Structure via PubChem · Public domain (PubChem)
ergoline
Sign in to saveAlso known as (6aR,10aR)-4,6,6a,7,8,9,10,10a-octahydroindolo[4,3-fg]quinoline
Ergoline is a core structure in many alkaloids and their synthetic derivatives. Ergoline alkaloids were first characterized in ergot. Some of these are implicated in the condition of 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.
Key facts
- Drug.Watchedfields
- changed
- Drug.verifiedrevid
- 446242223
- Drug.image
- Ergoline Structural Formulae V.1.svg
- Drug.image_class
- skin-invert-image
- Drug.width
- 135px
- Drug.image2
- Ergoline 3D.png
- Drug.image_class2
- bg-transparent
- Drug.width2
- 200px
- Drug.ATC_prefix
- None
- Drug.CAS_number
- 478-88-6
- Drug.UNII
- D5RC6H62GW
- Drug.PubChem
- 6857537
- Drug.ChemSpiderID
- 5256873
- Drug.ChEBI
- 38484
- Drug.IUPAC_name
- (6aR)-4,6,6a,7,8,9,10,10a-Octahydroindolo[4,3-fg]quinoline
- Drug.C
- 14
- Drug.H
- 16
- Drug.N
- 2
via Wikipedia infobox
Chemical data
- Formula
- C14H16N2
- Molecular weight
- 212.29 g/mol
- IUPAC name
- (6aR,10aR)-4,6,6a,7,8,9,10,10a-octahydroindolo[4,3-fg]quinoline
- SMILES
- C1C[C@H]2[C@@H](CC3=CNC4=CC=CC2=C34)NC1
- InChIKey
- RHGUXDUPXYFCTE-ZWNOBZJWSA-N
- XLogP
- 2.3
- Polar surface area
- 27.8 Ų
- H-bond donors
- 2
- H-bond acceptors
- 1
- Formal charge
- 0
via PubChem
Wikidata facts
- Mass
- 212.131349
Show 4 more facts
- chemical formula
- C₁₄H₁₆N₂
- Commons category
- Ergoline
- isomeric SMILES
- C1C[C@H]2[C@@H](CC3=CNC4=CC=CC2=C34)NC1
- canonical SMILES
- C1CC2C(CC3=CNC4=CC=CC2=C34)NC1
Sources (2)
via Wikidata · CC0
~13 min read
Article
13 sectionsContents
- Natural occurrence
- History
- Uses
- Mechanism of action
- Dopaminergic/antidopaminergic
- Serotonergic/antiserotonergic
- Ergoline derivatives
- Lysergic acid amides
- Clavines
- Others
- See also
- References
- External links
Ergoline is a core structure in many alkaloids and their synthetic derivatives. Ergoline alkaloids were first characterized in ergot. Some of these are implicated in the condition of 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.
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.