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Encyclopedia > Ergoline
Chemical structure of ergoline
Chemical structure of ergoline

Ergoline is a chemical compound whose structure serves as the skeleton for a diverse range of alkaloids and synthetic drugs. Substances derived from ergoline are used clinically as oxytocics and in the treatment of migraine and Parkinson's disease, and are implicated in the disease ergotism and in the action of psychedelic drugs such as ololiuhqui and LSD. Ergometrine and ergotamine are listed as Table I precursors under the United Nations Convention Against Illicit Traffic in Narcotic Drugs and Psychotropic Substances[1]. Image File history File links The chemical structure of ergoline selfmade by cacycle File history Legend: (cur) = this is the current file, (del) = delete this old version, (rev) = revert to this old version. ... A chemical substance is any material substance used in or obtained by a process in chemistry: A chemical compound is a substance consisting of two or more chemical elements that are chemically combined in fixed proportions. ... A compound is an area of land that is surrounded by fences, walls, or barbed wire and is used for a particular purpose, especially an area containing buildings and where the entry and exit of people is controlled. ... An alkaloid is a nitrogenous organic molecule that has a pharmacological effect on humans and other animals. ... Generally, synthetic means pertaining to synthesis, i. ... Many drugs are provided in tablet form. ... Ergotism is the effect of long-term ergot poisoning, classically due to the ingestion of the alkaloids produced by the Claviceps purpurea fungus which infects rye and other grains, and more recently by the action of a number of ergoline-based drugs. ... This entry pertains to the word psychedelic, its origin and uses. ... Many drugs are provided in tablet form. ... Binomial name Rivea corymbosa (L.)Hallier f. ... D-Lysergic Acid Diethylamide, commonly called acid, LSD, or LSD-25, is a powerful semisynthetic psychedelic drug. ... United Nations Convention Against Illicit Traffic in Narcotic Drugs and Psychotropic Substances Opened for signature December 20, 1988[1] at Vienna Entered into force November 11, 1990[2] Conditions for entry into force 20 ratifications Parties 170[3] The 1988 United Nations Convention Against Illicit Traffic in Narcotic Drugs and...

Contents


Chemistry

There are three main classes of ergoline derivatives, the water-soluble amides of lysergic acid, the water-insoluble ergopeptide alkaloids, and the clavine group. In chemistry, the term amide has several meanings. ... Peptides (from the Greek πεπτος, digestable), are the family of molecules formed from the linking, in a defined order, of various amino acids. ...


Lysergic acid amides

The prototype of this class is

  • Ergine (d-lysergic acid amide, LSA, LAA, LA-111)

Other important members include: Categories: Chemistry stubs | Alkaloids | Amines | Aromatic compounds | Hallucinogens | Heterocyclic bases ... IUPAC nomenclature is a systematic way of naming organic chemical compounds. ... CAS registry numbers are unique numerical identifiers for chemical compounds, polymers, biological sequences and alloys. ...

  • Ergonovine (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
  • Methergine (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
  • Methysergide (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
  • LSD (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. An International Nonproprietary Name (INN) is the official non-proprietary or generic name given to a pharmaceutical substance, as designated by the World Health Organization. ... IUPAC nomenclature is a systematic way of naming organic chemical compounds. ... CAS registry numbers are unique numerical identifiers for chemical compounds, polymers, biological sequences and alloys. ... An International Nonproprietary Name (INN) is the official non-proprietary or generic name given to a pharmaceutical substance, as designated by the World Health Organization. ... IUPAC nomenclature is a systematic way of naming organic chemical compounds. ... CAS registry numbers are unique numerical identifiers for chemical compounds, polymers, biological sequences and alloys. ... An International Nonproprietary Name (INN) is the official non-proprietary or generic name given to a pharmaceutical substance, as designated by the World Health Organization. ... IUPAC nomenclature is a systematic way of naming organic chemical compounds. ... CAS registry numbers are unique numerical identifiers for chemical compounds, polymers, biological sequences and alloys. ... D-Lysergic Acid Diethylamide, commonly called acid, LSD, or LSD-25, is a powerful semisynthetic psychedelic drug. ... An International Nonproprietary Name (INN) is the official non-proprietary or generic name given to a pharmaceutical substance, as designated by the World Health Organization. ... IUPAC nomenclature is a systematic way of naming organic chemical compounds. ... CAS registry numbers are unique numerical identifiers for chemical compounds, polymers, biological sequences and alloys. ... Many chemical compounds, especially hydrocarbons, can exist in different geometric configurations. ...

Name R1 N1 N2
ergine
ergonovine CH(CH3)CH2OH
methergine CH(CH2CH3)CH2OH
methysergide CH3 CH(CH2CH3)CH2OH
LSD CH2CH3 CH2CH3


Image File history File links PPCHTeX source: startchemical[size=big] chemical[SIX,B,EB246] chemical[SIX,MOV2,-SS3,B156,EB1,-SB4,Z4,SR4,RZ4][sf N,sf R1] chemical[SIX,MOV6,B,+RB1,+RZ1][sf H] chemical[SIX,MOV6,+SB1,-SB2,B3456,EB4,R2,-RD6,Z2,RZ2,-RZ6][sf N... In chemistry a methyl-group is a hydrophobic Alkyl functional group which is derived from methane (CH4). ... D-Lysergic Acid Diethylamide, commonly called acid, LSD, or LSD-25, is a powerful semisynthetic psychedelic drug. ... Ethyl is a two-carbon substituent in organic chemistry. ... Ethyl is a two-carbon substituent in organic chemistry. ...


Peptide alkaloids

These compounds have a tripeptide structure attached to the basic ergoline ring, in the same location as the amide group of the lysergic acid derivatives. Some of the important ergopeptides 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. Peptides (from the Greek πεπτος, digestable), are the family of molecules formed from the linking, in a defined order, of various amino acids. ... In chemistry, the term amide has several meanings. ...

  • Ergotamine
    • IUPAC name: Ergotaman-3',6',18-trione, 12'-hydroxy-2'-methyl-5'-(phenylmethyl)-, (5'-alpha)- (9CI)
    • CAS number: 113-15-5
  • Ergocristine
    • 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
    • IUPAC name:Ergotaman-3',6',18-trione, 12'-hydroxy-2'-(1-methylethyl)-5'-(2-methylpropyl)-, (5'alpha)- (9CI)
    • CAS number: 511-09-1
  • Bromocriptine (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
  • Ergovaline
    • IUPAC name: Ergotaman-3',6',18-trione, 12'-hydroxy-2'-methyl-5'-(1-methylethyl)-, (5'alpha)-
    • CAS number: 2873-38-3
Name R2 R2' R5'
ergotamine CH3 benzyl
ergocristine CH(CH3)2 benzyl
ergocornine CH(CH3)2 CH(CH3)2
ergocryptine CH(CH3)2 CH2CH(CH3)2
bromocriptine Br CH(CH3)2 CH2CH(CH3)2
ergovaline CH3 CH(CH3)2


IUPAC nomenclature is a systematic way of naming organic chemical compounds. ... CAS registry numbers are unique numerical identifiers for chemical compounds, polymers, biological sequences and alloys. ... IUPAC nomenclature is a systematic way of naming organic chemical compounds. ... CAS registry numbers are unique numerical identifiers for chemical compounds, polymers, biological sequences and alloys. ... IUPAC nomenclature is a systematic way of naming organic chemical compounds. ... CAS registry numbers are unique numerical identifiers for chemical compounds, polymers, biological sequences and alloys. ... IUPAC nomenclature is a systematic way of naming organic chemical compounds. ... CAS registry numbers are unique numerical identifiers for chemical compounds, polymers, biological sequences and alloys. ... An International Nonproprietary Name (INN) is the official non-proprietary or generic name given to a pharmaceutical substance, as designated by the World Health Organization. ... IUPAC nomenclature is a systematic way of naming organic chemical compounds. ... CAS registry numbers are unique numerical identifiers for chemical compounds, polymers, biological sequences and alloys. ... IUPAC nomenclature is a systematic way of naming organic chemical compounds. ... CAS registry numbers are unique numerical identifiers for chemical compounds, polymers, biological sequences and alloys. ... Image File history File links PPCHTeX source: startchemical[size=big] chemical[SIX,B,EB246] chemical[SIX,MOV2,-SS3,B156,EB1,-SB4,Z4,R2, SR4,RZ2,RZ4][sf N, sf R2, sf H] chemical[SIX,MOV6,B,+RB1,+RZ1][sf H] chemical[SIX,MOV6,+SB1,-SB2,B3456,EB4,R2,-RD6,Z2... In chemistry a methyl-group is a hydrophobic Alkyl functional group which is derived from methane (CH4). ... Benzyl is the Organic chemistry term for the radical C6H5CH2-. It is obtained by removing a proton from benzene. ... Benzyl is the Organic chemistry term for the radical C6H5CH2-. It is obtained by removing a proton from benzene. ... General Name, Symbol, Number bromine, Br, 35 Series halogens Group, Period, Block 17 (VIIA), 4, p Density, Hardness 3119 kg/m3 (300 K), NA Appearance Gas: red-brown solid: metallic luster Atomic properties Atomic weight 79. ... In chemistry a methyl-group is a hydrophobic Alkyl functional group which is derived from methane (CH4). ...


Clavines

A variety of modifications to the basic ergoline are seen in nature, for example agroclavine, elymoclavine, lysergol. Those deriving from dimethylergoline are referred to as clavines.


Others

Some synthetic ergoline derivatives do fall easily into any of the above groups. Some examples are:

An International Nonproprietary Name (INN) is the official non-proprietary or generic name given to a pharmaceutical substance, as designated by the World Health Organization. ... IUPAC nomenclature is a systematic way of naming organic chemical compounds. ... CAS registry numbers are unique numerical identifiers for chemical compounds, polymers, biological sequences and alloys. ... An International Nonproprietary Name (INN) is the official non-proprietary or generic name given to a pharmaceutical substance, as designated by the World Health Organization. ... IUPAC nomenclature is a systematic way of naming organic chemical compounds. ... CAS registry numbers are unique numerical identifiers for chemical compounds, polymers, biological sequences and alloys. ...

History & Uses

Ergoline alkaloids 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 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. An alkaloid is a nitrogenous organic molecule that has a pharmacological effect on humans and other animals. ... Ergot is the infection of grain with Claviceps purpurea fungus , the fungus itself, or the disease in humans and animals that eat the fungus. ... Ergotism is the effect of long-term ergot poisoning, classically due to the ingestion of the alkaloids produced by the Claviceps purpurea fungus which infects rye and other grains, and more recently by the action of a number of ergoline-based drugs. ... Chemistry (in Greek: χημεία) is the science of matter and its interactions with energy and itself (see physics, biology). ... 1907 was a common year starting on Tuesday (see link for calendar). ... For a list of biologically injurious substances, including toxins and other materials, as well as their effects, see poison. ... Therapy (in Greek: θεραπεία) or treatment is the attempted remediation of a health problem, usually following a diagnosis. ... 1918 was a common year starting on Tuesday (see link for calendar). ...


With the determination of the basic chemical structure of the ergot alkaloids in the early 1930s, an era of intensive exploration of synthetic derivatives began. In addition to the naturally occurring ergonovine (used as an oxytocic) and ergotamine (an analgesic used to control migraine), synthetic derivatives of continuing importance today are the oxytocic methergine, the anti-migraine drugs dihydroergotamine and methysergide, the anti-senility nootropic (smart drug) Hydergine™ (a mixture of dihydroergotoxine mesylates, INN: ergoline mesylates), and bromocriptine, used for numerous purposes including treatment of Parkinson's disease. Newer synthetic ergolines used for Parkinson's disease include pergolide and lisuride. Perhaps the most famous ergoline derivative of all is the psychedelic drug LSD. Chemical structure is the arrangement of atoms within a molecule, usually linked by covalent bonds. ... Generally, synthetic means pertaining to synthesis, i. ... An analgesic (colloquially known as painkiller) is any member of the diverse group of drugs used to relieve pain. ... Nootropics are so-called smart drugs. ... An International Nonproprietary Name (INN) is the official non-proprietary or generic name given to a pharmaceutical substance, as designated by the World Health Organization. ... This entry pertains to the word psychedelic, its origin and uses. ... A drug is any substance that can be used to modify a chemical process or processes in the body, for example to treat an illness, relieve a symptom, enhance a performance or ability, or to alter states of mind. ... D-Lysergic Acid Diethylamide, commonly called acid, LSD, or LSD-25, is a powerful semisynthetic psychedelic drug. ...


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 plants. 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 Hawaiian 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 hallucinogenic effects. 1960 was a leap year starting on Friday (link will take you to calendar). ... Dr. Albert Hofmann Dr. Albert Hofmann (born 11 January 1906) is a prominent Swiss scientist and best known as the father of LSD. He was born in Baden, Switzerland, and studied chemistry at the University of Zurich. ... Divisions Chytridiomycota Zygomycota Ascomycota Basidiomycota The Fungi (singular: fungus) are a large group of organisms ranked as a kingdom within the Domain Eukaryota. ... Classes Magnoliopsida - Dicots Liliopsida - Monocots The flowering plants (also angiosperms or Magnoliophyta) are one of the major groups of modern plants, comprising those that produce seeds in specialized reproductive organs called flowers, where the ovulary or carpel is enclosed. ... Binomial name Rivea corymbosa (L.)Hallier f. ... Binomial nomenclature Ipomoea violacea L. Ipomoea violacea is a species of morning glory that occurs throughout the tropics. ... Genera See text The Convolvulaceae, the bindweed or morning glory family, is a group of about 60 genera and more than 1,650 species of mostly herbaceous vines, but also trees, shrubs and herbs. ... Binomial name Rivea corymbosa (L.)Hallier f. ... Binomial nomenclature Ipomoea violacea L. Ipomoea violacea is a species of morning glory that occurs throughout the tropics. ... Optical isomerism is a form of isomerism (specifically stereoisomerism) whereby the different 2 isomers are the same in every way except being non-superimposable mirror images* of each other. ... State nickname: The Aloha State Other U.S. States Capital Honolulu Largest city Honolulu Governor Linda Lingle Official languages Hawaiian and English Area 28,337 km² (43rd)  - Land 16,649 km²  - Water 11,672 km² (41. ... Binomial name Argyreia nervosa (Burm. ... Categories: Chemistry stubs | Alkaloids | Amines | Aromatic compounds | Hallucinogens | Heterocyclic bases ... Hallucinogenic drug - drugs that can alter sensory perceptions. ...


See Also

Ergotism is the effect of long-term ergot poisoning, classically due to the ingestion of the alkaloids produced by the Claviceps purpurea fungus which infects rye and other grains, and more recently by the action of a number of ergoline-based drugs. ... Ergot is the infection of grain with Claviceps purpurea fungus , the fungus itself, or the disease in humans and animals that eat the fungus. ... D-Lysergic Acid Diethylamide, commonly called acid, LSD, or LSD-25, is a powerful semisynthetic psychedelic drug. ... Categories: Chemistry stubs | Alkaloids | Amines | Aromatic compounds | Hallucinogens | Heterocyclic bases ... Dr. Albert Hofmann Dr. Albert Hofmann (born 11 January 1906) is a prominent Swiss scientist and best known as the father of LSD. He was born in Baden, Switzerland, and studied chemistry at the University of Zurich. ...

External Links

Hallucinogenic lysergamides edit

{LSD} {Ergine} {Ergoline} {Ergonovine} Hallucinogenic drugs or hallucinogens are drugs that can alter sensory perceptions, elicit alternate states of consciousness, or cause hallucinations. ... D-Lysergic Acid Diethylamide, commonly called acid, LSD, or LSD-25, is a powerful semisynthetic psychedelic drug. ... Categories: Chemistry stubs | Alkaloids | Amines | Aromatic compounds | Hallucinogens | Heterocyclic bases ... Ergonovine, or ergometrine, or d-lysergic acid beta-propanolamide, is one of primary ergot alkaloids and an alkaloid of many species of morning glory, too. ...


  Results from FactBites:
 
Reference.com/Encyclopedia/Ergoline (717 words)
Ergoline is a chemical compound whose structural skeleton is contained in a diverse range of alkaloids and a few psychedelic drugs (ololiuhqui, LSD).
Ergoline derivitives are used clinically for the purpose of vasoconstriction (5-HT 1 Agonists - Ergotamine) and in the treatment of migraine (used with caffeine) and Parkinson's disease, some are implicated in the disease ergotism.
Ergoline alkaloids were first isolated from ergot, a fungus that infects grain and causes the disease ergotism.
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