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Agroclavine

From Wikipedia, the free encyclopedia

Agroclavine
Names
IUPAC name
6,8-Dimethyl-8,9-didehydroergoline
Systematic IUPAC name
(6aR,10aR)-7,9-Dimethyl-4,6,6a,7,8,10a-hexahydroindolo[4,3-fg]quinoline
Other names
8,9-Didehydro-6,8-dimethylergoline
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard100.008.135Edit this at Wikidata
UNII
  • InChI=1S/C16H18N2/c1-10-6-13-12-4-3-5-14-16(12)11(8-17-14)7-15(13)18(2)9-10/h3-6,8,13,15,17H,7,9H2,1-2H3/t13-,15-/m1/s1 checkY
    Key: XJOOMMHNYOJWCZ-UKRRQHHQSA-N checkY
  • InChI=1S/C16H18N2/c1-10-6-13-12-4-3-5-14-16(12)11(8-17-14)7-15(13)18(2)9-10/h3-6,8,13,15,17H,7,9H2,1-2H3/t13-,15-/m1/s1
  • c2c3c1c(cccc1[nH]2)[C@H]4\C=C(/CN([C@@H]4C3)C)C
Properties
C16H18N2
Molar mass238.334 g·mol−1
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)
Chemical compound

Agroclavine belongs to the group ofergot alkaloids, which also includesergotamine.[1] Historically, the main use of agroclavine was in the synthesis of ergot-based drugs; agroclavine can be oxidized toelymoclavine, which then undergoes further processing.[2]

References

[edit]
  1. ^Bhattacharji, S., Birch, A. J., Brack, A., Hofmann, A., Kobel, H., Smith, D. C. C., Smith, Herchel, Winter J. (1962). "Biosynthesis. XXVII. The biosynthesis of ergot alkaloids".Journal of the Chemical Society:421–425.doi:10.1039/jr9620000421.
  2. ^Cordell GA (2002).The Alkaloids: Chemistry and Biology. Gulf Professional Publishing. pp. 6–.ISBN 978-0-12-469558-0.
Alkaloid groups
Indole
Phenethylamine
Purine
Pyridine
Pyrrolidine
Quinoline
Isoquinoline
Tropane
Terpenoid
Betaines
Ergolines
(incl.lysergines)
Clavines
(6,8-dimethylergolines)
Lysergamides
(lysergic acid amides)
Ergopeptines
(peptide ergolines)
Partial ergolines
Related compounds
Natural sources
Retrieved from "https://en.wikipedia.org/w/index.php?title=Agroclavine&oldid=1197157460"
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