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Ergovalide

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Ergovalide
Clinical data
Other namesLysergylvaline amide; N-Lysergylvalylamide; N-((1S)-1-(aminocarbonyl)-2-methylpropyl)-9,10-didehydro-6-methylergoline-8β-carboxamide
ATC code
  • None
Identifiers
  • (6aR,9R)-N-[(2S)-1-amino-3-methyl-1-oxobutan-2-yl]-7-methyl-6,6a,8,9-tetrahydro-4H-indolo[4,3-fg]quinoline-9-carboxamide
CAS Number
PubChem CID
ChemSpider
UNII
Chemical and physical data
FormulaC21H26N4O2
Molar mass366.465 g·mol−1
3D model (JSmol)
  • CC(C)[C@@H](C(=O)N)NC(=O)[C@H]1CN([C@@H]2CC3=CNC4=CC=CC(=C34)C2=C1)C
  • InChI=1S/C21H26N4O2/c1-11(2)19(20(22)26)24-21(27)13-7-15-14-5-4-6-16-18(14)12(9-23-16)8-17(15)25(3)10-13/h4-7,9,11,13,17,19,23H,8,10H2,1-3H3,(H2,22,26)(H,24,27)/t13-,17-,19+/m1/s1
  • Key:MOJONCDRJGJHBT-XVSDVWIESA-N

Ergovalide, also known as lysergylvaline amide or as N-lysergylvalylamide, is an ergot alkaloid of the lysergamide family found in Claviceps purpurea (ergot).[1][2] It is said to constitute about 10 to 20% of the alkaloid content of ergot.[2] However, according to a secondary source, ergovalide is probably a chemical artifact arising from solvolytic cleavage of ergocristine (lysergylvalylphenylalanylproline) (which is a highly variable constituent but can constitute as much as 50% of alkaloids in ergot).[1][3] Ergovalide was first described in the scientific literature by A. N. Ban'kovskaya and colleagues in 1973.[1][2]

See also

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References

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  1. ^ a b c Southon IW, Buckingham J (15 January 1989). Dictionary of Alkaloids, Second Edition with CD-ROM. CRC Press. ISBN 978-0-412-24910-5. Retrieved 6 May 2026.
  2. ^ a b c Ban'kovskaya AN, Sheichenko VI, Ban'kovskii AI, Vechkanova LD, Kabanov VS (1973). "Ergovalide — A new alkaloid from ergot". Chemistry of Natural Compounds. 9 (1): 139–140. Bibcode:1973CNatC...9..139B. doi:10.1007/BF00580933. ISSN 0009-3130.
  3. ^ Grusie T, Cowan V, Singh J, McKinnon J, Blakley B (25 April 2018). "Proportions of predominant Ergot alkaloids (Claviceps purpurea) detected in Western Canadian grains from 2014 to 2016". World Mycotoxin Journal. 11 (2): 259–264. doi:10.3920/WMJ2017.2241. ISSN 1875-0710. Ergocristine was the predominant alkaloid accounting for half of the total alkaloids in all grain types. This study documented that barley, rye, triticale and wheat collected across Western Canada had similar percentages of ergocornine (6±1%, P=0.201), ergocristine (48±2%, P=0.939), ergocryptine (17±2%, P=0.302) and ergosine (5±0.5%, P=0.239).