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Ergoline information


Ergoline
Clinical data
ATC code
  • none
Identifiers
IUPAC name
  • (6aR)-4,6,6a,7,8,9,10,10a-Octahydroindolo[4,3-fg]quinoline
CAS Number
  • 478-88-6 checkY
PubChem CID
  • 6857537
ChemSpider
  • 5256873 checkY
UNII
  • D5RC6H62GW
ChEBI
  • CHEBI:38484 checkY
CompTox Dashboard (EPA)
  • DTXSID00963944 Edit this at Wikidata
Chemical and physical data
FormulaC14H16N2
Molar mass212.296 g·mol−1
3D model (JSmol)
  • Interactive image
SMILES
  • [H][C@@]34Cc1c[nH]c2cccc(c12)[C@@]3([H])CCCN4
InChI
  • InChI=1S/C14H16N2/c1-3-11-10-4-2-6-15-13(10)7-9-8-16-12(5-1)14(9)11/h1,3,5,8,10,13,15-16H,2,4,6-7H2/t10-,13-/m1/s1 checkY
  • Key:RHGUXDUPXYFCTE-ZWNOBZJWSA-N checkY
  (verify)

Ergoline is a chemical compound whose structural skeleton is contained in a variety of alkaloids, referred to as ergoline derivatives or ergoline alkaloids. Ergoline alkaloids, one being ergine, were initially characterized in ergot. Some of these are implicated in the condition ergotism, which can take a convulsive form or a gangrenous form. Even so, many ergoline alkaloids have been found to be clinically useful. Annual world production of ergot alkaloids has been estimated at 5,000–8,000 kg of all ergopeptines and 10,000–15,000 kg of lysergic acid, used primarily in the manufacture of semi-synthetic derivatives.[1]

Others, such as lysergic acid diethylamide, better known as LSD, a semi-synthetic derivative, and ergine, a natural derivative found in Argyreia nervosa, Ipomoea tricolor and related species, are known psychedelic substances.[2]

  1. ^ Schiff PL (October 2006). "Ergot and its alkaloids". American Journal of Pharmaceutical Education. 70 (5): 98. doi:10.5688/aj700598. PMC 1637017. PMID 17149427.
  2. ^ Juszczak GR, Swiergiel AH (2013). "Recreational use of D-lysergamide from the seeds of Argyreia nervosa, Ipomoea tricolor, Ipomoea violacea, and Ipomoea purpurea in Poland". Journal of Psychoactive Drugs. 45 (1): 79–93. doi:10.1080/02791072.2013.763570. PMID 23662334. S2CID 22086799.

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Ergoline

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Ergoline is a chemical compound whose structural skeleton is contained in a variety of alkaloids, referred to as ergoline derivatives or ergoline alkaloids...

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Dopamine agonist

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agonists have two subclasses: ergoline and non-ergoline agonists. Both subclasses target dopamine D2-type receptors. Types of ergoline agonists are cabergoline...

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Ergine

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Ergine, also known as d-lysergic acid amide (LSA) and d-lysergamide, is an ergoline alkaloid that occurs in various species of vines of the Convolvulaceae...

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Argyreia nervosa

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medicine for their medicinal value. Argyreia nervosa seeds contain various ergoline alkaloids such as ergine. A study reported stereoisomers of ergine to be...

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Ergotamine

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of alkaloids; it is structurally and biochemically closely related to ergoline. It is structurally similar to several neurotransmitters, and it acts as...

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Convolvulaceae

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exploited for their medicinal value as purgatives. Some species contain ergoline alkaloids that are likely responsible for the use of these species as ingredients...

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Methylergometrine

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methylergonovine and sold under the brand name Methergine, is a medication of the ergoline and lysergamide groups which is used as an oxytocic in obstetrics and in...

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Bromocriptine

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originally marketed as Parlodel and subsequently under many brand names, is an ergoline derivative and dopamine agonist that is used in the treatment of pituitary...

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Ergotism

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rye and other cereals, and more recently by the action of a number of ergoline-based drugs. It is also known as ergotoxicosis, ergot poisoning, and Saint...

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Lysergic acid

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D-lysergic acid and (+)-lysergic acid, is a precursor for a wide range of ergoline alkaloids that are produced by the ergot fungus and found in the seeds...

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Rye

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from eating rye and other grains infected by ergot fungi (which produce ergoline toxins in infected products). Although it is no longer a common illness...

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Lisuride

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brand name Dopergin among others, is a monoaminergic medication of the ergoline class which is used in the treatment of Parkinson's disease, migraine,...

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Claviceps purpurea

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connected via amide linkage to a lysergic acid (ergoline) moiety, and other alkaloids of the ergoline group that are biosynthesized by the fungus. Ergot...

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MDMA

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BMY-14802 Cannabidiol Dimemebfe Dopamine Ebalzotan Eltoprazine Enciprazine Ergolines (e.g., bromocriptine, cabergoline, dihydroergotamine, ergotamine, lisuride...

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Morning glory

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for the edible tuber. The seeds of many species of morning glory contain ergoline alkaloids such as the psychedelic ergonovine and ergine (LSA). Seeds of...

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Ergot

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connected via amide linkage to a lysergic acid (ergoline) moiety, and other alkaloids of the ergoline group that are biosynthesized by the fungus. Ergot...

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Risperidone

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labetalol) Buflomedil Bunazosin Corynanthine Dapiprazole Domesticine Doxazosin Ergolines (e.g., acetergamine, ergotamine, dihydroergotamine, lisuride, nicergoline...

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Ketamine

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SKF-38,393 SKF-77,434 SKF-81,297 SKF-82,958 SKF-83,959 Trepipam Zelandopam Ergolines: Cabergoline CY-208,243 Dihydroergocryptine LEK-8829 Lisuride Pergolide...

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LSD

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naturally occurring amino acid L-tryptophan, the precursor to all biosynthetic ergoline compounds. However, LSD and iso-LSD, the two C-8 isomers, rapidly interconvert...

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Rotigotine

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under the brand name Neupro among others, is a dopamine agonist of the non-ergoline class of medications indicated for the treatment of Parkinson's disease...

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Pergolide

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under the brand name Permax and Prascend (veterinary) among others, is an ergoline-based dopamine receptor agonist used in some countries for the treatment...

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Rilmenidine

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labetalol) Buflomedil Bunazosin Corynanthine Dapiprazole Domesticine Doxazosin Ergolines (e.g., acetergamine, ergotamine, dihydroergotamine, lisuride, nicergoline...

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Indole alkaloid

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Convolvulaceae, in particular Ipomoea violacea and Turbina corymbosa, contain ergolines and lysergamides. Despite the considerable structural diversity, most...

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Lysergamides

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similar, often psychedelic, effects to those of the true tryptamines. Ergoline Bromocriptine Fumigaclavine C Hydergine Lisuride Pergolide Hofmann A (June...

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Salvia divinorum

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SKF-38,393 SKF-77,434 SKF-81,297 SKF-82,958 SKF-83,959 Trepipam Zelandopam Ergolines: Cabergoline CY-208,243 Dihydroergocryptine LEK-8829 Lisuride Pergolide...

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Ipomoea corymbosa

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1960 in a paper by Albert Hofmann. The seeds contain ergine (LSA), an ergoline alkaloid which is also present in ergot of rye and is similar in structure...

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Mirtazapine

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labetalol) Buflomedil Bunazosin Corynanthine Dapiprazole Domesticine Doxazosin Ergolines (e.g., acetergamine, ergotamine, dihydroergotamine, lisuride, nicergoline...

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Nicergoline

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in other areas of the body, particularly the lungs. Unlike many other ergolines, such as ergotamine, nicergoline is not associated with cardiac fibrosis...

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