{"Abbreviation":["LAA","LA-111"],"Aliases":["Lysergamide","CHEBI:4819","9,10-didehydro-6-methylergoline-8 β-carboxamide","(8R)-9,10-didehydro-6-methylergoline-8-carboxamide","(6aR,9R)-7-methyl-6,6a,8,9-tetrahydro-4H-indolo(4,3-fg)quinoline-9-carboxamide","207-524-0","Ergine","9,10-Didehydro-6-methylergoline-8β-carboxamide","(6aR,9R)-7-methyl-4,6,6a,7,8,9-hexahydroindolo[4,3-fg]quinoline-9-carboxamide","Lyergic acid amide","Einecs 207-524-0","Brn 0090708","4-25-00-00937","Schembl183540","9,10-Didehydro-6-methyl-ergoline-8-β-carboxamide","Chembl227213","DEA No. 7310","Ergoline-8-β-carboxamide, 9,10-didehydro-6-methyl-","Pdsp2_001113","Akos030240648","Methylergometrine Maleate EP Impurity C","DB-230603","NS00042929","C09160","6-Methyl-9,10-didehydroergoline-8β-carboxamide","Ergometrine maleate impurity c","(8β)-6-methyl-9,10-didehydroergoline-8-carboxamide","(8β)-9,10-Didehydro-6-methylergoline-8-carboxamide","(4R,7R)-6-methyl-6,11-diazatetracyclo[7.6.1.0?,?.0??,??]hexadeca-1(15),2,9,12(16),13-pentaene-4-carboxamide"],"CAS":"478-94-4","ChemicalClasses":["lysergamide"],"Chirality":"absolute","Classes":["Psychedelic"],"DTXSID":"RefChem:800201","DurationOfAction":"4 – 10 h (morning glory|morn. glory seeds)\u003ca href='#cite_note-4'\u003e\u003csup\u003e[4]\u003c/sup\u003e\u003c/a\u003e","EliminationHalfLife":"","Erowid Experience Reports":[],"Esters":[],"European Community (EC) Number":"207-524-0","Formating":[],"Health Effects":"Ingestion of ergoline alkaloids is known to cause the disease ergotism. Ergotism occurs in two forms, gangrenous and convulsive, likely depending on the different kinds and amounts of ergoline alkaloids present. (A2913)","HeavyAtomCount":20,"IUPACName":"(6aR,9R)-7-methyl-6,6a,8,9-tetrahydro-4H-indolo[4,3-fg]quinoline-9-carboxamide","InChI":"InChI=1S/C16H17N3O/c1-19-8-10(16(17)20)5-12-11-3-2-4-13-15(11)9(7-18-13)6-14(12)19/h2-5,7,10,14,18H,6,8H2,1H3,(H2,17,20)/t10-,14-/m1/s1","InChIKey":"GENAHGKEFJLNJB-QMTHXVAHSA-N","MeSH Headers":[{"Id":"M0066631","Link":"https://id.nlm.nih.gov/mesh/M0066631.html","Name":"lysergamide","Ref":28},{"Id":"DescTree","Link":"https://www.nlm.nih.gov/mesh/meshhome.html","Name":"MeSH Tree","Ref":29},{"Id":"PubMed from MeSH","Link":"https://www.nlm.nih.gov/mesh/meshhome.html","Name":null,"Ref":43}],"MolecularFormula":"C\u003csub\u003e16\u003c/sub\u003eH\u003csub\u003e17\u003c/sub\u003eN\u003csub\u003e3\u003c/sub\u003eO","MolecularWeight":"267.33 g/mol","Opticalactivity":"UNSPECIFIED","PubChemId":442072,"Records":{"UNII":{"Impurities":[]}},"RefChem":"800201","RefCount":5,"RefCur":"","References":[{"Name":"Wikipedia","Urls":[{"Link":"https://en.wikipedia.org/wiki/Ergine","Name":"Ergine","Sub":false}]},{"Name":"Wikidata","Urls":[{"Link":"https://www.wikidata.org/wiki/Q2041643","Name":"Ergine","Sub":false}]},{"Name":"PubChem","Urls":[{"Link":"https://pubchem.ncbi.nlm.nih.gov/compound/442072","Name":"Ergine","Sub":false}]},{"Name":"Common Chemistry","Urls":[{"Link":"https://commonchemistry.cas.org/detail?cas_rn=478-94-4","Name":"Ergine","Sub":false}]},{"Name":"KEGG","Urls":[{"Link":"https://www.kegg.jp/entry/C09160","Name":"Ergine","Sub":false}]},{"Name":"UNII","Urls":[{"Link":"https://gsrs.ncats.nih.gov/ginas/app/ui/substances/073830XH10","Name":"Ergine","Sub":false}]},{"Name":"EPA DSSTox","Urls":[{"Link":"https://comptox.epa.gov/dashboard/chemical/details/DTXSID20893673","Name":"Ergine","Sub":false}]}],"Refs":["National Center for Biotechnology Information. PubChem Compound Summary for CID 442072, Lysergamide. Accessed May 17, 2026. \u003ca href=https://pubchem.ncbi.nlm.nih.gov/compound/442072\u003ehttps://pubchem.ncbi.nlm.nih.gov/compound/442072\u003c/a\u003e","U.S. Food and Drug Administration; National Center for Advancing Translational Sciences. Ergine. UNII: 073830XH10. Global Substance Registration System. Accessed May 17, 2026. \u003ca href=https://gsrs.ncats.nih.gov/ginas/app/beta/substances/073830XH10\u003ehttps://gsrs.ncats.nih.gov/ginas/app/beta/substances/073830XH10\u003c/a\u003e","Anvisa. RDC Nº 804 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial. Diário Oficial da União. July 24, 2023. Accessed May 17, 2026. \u003ca href=https://www.in.gov.br/en/web/dou/-/resolucao-rdc-n-804-de-24-de-julho-de-2023-498447451\u003ehttps://www.in.gov.br/en/web/dou/-/resolucao-rdc-n-804-de-24-de-julho-de-2023-498447451\u003c/a\u003e","Tittarelli R, Mannocchi G, Pantano F, Romolo FS. Recreational use, analysis and toxicity of tryptamines. Curr Neuropharmacol. January 1, 2015; 13(1):26–46."],"SMILES":"CN1C[C@@H](C=C2[C@H]1CC3=CNC4=CC=CC2=C34)C(=O)N","SaltData":[],"Salts":[],"Scheduling":[{"gov":"Brazil","ref":["3"],"schedule":"F2 substance"},{"act":"Neue-psychoaktive-Stoffe-Gesetz (NpSG)","gov":"Germany","ref":[],"schedule":"Neuer-Psychoaktiver-Stoff"},{"gov":"United Kingdom","ref":[],"schedule":"Class A substance"},{"act":"Controlled Substances Act (CSA)","gov":"United States","ref":[],"schedule":"Schedule I"}],"StereoisomerData":[],"Stereoisomers":[],"Structure":"\u003csvg xmlns=\"http://www.w3.org/2000/svg\" preserveAspectRatio=\"none\" style=\"display:block\" viewBox=\"0 0 81.304 98.252\"\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 0h82v99H0z\"/\u003e\u003cg class=\"mol\"\u003e\u003cpath d=\"m80.266 57.461-10.049-5.795M67.062 45.998l-.005-11.389M67.057 34.609l-13.2-7.615M53.857 26.994l-13.195 7.622\" class=\"bond\"/\u003e\u003cg class=\"bond\"\u003e\u003cpath d=\"M40.662 34.616v15.24M43.1 36.023l.001 12.424\"/\u003e\u003c/g\u003e\u003cpath d=\"m40.662 49.856 13.208 7.62\" class=\"bond\"/\u003e\u003cg class=\"bond\"\u003e\u003cpath d=\"m53.695 57.173.35.606M55.748 55.649l.642 1.111M57.801 54.125l.934 1.616M59.853 52.601l1.227 2.121M61.906 51.077l1.519 2.626\"/\u003e\u003cpath stroke=\"#3050f8\" d=\"m63.425 53.703-.76-1.313\" class=\"hi\"/\u003e\u003c/g\u003e\u003cpath d=\"M53.87 57.476v15.24M53.87 72.716 38.773 82.921\" class=\"bond\"/\u003e\u003cg class=\"bond\"\u003e\u003cpath d=\"m32.57 96.839 6.203-13.918M31.063 94.229l4.762-10.683\"/\u003e\u003c/g\u003e\u003cpath d=\"m32.57 96.839-11.822-1.245M16.603 91.423l-2.357-11.087\" class=\"bond\"/\u003e\u003cg class=\"bond\"\u003e\u003cpath d=\"m1.038 72.716 13.208 7.62M3.477 71.307l10.769 6.214\"/\u003e\u003c/g\u003e\u003cpath d=\"M1.038 72.716v-15.24\" class=\"bond\"/\u003e\u003cg class=\"bond\"\u003e\u003cpath d=\"m14.246 49.856-13.208 7.62M14.246 52.671 3.477 58.884\"/\u003e\u003c/g\u003e\u003cpath d=\"m14.246 49.856 13.208 7.62M40.662 49.856l-13.208 7.62\" class=\"bond\"/\u003e\u003cg class=\"bond\"\u003e\u003cpath d=\"M27.454 72.716v-15.24M25.016 71.307V58.884\"/\u003e\u003c/g\u003e\u003cpath d=\"M38.773 82.921 27.454 72.716M14.246 80.336l13.208-7.62\" class=\"bond\"/\u003e\u003cpath fill=\"#000\" stroke=\"none\" d=\"M53.507 26.994h.7l1.895-16.539-2.249 1.3-2.249-1.299z\" class=\"bond\"/\u003e\u003cg class=\"bond\"\u003e\u003cpath d=\"m53.853 11.754-9.924-5.727M53.853 8.938l-8.705-5.023\"/\u003e\u003cpath stroke=\"#ff0d0d\" d=\"m43.929 6.027 4.962 2.863M45.148 3.915l4.353 2.512\" class=\"hi\"/\u003e\u003c/g\u003e\u003cpath d=\"m53.853 11.754 10.043-5.802\" class=\"bond\"/\u003e\u003cpath stroke=\"none\" d=\"M69.004 52.297h-.72l-2.62-4.066h-.029l.029.595q.024.358.024.733v2.738h-.565v-4.899h.714l2.607 4.054h.03l-.018-.328q-.012-.22-.023-.476-.006-.262-.006-.482v-2.768h.577z\" class=\"atom\"/\u003e\u003cg stroke=\"none\" class=\"atom\"\u003e\u003cpath d=\"M19.356 97.692h-.721l-2.619-4.066h-.03l.03.596q.024.357.024.732v2.738h-.566v-4.899h.715l2.607 4.054h.03l-.018-.327-.024-.477q-.006-.262-.006-.482v-2.768h.578zM14.912 97.692h-.619v-2.286h-2.512v2.286h-.613v-4.899h.613v2.072h2.512v-2.072h.619z\"/\u003e\u003c/g\u003e\u003cpath fill=\"#ff0d0d\" stroke=\"none\" d=\"M43.521 3.078q0 .756-.255 1.328-.256.565-.757.881-.5.315-1.244.315-.756 0-1.262-.315-.506-.316-.756-.887-.244-.572-.244-1.334 0-.75.244-1.309.25-.566.756-.881T41.277.56q.732 0 1.232.316.501.309.757.875.255.565.255 1.327m-3.863 0q0 .923.387 1.459.393.53 1.22.53.84 0 1.221-.53.387-.536.387-1.459 0-.929-.387-1.452-.381-.524-1.209-.524-.833 0-1.226.524-.393.523-.393 1.452\" class=\"atom\"/\u003e\u003cg stroke=\"none\" class=\"atom\"\u003e\u003cpath d=\"M68.99 6.58h-.72l-2.62-4.066h-.029l.029.595q.024.357.024.732V6.58h-.565v-4.9h.714l2.608 4.054h.029l-.018-.327-.023-.476q-.006-.262-.006-.483V1.68h.577zM73.296 6.58h-.619V4.294h-2.512V6.58h-.613v-4.9h.613v2.072h2.512V1.68h.619zM75.801 8.069h-1.943v-.3l.772-.779q.221-.221.371-.392.154-.175.232-.34.079-.168.079-.364 0-.243-.147-.368-.143-.129-.371-.129-.214 0-.379.075-.161.075-.328.208l-.193-.243q.171-.147.393-.247.225-.1.507-.1.411 0 .65.207.239.208.239.575 0 .229-.096.433-.093.2-.265.396-.167.197-.392.418l-.615.604v.018h1.486z\"/\u003e\u003c/g\u003e\u003cpath stroke=\"#3050f8\" d=\"m70.217 51.666 5.025 2.897M67.062 45.998l-.003-5.695M20.748 95.594l5.911.622M20.748 95.594l5.911.622M16.603 91.423l-1.178-5.543M16.603 91.423l-1.178-5.543M63.896 5.952l-5.022 2.901\" class=\"hi\"/\u003e\u003c/g\u003e\u003c/g\u003e\u003c/svg\u003e","Subjective Effects":null,"Title":"Ergine","Treatment":"Treatment for ergotism consists of vasodilators, anticoagulants and low molecular weight dextrans. If necessary, a sympathetic nerve blockade may be carried out, such as brachial plexus blockade. Temporary sedation (e.g. haloperidol) will be necessary in hallucination and diazepam is used for convulsions. There is no specific antidote. (L1921)","UNII":"073830XH10","Wikidata":"Q2041643","Wikipedia":"Ergine","XLogP":1.6}