Agroclavine

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
CAS Number	548-42-5^Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:2519^N
ChEMBL	ChEMBL449081^Y
ChemSpider	66176^Y
ECHA InfoCard	100.008.135
PubChem CID	73484
UNII	A8SW57GO7T^Y
CompTox Dashboard (EPA)	DTXSID10970144
InChI 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^Y Key: XJOOMMHNYOJWCZ-UKRRQHHQSA-N^Y 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
SMILES c2c3c1c(cccc1[nH]2)[C@H]4\C=C(/CN([C@@H]4C3)C)C
Properties
Chemical formula	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). N verify (what is ^YN ?) Infobox references

Agroclavine belongs to the group of ergot alkaloids, which also includes ergotamine.^[1] Historically, the main use of agroclavine was in the synthesis of ergot-based drugs; agroclavine can be oxidized to elymoclavine, which then undergoes further processing.^[2]

References

^ 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. doi:10.1039/jr9620000421.
^ Cordell GA (2002). The Alkaloids: Chemistry and Biology. Gulf Professional Publishing. pp. 6–. ISBN 978-0-12-469558-0.

v t e Alkaloid groups
Indole	5-MeO-DMT Alstonine Dimethyltryptamine Harmala alkaloids Geissolosimine Psilocin Psilocybin Reserpine Serotonin Tryptamine Yohimbine
Phenethylamine	Amphetamine Cathinone Dopamine Ephedrine Mescaline Methamphetamine Phenethylamine Tyramine
Purine	Caffeine Theobromine Theophylline
Pyridine	Coniine
Pyrrolidine	Nicotine
Quinoline	Quinine
Isoquinoline	Codeine Morphine
Tropane	Atropine Cocaine Hyoscyamine Scopolamine
Terpenoid	Aconitine Solanine
Betaines	Choline Muscarine

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 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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