alkaloids and a few
Psychedelic Drugs (
Ololiuhqui ,
LSD ). Substances derived from ergoline are used clinically for the purpose of
Vasoconstriction and in the treatment of
Migraine and
Parkinson's Disease , some are implicated in the disease
Ergotism . Ergometrine and ergotamine are listed as Table I precursors under the
United Nations Convention Against Illicit Traffic In Narcotic Drugs And Psychotropic Substances {Link without Title} .
There are three main classes of ergoline derivatives, the water-soluble
Amide s of , the water-insoluble '''ergo
Peptide ''' alkaloids, and the '''clavine''' group.
The prototype of this class is
- (d-lysergic acid amide, LSA, LAA, LA-111)
- --- IUPAC Name : 9,10-didehydro-6-methylergoline-8beta-carboxamide
- --- CAS Number : 478-94-4
Other important members include:
- (ergobasine)
- --- INN : ergometrine
- --- IUPAC Name : (8beta(S))-9,10-didehydro-N-(2-hydroxy-1-methylethyl)-6-methyl-ergoline-8-carboxamide
- --- CAS Number : 60-79-7
- (ME-277)
- --- INN : methylergometrine
- --- IUPAC Name : (8beta(S))-9,10-didehydro-N-(1-(hydroxymethyl)propyl)-6-methyl-ergoline-8-carboxamide
- --- CAS Number : 113-42-8
- (UML-491)
- --- INN : methysergide
- --- IUPAC Name : (8beta)-9,10-didehydro-N-(1-(hydroxymethyl)propyl)-1,6-dimethyl-ergoline-8-carboxamide
- --- CAS Number : 361-37-5
- (d-lysergic acid diethylamide; LSD-25)
- --- INN : lysergamide
- --- IUPAC Name : (8beta)-9,10-didehydro-N,N-diethyl-6-methyl-ergoline-8-carboxamide
- --- CAS Number : 50-37-3
The relationship between these compounds is summarized in the following
Structural Formula and table of substitutions.
These compounds have a tri
Peptide structure attached to the basic ergoline ring, in the same location as the
Amide group of the lysergic acid derivatives. Some of the important are summarized below. In addition to the following ergopeptides, a commonly encountered term is '''ergotoxine''', which refers to a mixture of equal proportions of ergocristine, ergocornine and ergocryptine.
-
- --- IUPAC Name : Ergotaman-3',6',18-trione, 12'-hydroxy-2'-methyl-5'-(phenylmethyl)-, (5'-alpha)- (9CI)
- --- CAS Number : 113-15-5
-
- --- IUPAC Name : Ergotaman-3',6',18-trione, 12'-hydroxy-2'-(1-methylethyl)-5'-(phenylmethyl)-, (5'-alpha)-
- --- CAS Number : 511-08-0
-
- --- IUPAC Name : Ergotaman-3',6',18-trione, 12'-hydroxy-2',5'-bis(1-methylethyl)-, (5'-alpha)-
- --- CAS Number : 564-36-3
-
- --- IUPAC Name :Ergotaman-3',6',18-trione, 12'-hydroxy-2'-(1-methylethyl)-5'-(2-methylpropyl)-, (5'alpha)- (9CI)
- --- CAS Number : 511-09-1
- ( INN )
- --- IUPAC Name : Ergotaman-3',6',18-trione, 2-bromo-12'-hydroxy-2'-(1-methylethyl)-5'-(2-methylpropyl)-, (5'alpha)-
- --- CAS Number : 25614-03-3
-
- --- IUPAC Name : Ergotaman-3',6',18-trione, 12'-hydroxy-2'-methyl-5'-(1-methylethyl)-, (5'alpha)-
- --- CAS Number : 2873-38-3
A variety of modifications to the basic ergoline are seen in nature, for example , '''elymoclavine''', '''lysergol'''. Those deriving from '''dimethylergoline''' are referred to as '''clavines'''.
Some synthetic ergoline derivatives do fall easily into any of the above groups. Some examples are:
Ergoline
Alkaloid s were first isolated from
Ergot , a fungus that infects grain and causes the disease
Ergotism . Ergot also has a long history of medicinal use, which led to attempts to characterize its activity
Chemically . This began in
1907 with the isolation by G. Barger and F. H. Carrin of ergotoxine, so-named since it appeared to exhibit more of the
Toxic ity of ergot than its
Therapeutic qualities. With the isolation of in
1918 by A. Stoll came the first therapeutic use of isolated
Ergoline alkaloids.
With the determination of the basic . Newer synthetic ergolines used for Parkinson's disease include and '''lisuride'''. Perhaps the most famous ergoline derivative of all is the
Psychedelic Drug '''
LSD '''.
In
1960 ,
Albert Hofmann (discoverer of methergine, dihydroergotamine, Hydergine and LSD) delivered a speech that was to cause shockwaves of incredulity and even disbelief in the scientific community. Ergoline alkaloids, previously only known from the lower
Fungi , had been found in two species of
Flowering Plant s. These were the
Mexican species ''
Rivea Corymbosa '' and ''
Ipomoea Violacea '' of the
Convolvulaceae (morning glory) family, the seeds of which were identified as the psychedelic plant drugs known as "
Ololiuhqui " and "
Tlitliltzin ". Hofmann's result was later confirmed by other studies. The principal alkaloids in the seeds are ergine and its
Optical Isomer isoergine, with several other lysergic acid derivatives and clavines present in lesser amounts. The
Hawaii an species ''
Argyreia Nervosa '' was later found to include similar alkaloids. It is possible, though not proven, that
Ergine and/or isoergine are responsible for the
Hallucinogen ic effects.