{"ATC Code":"N - Nervous system","Abbreviation":[],"Aliases":["Ergotamin","Ergonsvine","Ergotamina","ergotaminum","12'-Hydroxy-2'-methyl-5'α-(phenylmethyl)ergotaman-3',6',18-trione","(5'α)-12'-Hydroxy-2'-methyl-5'-(phenylmethyl)ergotoman-3',6',18-trione","Ergotaman-3',6',18-trione, 12'-hydroxy-2'-methyl-5'-(phenylmethyl)-, (5'-α)-","Ergo Kranit","Mono, Ergodryl","(4R,7R)-N-[(1S,2S,4R,7S)-7-benzyl-2-hydroxy-4-methyl-5,8-dioxo-3-oxa-6,9-diazatricyclo[7.3.0.0^{2,6}]dodecan-4-yl]-6-methyl-6,11-diazatetracyclo[7.6.1.0^{2,7}.0^{12,16}]hexadeca-1(16),2,9,12,14-pentaene-4-carboxamide","(4R,7R)-N-((1S,2S,4R,7S)-7-benzyl-2-hydroxy-4-methyl-5,8-dioxo-3-oxa-6,9-diazatricyclo(7.3.0.0^(2,6))dodecan-4-yl)-6-methyl-6,11-diazatetracyclo(7.6.1.0^(2,7).0^(12,16))hexadeca-1(16),2,9,12,14-pentaene-4-carboxamide","(6aR,9R)-N-((1S,2S,4R,7S)-7-benzyl-2-hydroxy-4-methyl-5,8-dioxo-3-oxa-6,9-diazatricyclo(7.3.0.02,6)dodecan-4-yl)-7-methyl-6,6a,8,9-tetrahydro-4H-indolo(4,3-fg)quinoline-9-carboxamide","N02CA02","(4R,7R)-N-((1S,2S,4R,7S)-7-benzyl-2-hydroxy-4-methyl-5,8-dioxo-3-oxa-6,9-diazatricyclo(7.3.0.02,6)dodecan-4-yl)-6-methyl-6,11-diazatetracyclo(7.6.1.02,7.012,16)hexadeca-1(16),2,9,12,14-pentaene-4-carboxamide","204-023-9","Gynergen","Ergomar","C33H35N5O5","ERM","Ergotamin; ergotaminum","GTPL149","Ergotamine tartrate, Avetol, Cornutamin, Ergam, Ergotartrate","HMS2089H22","Ergotamine dried down 100 microg/mL","DB00696"],"Biological Half-Life":"2 hours","CAS":"113-15-5","ChEBI":"CHEBI:64318","ChEMBL":"CHEMBL442","ChemicalClasses":[],"Chirality":"achiral","Color/Form":"Needles from alcohol; prisms from benzene; plates from acetone","Decomposition":"Decomposition at 212-214 °C.","Drug Classes":"Breast Feeding; Lactation; Milk, Human; Adrenergic Alpha-Agonists; Analgesics, Non-Narcotic; Ergot Alkaloids; Vasoconstrictor Agents","Drug Indication":"For use as therapy to abort or prevent vascular headache, e.g., migraine, migraine variants, or so called \"histaminic cephalalgia\".","Drug Warnings":"/BOXED WARNING/ Serious and/or life-threatening peripheral ischemia has been associated with the coadministration of ergotamine tartrate with potent CYP 3A4 inhibitors including protease inhibitors and macrolide antibiotics. Because CYP 3A4 inhibition elevates the serum levels of ergotamine tartrate, the risk for vasospasm leading to cerebral ischemia and/or ischemia of the extremities is increased. Hence, concomitant use of these medications is contraindicated.","EINECS":"204-023-9","Erowid Experience Reports":[],"Esters":[],"European Community (EC) Number":"204-023-9","FDA Pharmacological Classification":"PR834Q503T","Formating":[],"HMDB ID":"HMDB0014834","HeavyAtomCount":43,"Human Drugs":"Breast Feeding; Lactation; Milk, Human; Adrenergic Alpha-Agonists; Analgesics, Non-Narcotic; Ergot Alkaloids; Vasoconstrictor Agents","IUPACName":"(6aR,9R)-N-[(1S,2S,4R,7S)-7-benzyl-2-hydroxy-4-methyl-5,8-dioxo-3-oxa-6,9-diazatricyclo[7.3.0.02,6]dodecan-4-yl]-7-methyl-6,6a,8,9-tetrahydro-4H-indolo[4,3-fg]quinoline-9-carboxamide","InChI":"InChI=1S/C33H35N5O5/c1-32(35-29(39)21-15-23-22-10-6-11-24-28(22)20(17-34-24)16-25(23)36(2)18-21)31(41)38-26(14-19-8-4-3-5-9-19)30(40)37-13-7-12-27(37)33(38,42)43-32/h3-6,8-11,15,17,21,25-27,34,42H,7,12-14,16,18H2,1-2H3,(H,35,39)/t21-,25-,26+,27+,32-,33+/m1/s1","InChIKey":"XCGSFFUVFURLIX-VFGNJEKYSA-N","MeSH Pharmacological Classification":"A subclass of analgesic agents that typically do not bind to OPIOID RECEPTORS and are not addictive. Many non-narcotic analgesics are offered as NONPRESCRIPTION DRUGS. (See all compounds classified as Analgesics, Non-Narcotic.)","Melting Point":"213 °C","MolecularFormula":"C\u003csub\u003e33\u003c/sub\u003eH\u003csub\u003e35\u003c/sub\u003eN\u003csub\u003e5\u003c/sub\u003eO\u003csub\u003e5\u003c/sub\u003e","MolecularWeight":"581.7 g/mol","Pharmacodynamics":"Ergotamine is a vasoconstrictor and alpha adrenoreceptor antagonist. The pharmacological properties of ergotamine are extremely complex; some of its actions are unrelated to each other, and even mutually antagonistic. The drug has partial agonist and/or antagonist activity against tryptaminergic, dopaminergic and alpha adrenergic receptors depending upon their site, and it is a highly active uterine stimulant. It causes constriction of peripheral and cranial blood vessels and produces depression of central vasomotor centers. The pain of a migraine attack is believed to be due to greatly increased amplitude of pulsations in the cranial arteries, especially the meningeal branches of the external carotid artery. Ergotamine reduces extracranial blood flow, causes a decline in the amplitude of pulsation in the cranial arteries, and decreases hyperperfusion of the territory of the basilar artery. It does not reduce cerebral hemispheric blood flow.","Physical Description":"Highly hygroscopic solid; [Merck Index]","PubChemId":8223,"RefCount":2,"RefCur":"","References":[{"Name":"Wikipedia","Urls":[{"Link":"https://en.wikipedia.org/wiki/Ergotamine","Name":"Ergotamine","Sub":false}]},{"Name":"DrugBank","Urls":[{"Link":"https://go.drugbank.com/drugs/DB00696","Name":"Ergotamine","Sub":false}]},{"Name":"PubChem","Urls":[{"Link":"https://pubchem.ncbi.nlm.nih.gov/compound/8223","Name":"Ergotamine","Sub":false}]},{"Name":"ChEMBL","Urls":[{"Link":"https://www.ebi.ac.uk/chembl/explore/compound/CHEMBL442","Name":"Ergotamine","Sub":false}]},{"Name":"ChEBI","Urls":[{"Link":"https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:64318","Name":"Ergotamine","Sub":false}]},{"Name":"Common Chemistry","Urls":[{"Link":"https://commonchemistry.cas.org/detail?cas_rn=113-15-5","Name":"Ergotamine","Sub":false}]},{"Name":"HMDB","Urls":[{"Link":"https://hmdb.ca/metabolites/HMDB0014834","Name":"Ergotamine","Sub":false}]},{"Name":"KEGG","Urls":[{"Link":"https://www.kegg.jp/entry/D07906","Name":"Ergotamine","Sub":false}]},{"Name":"UNII","Urls":[{"Link":"https://gsrs.ncats.nih.gov/ginas/app/ui/substances/PR834Q503T","Name":"Ergotamine","Sub":false}]},{"Name":"EPA DSSTox","Urls":[{"Link":"https://comptox.epa.gov/dashboard/chemical/details/DTXSID9043774","Name":"Ergotamine","Sub":false}]}],"Refs":["National Center for Biotechnology Information. PubChem Compound Summary for CID 8223, Ergotamine. Accessed July 27, 2025. \u003ca href=https://pubchem.ncbi.nlm.nih.gov/compound/8223\u003ehttps://pubchem.ncbi.nlm.nih.gov/compound/8223\u003c/a\u003e"],"SMILES":"C[C@@]1(C(=O)N2[C@H](C(=O)N3CCC[C@H]3[C@@]2(O1)O)CC4=CC=CC=C4)NC(=O)[C@H]5CN([C@@H]6CC7=CNC8=CC=CC(=C78)C6=C5)C","SaltData":[],"Salts":[],"Solubility":"Slight","Stability/Shelf Life":"Stable under recommended storage conditions. /Ergotamine tartrate/","StereoisomerData":[],"Stereoisomers":[],"Structure":"\u003csvg xmlns=\"http://www.w3.org/2000/svg\" preserveAspectRatio=\"none\" style=\"display:block\" viewBox=\"0 0 136.695 182.698\"\u003e\u003crect width=\"100%\" height=\"100%\" fill=\"#fff\"/\u003e\u003cdesc\u003eGenerated by the Chemistry Development Kit (http://github.com/cdk)\u003c/desc\u003e\u003cg fill=\"#3050f8\" stroke=\"#000\" stroke-linecap=\"round\" stroke-linejoin=\"round\" stroke-width=\".7\"\u003e\u003cpath fill=\"#fff\" stroke=\"none\" d=\"M0 0h137v183H0z\"/\u003e\u003cg class=\"mol\"\u003e\u003cpath 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