Setoclavine

Setoclavine
Names
IUPAC name
6,8β-Dimethyl-9,10-didehydroergolin-8α-ol
Systematic IUPAC name
(6aR,9S)-7,9-Dimethyl-4,6,6a,7,8,9-hexahydroindolo[4,3-fg]quinolin-9-ol
Identifiers
CAS Number
  • 519-12-0 checkY
3D model (JSmol)
  • Interactive image
ChemSpider
  • 9657036
PubChem CID
  • 11482216
UNII
  • UE9HT9P885 checkY
CompTox Dashboard (EPA)
  • DTXSID301256140 Edit this at Wikidata
InChI
  • InChI=1S/C16H18N2O/c1-16(19)7-12-11-4-3-5-13-15(11)10(8-17-13)6-14(12)18(2)9-16/h3-5,7-8,14,17,19H,6,9H2,1-2H3/t14-,16+/m1/s1
    Key: BGVUWLLRNRBDAY-ZBFHGGJFSA-N
  • O[C@]3(/C=C2/c4cccc1c4c(c[nH]1)C[C@H]2N(C3)C)C
Properties
Chemical formula
 C16H18N2O
Molar mass 254.333 g·mol−1
Appearance prisms
Melting point 229 to 234[1] °C (444 to 453 °F; 502 to 507 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references
Chemical compound

Setoclavine is an ergot alkaloid.[2]

References

  1. ^ J. E. Saxton (1960). "The Indole Alkaloids". In The Alkaloids, Vol. VII, (R. H. F. Manske, Ed.), pp. 4-183, New York: Academic Press.
  2. ^ Liras, S; Lynch, CL; Fryer, AM; Vu, BT; Martin, SF (2001). "Applications of vinylogous Mannich reactions. Total syntheses of the Ergot alkaloids rugulovasines a and B and setoclavine". Journal of the American Chemical Society. 123 (25): 5918–24. doi:10.1021/ja010577w. PMID 11414824.


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Ergolines
Lysergic acid
derivatives
Psychedelic
lysergamidesClavinesOther
ergolinesNatural
sources

Morning glory: Argyreia nervosa (Hawaiian Baby Woodrose), Ipomoea spp.(Morning Glory, Tlitliltzin, Badoh Negro), Rivea corymbosa (Coaxihuitl, Ololiúqui)


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