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Epoxyagroclavine

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Ergot alkaloid

Epoxyagroclavine
Names

IUPAC name 6,8β-Dimethyl-8α,9α-epoxy-10β-ergoline
Systematic IUPAC name (1aR,3aR,9bS,9cS)-1a,3-Dimethyl-1a,2,3,3a,4,6,9b,9c-octahydroindolooxirenoquinoline
Identifiers
CAS Number	82564-34-9
3D model (JSmol)	Interactive image
ChemSpider	118111
PubChem CID	133945
CompTox Dashboard (EPA)	DTXSID101002787
InChI InChI=1S/C16H18N2O/c1-16-8-18(2)12-6-9-7-17-11-5-3-4-10(13(9)11)14(12)15(16)19-16/h3-5,7,12,14-15,17H,6,8H2,1-2H3/t12-,14+,15+,16-/m1/s1Key: WASFVUNJIDBCHV-SYAUCNOPSA-N
SMILES C12CN(3Cc4cc5c4c(ccc5)31O2)C
Properties
Chemical formula	C₁₆H₁₈N₂O
Molar mass	254.327
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Infobox references

Chemical compound

Epoxyagroclavine is an ergot alkaloid made by permafrost Penicillium.

References

Kozlovskiĭ, AG; Zhelifonova, VP; Adanin, VM; Antipova, TV; Ozerskaia, SM; Kochkina, GA; Grafe, U (2003). "". Mikrobiologiia. 72 (6): 816–21. PMID 14768549.

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)

Category:

Ergot alkaloids

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