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Setoclavine

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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-hexahydroindoloquinolin-9-ol
Identifiers
CAS Number	519-12-0
3D model (JSmol)	Interactive image
ChemSpider	9657036
PubChem CID	11482216
UNII	UE9HT9P885
CompTox Dashboard (EPA)	DTXSID301256140
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/s1Key: BGVUWLLRNRBDAY-ZBFHGGJFSA-N
SMILES O3(/C=C2/c4cccc1c4c(c1)C2N(C3)C)C
Properties
Chemical formula	C₁₆H₁₈N₂O
Molar mass	254.333 g·mol
Appearance	prisms
Melting point	229 to 234 °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 , 100 kPa). Infobox references

Chemical compound

Setoclavine is an ergot alkaloid.

References

J. E. Saxton (1960). "The Indole Alkaloids". In The Alkaloids, Vol. VII, (R. H. F. Manske, Ed.), pp. 4-183, New York: Academic Press.
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.

v t e Ergolines
Lysergic acid derivatives	2-Bromo-LSD (BOL-148) Amesergide Bromerguride (2-bromolisuride) Bromocriptine Cabergoline Dihydroergocornine Dihydroergocristine Dihydroergocryptine Dihydroergometrine (Dihydroergonovine, Dihydroergobasine) Dihydroergosine Dihydroergotamine Epicriptine Ergine (LSA; LA-111; Lysergamide) Ergocornine Ergocristine Ergocryptine Ergoloid (Dihydroergotoxine) Ergometrine (Ergonovine, Ergobasine) Ergometrinine Ergostine Ergotamine Ergotoxine Ergovaline Fludihydroergotamine Lisuride LY-215,840 LSH Lysergic acid Lysergic acid methyl ester Lysergine Lysergol Mergocriptine Mesulergine Metergoline Metergotamine MIPLA Methysergide Propisergide Sergolexole
Psychedelic lysergamides	1B-LSD 1cP-LSD 1P-ETH-LAD 1P-LSD AL-LAD ALD-52 BU-LAD CYP-LAD Diallyllysergamide (DAL) Dimethyllysergamide (DAM-57) ECPLA Ergonovine ETFELA ETH-LAD IP-LAD LAMPA LAE-32 LSD (lysergide) LPD-824 LSM-775 LSH LSD-Pip Lysergic Acid 2-Butylamide Lysergic Acid 2,4-Dimethylazetidide Lysergic Acid 3-Pentylamide Lysergic acid cyclobutylamide Lysergic acid cyclopentylamide Methylergometrine (Methylergonovine, Methylergobasine) MIPLA MLD-41 PARGY-LAD PRO-LAD
Clavines	9-Deacetoxyfumigaclavine C Agroclavine Chanoclavine Chanoclavine II Costaclavin Cycloclavine Elymoclavine Epoxyagroclavine Festuclavine Fumigaclavine A Fumigaclavine B Fumigaclavine C Paliclavine Penniclavine Setoclavine
Other ergolines	Acetergamine Brazergoline Cianergoline CY-208,243 Delergotrile Descarboxylysergic acid Disulergine Dosergoside Ergoline Etisulergine Lergotrile Nicergoline Pergolide Proterguride Romergoline Terguride Tiomergine Voxergolide
Related compounds	Adrogolide Naxagolide Quinagolide
Natural sources	Achnatherum robustum (Sleepy Grass) Claviceps spp. (Ergot) Morning glory: Argyreia nervosa (Hawaiian Baby Woodrose), Ipomoea spp.(Morning Glory, Tlitliltzin, Badoh Negro), Rivea corymbosa (Coaxihuitl, Ololiúqui)

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