Ergoline - AbsoluteAstronomy.com

Ergoline is a chemical compound

Chemical compound

A chemical compound is a pure chemical substance consisting of two or more different chemical elements that can be separated into simpler substances by chemical reactions. Chemical compounds have a unique and defined chemical structure; they consist of a fixed ratio of atoms that are held together...

whose structural skeleton is contained in a diverse range of alkaloids including a few psychedelic

Psychedelic

The term psychedelic is derived from the Greek words ψυχή and δηλοῦν , translating to "soul-manifesting". A psychedelic experience is characterized by the striking perception of aspects of one's mind previously unknown, or by the creative exuberance of the mind liberated from its ostensibly...

drugs

Psychoactive drug

A psychoactive drug, psychopharmaceutical, or psychotropic is a chemical substance that crosses the blood–brain barrier and acts primarily upon the central nervous system where it affects brain function, resulting in changes in perception, mood, consciousness, cognition, and behavior...

(e.g. lysergic acid

Lysergic acid

Lysergic acid, also known as D-lysergic acid and -lysergic acid, is a precursor for a wide range of ergoline alkaloids that are produced by the ergot fungus and some plants. Amides of lysergic acid, lysergamides, are widely used as pharmaceuticals and as psychedelic drugs...

and LSD

LSD

Lysergic acid diethylamide, abbreviated LSD or LSD-25, also known as lysergide and colloquially as acid, is a semisynthetic psychedelic drug of the ergoline family, well known for its psychological effects which can include altered thinking processes, closed and open eye visuals, synaesthesia, an...

). Ergoline derivatives are used clinically for the purpose of vasoconstriction

Vasoconstriction

Vasoconstriction is the narrowing of the blood vessels resulting from contraction of the muscular wall of the vessels, particularly the large arteries, small arterioles and veins. The process is the opposite of vasodilation, the widening of blood vessels. The process is particularly important in...

(5-HT₁

5-HT1 receptor

The 5-HT1 receptors are a subfamily of 5-HT receptors that bind the endogenous neurotransmitter serotonin . The 5-HT1 subfamily consists of five G protein-coupled receptors that are coupled to Gi/Go and mediate inhibitory neurotransmission, including 5-HT1A, 5-HT1B, 5-HT1D, 5-HT1E, and 5-HT1F...

receptor agonists—ergotamine) and in the treatment of migraines

Migraine

Migraine is a chronic neurological disorder characterized by moderate to severe headaches, and nausea...

(used with caffeine

Caffeine

Caffeine is a bitter, white crystalline xanthine alkaloid that acts as a stimulant drug. Caffeine is found in varying quantities in the seeds, leaves, and fruit of some plants, where it acts as a natural pesticide that paralyzes and kills certain insects feeding on the plants...

) and Parkinson's disease

Parkinson's disease

Parkinson's disease is a degenerative disorder of the central nervous system...

. Some ergoline alkaloids found in ergot

Ergot

Ergot or ergot fungi refers to a group of fungi of the genus Claviceps. The most prominent member of this group is Claviceps purpurea. This fungus grows on rye and related plants, and produces alkaloids that can cause ergotism in humans and other mammals who consume grains contaminated with its...

fungi are implicated in the condition ergotism

Ergotism

Ergotism is the effect of long-term ergot poisoning, traditionally due to the ingestion of the alkaloids produced by the Claviceps purpurea fungus which infects rye and other cereals, and more recently by the action of a number of ergoline-based drugs. It is also known as ergotoxicosis, ergot...

, which causes convulsive and gangrenous symptoms.

Uses

In addition to the naturally occurring ergonovine

Ergonovine

Ergometrine , is an ergoline derivative, and one of the primary ergot and morning glory alkaloids...

(used as an oxytocic) and ergotamine (a vasoconstrictor used to control migraine

Migraine

Migraine is a chronic neurological disorder characterized by moderate to severe headaches, and nausea...

), synthetic derivatives of importance are the oxytocic methergine, the anti-migraine drugs dihydroergotamine

Dihydroergotamine

Dihydroergotamine is an ergot alkaloid used to treat migraines. It is a derivative of ergotamine. It is administered as a nasal spray or injection and has an efficacy similar to that of sumatriptan...

and methysergide

Methysergide

Methysergide is a prescription drug used for prophylaxis of migraine headaches and is sold under the brand names Sansert and Deseril in 2 mg dosages.-Pharmacology:Methysergide interacts with serotonin receptors...

, hydergine (a mixture of dihydroergotoxine mesylates, INN

International Nonproprietary Name

An International Nonproprietary Name is the official nonproprietary or generic name given to a pharmaceutical substance, as designated by the World Health Organization...

: ergoline mesylates), and bromocriptine

Bromocriptine

Bromocriptine , an ergoline derivative, is a dopamine agonist that is used in the treatment of pituitary tumors, Parkinson's disease , hyperprolactinaemia, neuroleptic malignant syndrome, and type 2 diabetes.- Indications :Amenorrhea, female infertility, galactorrhea, hypogonadism, and acromegaly...

, used for numerous purposes including treatment of Parkinson's disease

Parkinson's disease

Parkinson's disease is a degenerative disorder of the central nervous system...

. Newer synthetic ergolines used for Parkinson's disease include pergolide

Pergolide

Pergolide is an ergoline-based dopamine receptor agonist used in some countries for the treatment of Parkinson's disease....

and lisuride

Lisuride

Lisuride is an antiparkinson agent of the iso-ergoline class, chemically related to the dopaminergic ergoline Parkinson's drugs. Lisuride is described as free base and as hydrogen maleate salt.Lisuride is used to lower prolactin and, in low doses, to prevent migraine attacks...

.

Perhaps the most famous ergoline derivative is the psychedelic

Psychedelic

drug

Psychoactive drug

LSD

. Ergometrine and ergotamine are included as table I precursors in the United Nations Convention Against Illicit Traffic in Narcotic Drugs and Psychotropic Substances

United Nations Convention Against Illicit Traffic in Narcotic Drugs and Psychotropic Substances

The United Nations Convention Against Illicit Traffic in Narcotic Drugs and Psychotropic Substances of 1988 is one of three major drug control treaties currently in force. It provides additional legal mechanisms for enforcing the 1961 Single Convention on Narcotic Drugs and the 1971 Convention on...

.

Ergolines can pass into breast milk

Breast milk

Breast milk, more specifically human milk, is the milk produced by the breasts of a human female for her infant offspring...

and should not be used during breastfeeding. They are uterine contractors that can increase the risk of miscarriage during pregnancy.

Natural occurrence

Ergoline alkaloids are found in lower fungi and two species of flowering plant

Flowering plant

The flowering plants , also known as Angiospermae or Magnoliophyta, are the most diverse group of land plants. Angiosperms are seed-producing plants like the gymnosperms and can be distinguished from the gymnosperms by a series of synapomorphies...

s: the Mexican

Mexico

The United Mexican States , commonly known as Mexico , is a federal constitutional republic in North America. It is bordered on the north by the United States; on the south and west by the Pacific Ocean; on the southeast by Guatemala, Belize, and the Caribbean Sea; and on the east by the Gulf of...

species Rivea corymbosa
Rivea corymbosa
Turbina corymbosa Turbina corymbosa Turbina corymbosa ((syn. Rivea corymbosa), the Christmas vine, is a species of morning glory, native throughout Latin America from Mexico in the North to Peru in the South and widely naturalised elsewhere. It is a perennial climbing vine with white flowers, often...

and Ipomoea violacea
Ipomoea violacea
Ipomoea violacea is a perennial species of Ipomoea that occurs throughout the tropics, growing in coastal regions. It is most commonly called 'Beach Moonflower' or 'Sea Moonflower' as the flowers open at night...

of the Convolvulaceae

Convolvulaceae

Convolvulaceae, known commonly as the bindweed or morning glory family, are a group of about 60 genera and more than 1,650 species of mostly herbaceous vines, but also trees, shrubs and herbs.- Description :...

(morning glory) family, the seeds of which were identified as the psychedelic plant drugs known as "ololiuhqui" and "tlitliltzin". 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

Hawaii

Hawaii is the newest of the 50 U.S. states , and is the only U.S. state made up entirely of islands. It is the northernmost island group in Polynesia, occupying most of an archipelago in the central Pacific Ocean, southwest of the continental United States, southeast of Japan, and northeast of...

an species Argyreia nervosa includes similar alkaloids. It is possible, though not proven, that ergine

Ergine

Ergine, also known as d-lysergic acid amide , d-lysergamide, and LA-111, is an alkaloid of the ergoline family that occurs in various species of vines of the Convolvulaceae and some species of fungi...

or isoergine are responsible for the hallucinogen

Psychedelics, dissociatives and deliriants

This general group of pharmacological agents can be divided into three broad categories: psychedelics, dissociatives, and deliriants. These classes of psychoactive drugs have in common that they can cause subjective changes in perception, thought, emotion and consciousness...

ic effects. There may be a fungal origin of the ergoline alkaloids also in the Convolvulaceae. Like the ergot alkaloids in some monocot plants, the ergoline alkaloids found in the plant Ipomoea asarifolia (Convolvulaceae) are produced by a seed-transmitted epiphytic

Epiphyte

An epiphyte is a plant that grows upon another plant non-parasitically or sometimes upon some other object , derives its moisture and nutrients from the air and rain and sometimes from debris accumulating around it, and is found in the temperate zone and in the...

clavicipitaceous fungus

Fungus

A fungus is a member of a large group of eukaryotic organisms that includes microorganisms such as yeasts and molds , as well as the more familiar mushrooms. These organisms are classified as a kingdom, Fungi, which is separate from plants, animals, and bacteria...

Ergopeptines

Peptide ergot alkaloids are ergoline derivatives that contain a tripeptide moiety, comprising proline and α-hydroxy-α-amino acids, linked in a cyclol formation with the carboxyl carbon of proline.

History

Ergoline alkaloid

Alkaloid

Alkaloids are a group of naturally occurring chemical compounds that contain mostly basic nitrogen atoms. This group also includes some related compounds with neutral and even weakly acidic properties. Also some synthetic compounds of similar structure are attributed to alkaloids...

s were first isolated from ergot

Ergot

, a fungus that infects grain and causes the disease ergotism

Ergotism

. Ergot also has a long history of medicinal use, which led to attempts to characterize its activity chemically

Chemistry

Chemistry is the science of matter, especially its chemical reactions, but also its composition, structure and properties. Chemistry is concerned with atoms and their interactions with other atoms, and particularly with the properties of chemical bonds....

. 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 toxicity of ergot than its therapeutic qualities. With the isolation of ergotamine in 1918 by A. Stoll came the first therapeutic use of isolated ergoline alkaloids.

With the determination of the basic chemical structure

Chemical structure

A chemical structure includes molecular geometry, electronic structure and crystal structure of molecules. Molecular geometry refers to the spatial arrangement of atoms in a molecule and the chemical bonds that hold the atoms together. Molecular geometry can range from the very simple, such as...

of the ergot alkaloids in the early 1930s, an era of intensive exploration of synthetic

Chemical synthesis

In chemistry, chemical synthesis is purposeful execution of chemical reactions to get a product, or several products. This happens by physical and chemical manipulations usually involving one or more reactions...

derivatives began.

Ergoline derivatives

There are 3 main classes of ergoline derivatives, the water-soluble amide

Amide

In chemistry, an amide is an organic compound that contains the functional group consisting of a carbonyl group linked to a nitrogen atom . The term refers both to a class of compounds and a functional group within those compounds. The term amide also refers to deprotonated form of ammonia or an...

s of lysergic acid
Lysergic acid
Lysergic acid, also known as D-lysergic acid and -lysergic acid, is a precursor for a wide range of ergoline alkaloids that are produced by the ergot fungus and some plants. Amides of lysergic acid, lysergamides, are widely used as pharmaceuticals and as psychedelic drugs...

, the water-insoluble ergopeptines (i.e., ergopeptides), and the clavine group.

Lysergic acid amides

Ergine
Ergine
Ergine, also known as d-lysergic acid amide , d-lysergamide, and LA-111, is an alkaloid of the ergoline family that occurs in various species of vines of the Convolvulaceae and some species of fungi...

(LSA, D-lysergic acid amide, LAA, LA-111)
- IUPAC name: 9,10-didehydro-6-methylergoline-8beta-carboxamide
- CAS number: 478-94-4
Ergonovine
Ergonovine
Ergometrine , is an ergoline derivative, and one of the primary ergot and morning glory alkaloids...

(ergobasine)
- INN
  International Nonproprietary Name
  An International Nonproprietary Name is the official nonproprietary or generic name given to a pharmaceutical substance, as designated by the World Health Organization...
  
  : ergometrine
- IUPAC name: (8beta(S))−9,10-didehydro-N-(2-hydroxy-1-methylethyl)−6-methyl-ergoline-8-carboxamide
- CAS number: 60-79-7
Methergine (ME-277)
- INN
  International Nonproprietary Name
  An International Nonproprietary Name is the official nonproprietary or generic name given to a pharmaceutical substance, as designated by the World Health Organization...
  
  : methylergometrine
- IUPAC name: (8beta(S))−9,10-didehydro-N-(1-(hydroxymethyl)propyl)−6-methyl-ergoline-8-carboxamide
- CAS number: 113-42-8
Methysergide
Methysergide
Methysergide is a prescription drug used for prophylaxis of migraine headaches and is sold under the brand names Sansert and Deseril in 2 mg dosages.-Pharmacology:Methysergide interacts with serotonin receptors...

(UML-491)
- INN
  International Nonproprietary Name
  An International Nonproprietary Name is the official nonproprietary or generic name given to a pharmaceutical substance, as designated by the World Health Organization...
  
  : methysergide
- IUPAC name: (8beta)−9,10-didehydro-N-(1-(hydroxymethyl)propyl)−1,6-dimethyl-ergoline-8-carboxamide
- CAS number: 361-37-5
LSD
LSD
Lysergic acid diethylamide, abbreviated LSD or LSD-25, also known as lysergide and colloquially as acid, is a semisynthetic psychedelic drug of the ergoline family, well known for its psychological effects which can include altered thinking processes, closed and open eye visuals, synaesthesia, an...

(D-lysergic acid diethylamide, LSD-25)
- INN
  International Nonproprietary Name
  An International Nonproprietary Name is the official nonproprietary or generic name given to a pharmaceutical substance, as designated by the World Health Organization...
  
  : lysergide
- IUPAC name: (8beta)−9,10-didehydro-N,N-diethyl-6-methyl-ergoline-8-carboxamide
- CAS number: 50-37-3
LSH (D-lysergic acid α-hydroxyethylamide)
- IUPAC name: 9,10-didehydro-N-(1-hydroxyethyl)-6-methylergoline-8-carboxamide
- CAS number: 3343-15-5

The relationship between these compounds is summarized in the following structural formula

Structural formula

The structural formula of a chemical compound is a graphical representation of the molecular structure, showing how the atoms are arranged. The chemical bonding within the molecule is also shown, either explicitly or implicitly...

and table of substitutions.

Name	R¹	R²	R³
Ergine Ergine Ergine, also known as d-lysergic acid amide , d-lysergamide, and LA-111, is an alkaloid of the ergoline family that occurs in various species of vines of the Convolvulaceae and some species of fungi...	H	H	H
Ergonovine Ergonovine Ergometrine , is an ergoline derivative, and one of the primary ergot and morning glory alkaloids...	H	CH(CH₃)CH₂OH	H
Methergine	H	CH(CH₂CH₃)CH₂OH	H
Methysergide Methysergide Methysergide is a prescription drug used for prophylaxis of migraine headaches and is sold under the brand names Sansert and Deseril in 2 mg dosages.-Pharmacology:Methysergide interacts with serotonin receptors...	CH₃	CH(CH₂CH₃)CH₂OH	H
LSD LSD Lysergic acid diethylamide, abbreviated LSD or LSD-25, also known as lysergide and colloquially as acid, is a semisynthetic psychedelic drug of the ergoline family, well known for its psychological effects which can include altered thinking processes, closed and open eye visuals, synaesthesia, an...	H	CH₂CH₃ Ethyl group In chemistry, an ethyl group is an alkyl substituent derived from ethane . It has the formula -C2H5 and is very often abbreviated -Et.Ethylation is the formation of a compound by introduction of the ethyl functional group, C2H5....	CH₂CH₃ Ethyl group In chemistry, an ethyl group is an alkyl substituent derived from ethane . It has the formula -C2H5 and is very often abbreviated -Et.Ethylation is the formation of a compound by introduction of the ethyl functional group, C2H5....

Peptide alkaloids
These compounds have a tripeptide

Peptide

Peptides are short polymers of amino acid monomers linked by peptide bonds. They are distinguished from proteins on the basis of size, typically containing less than 50 monomer units. The shortest peptides are dipeptides, consisting of two amino acids joined by a single peptide bond...

structure attached to the basic ergoline ring, in the same location as the amide

Amide

group of the lysergic acid derivatives. This tripeptide moiety contains an unusual cyclol

Cyclol

The cyclol hypothesis is the first structural model of a folded, globular protein. It was developed by Dorothy Wrinch in the late 1930s, and was based on three assumptions. Firstly, the hypothesis assumes that two peptide groups can be crosslinked by a cyclol reaction ; these crosslinks are...

bond >N-C(OH)< at the juncture between the two lactam

Lactam

A lactam is a cyclic amide. Prefixes indicate how many carbon atoms are present in the ring: β-lactam , γ-lactam , δ-lactam...

rings. Some of the important ergopeptines (also known as ergopeptides) are summarized below. In addition to the following ergopeptines, a commonly encountered term is ergotoxine, which refers to a mixture of equal proportions of ergocristine, ergocornine and ergocryptine.

Ergotamine
- IUPAC name: Ergotaman-3',6',18-trione, 12'-hydroxy-2'-methyl-5'-(phenylmethyl)-, (5'-alpha)- (9CI)
- CAS number: 113-15-5
Ergocristine
Ergocristine
Ergocristine is an ergopeptine and one of the ergot alkaloids.It was used as precursor in the manufacture of LSD as an alternative for the controlled substances ergotamine and ergometrine by various LSD manufacturers, including William Leonard Pickard...
- IUPAC name: Ergotaman-3',6',18-trione, 12'-hydroxy-2'-(1-methylethyl)−5'-(phenylmethyl)-, (5'-alpha)-
- CAS number: 511-08-0
Ergocornine
- IUPAC name: Ergotaman-3',6',18-trione, 12'-hydroxy-2',5'-bis(1-methylethyl)-, (5'-alpha)-
- CAS number: 564-36-3
Ergocryptine
Ergocryptine
Ergocryptine is an ergopeptine and one of the ergot alkaloids. It is often used to synthesis LSD, rather than ergotamine. It was the precursor being used by William Leonard Pickard in his clandestine LSD lab....
- IUPAC name:Ergotaman-3',6',18-trione, 12'-hydroxy-2'-(1-methylethyl)−5'-(2-methylpropyl)-, (5'alpha)- (9CI)
- CAS number: 511-09-1
Ergovaline
Ergovaline
Ergovaline is an ergopeptine and one of the ergot alkaloids. It is usually found in endophyte-infected species of grass like Tall fescue or Perennial Ryegrass. It is toxic to cattle feeding on infected grass, probably because is acts as a vasoconstrictor....
- IUPAC name: Ergotaman-3',6',18-trione, 12'-hydroxy-2'-methyl-5'-(1-methylethyl)-, (5'alpha)-
- CAS number: 2873-38-3

Name	R¹	R²	R³
Ergotamine		CH₃	benzyl Benzyl In organic chemistry, benzyl is the term used to describe the substituent or molecular fragment possessing the structure C6H5CH2-. Benzyl features a benzene ring attached to a CH2 group.-Nomenclature:...
Ergocristine Ergocristine Ergocristine is an ergopeptine and one of the ergot alkaloids.It was used as precursor in the manufacture of LSD as an alternative for the controlled substances ergotamine and ergometrine by various LSD manufacturers, including William Leonard Pickard...		CH(CH₃)₂	benzyl Benzyl In organic chemistry, benzyl is the term used to describe the substituent or molecular fragment possessing the structure C6H5CH2-. Benzyl features a benzene ring attached to a CH2 group.-Nomenclature:...
Ergocornine		CH(CH₃)₂	CH(CH₃)₂
Ergocryptine Ergocryptine Ergocryptine is an ergopeptine and one of the ergot alkaloids. It is often used to synthesis LSD, rather than ergotamine. It was the precursor being used by William Leonard Pickard in his clandestine LSD lab....		CH(CH₃)₂	CH₂CH(CH₃)₂
Bromocriptine Bromocriptine Bromocriptine , an ergoline derivative, is a dopamine agonist that is used in the treatment of pituitary tumors, Parkinson's disease , hyperprolactinaemia, neuroleptic malignant syndrome, and type 2 diabetes.- Indications :Amenorrhea, female infertility, galactorrhea, hypogonadism, and acromegaly...	Br Bromine Bromine ") is a chemical element with the symbol Br, an atomic number of 35, and an atomic mass of 79.904. It is in the halogen element group. The element was isolated independently by two chemists, Carl Jacob Löwig and Antoine Jerome Balard, in 1825–1826...	CH(CH₃)₂	CH₂CH(CH₃)₂
Ergovaline Ergovaline Ergovaline is an ergopeptine and one of the ergot alkaloids. It is usually found in endophyte-infected species of grass like Tall fescue or Perennial Ryegrass. It is toxic to cattle feeding on infected grass, probably because is acts as a vasoconstrictor....		CH₃	CH(CH₃)₂

Clavines
A variety of modifications to the basic ergoline are seen in nature, for example agroclavine

Agroclavine

Agroclavine belongs to the group of ergot alkaloids, such as ergotamine. Historically, the main use of argoclavine was to oxidize it to elymoclavine, which can then be used for ergot-based drug synthesis....

, elymoclavine, lysergol

Lysergol

Lysergol, is an alkaloid of the ergoline family that occurs as a minor constituent in some species of fungi , and in the morning glory family of plants , including the hallucinogenic seeds of Rivea corymbosa , Argyreia nervosa and Ipomoea violacea. Lysergol is not a controlled substance in the USA...

. Those deriving from dimethylergoline are referred to as clavines.

Others
Some synthetic ergoline derivatives do not fall easily into any of the above groups. Some examples are:

Pergolide
Pergolide
Pergolide is an ergoline-based dopamine receptor agonist used in some countries for the treatment of Parkinson's disease....

(INN
International Nonproprietary Name
An International Nonproprietary Name is the official nonproprietary or generic name given to a pharmaceutical substance, as designated by the World Health Organization...

)
- IUPAC name: (8beta)−8-((methylthio)methyl)−6-propyl-ergoline
- CAS number: 66104-22-1
Lisuride
Lisuride
Lisuride is an antiparkinson agent of the iso-ergoline class, chemically related to the dopaminergic ergoline Parkinson's drugs. Lisuride is described as free base and as hydrogen maleate salt.Lisuride is used to lower prolactin and, in low doses, to prevent migraine attacks...

(INN
International Nonproprietary Name
An International Nonproprietary Name is the official nonproprietary or generic name given to a pharmaceutical substance, as designated by the World Health Organization...

)
- IUPAC name: 3-(9,10-didehydro-6-methylergolin-8alpha-yl)−1,1-diethylurea
- CAS number: 18016-80-3

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