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Agroclavine

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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 InfoCard 100.008.135 Edit 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 mass 238.334 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Agroclavine belongs to the group of ergot alkaloids, such as ergotamine.[1] Historically, the main use of agroclavine was to oxidize it to elymoclavine, which can then be used for ergot-based drug synthesis.[2]

References

  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.
  2. ^ Cordell GA (2002). The Alkaloids: Chemistry and Biology. Gulf Professional Publishing. pp. 6–. ISBN 978-0-12-469558-0.
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