{"ATC Code":["A - Alimentary tract and metabolism","A03 - Drugs for functional gastrointestinal disorders","A03A - Drugs for functional gastrointestinal disorders","A03AX - Other drugs for functional gastrointestinal disorders","A03AX10 - Isometheptene","QA - Alimentary tract and metabolism","QA03 - Drugs for functional gastrointestinal disorders","QA03A - Drugs for functional gastrointestinal disorders","QA03AX - Other drugs for functional gastrointestinal disorders","QA03AX10 - Isometheptene"],"Aliases":["Octanil","Isonyl","Octin","6-Methylamino-2-methylheptene","5-Hepten-2-amine, N,6-dimethyl-","Isometepteno","Isometheptenum","Methyloctenylamine","methyl(6-methylhept-5-en-2-yl)amine","N,6-Dimethyl-5-hepten-2-amine","N,1,5-Trimethyl-4-hexenylamine","2-Methyl-6-methylamino-2-heptene","4-Hexenylamine, N,1,5-trimethyl-","isometeptene","Dtxcid403172","A03AX10","207-959-6","Octinum","Octon","Methylisooctenylamine","Isonyl; Octanil; Octin; Octine; Octinum","Octine","Einecs 207-959-6","Brn 1742093","Ec 207-959-6","Schembl148619","Chembl1697841","Chebi:134765","6-Methylamino-2-methyl-2-heptene","MSK11454","N,6-Dimethyl-5-hepten-2-amine #","EBC-26082","Akos006275249","DB06706","AB00514747","NS00001229","En300-6430800","Sr-01000944473","Sr-01000944473-1","Brd-a64743628-001-01-5"],"CAS":"503-01-5","ChemicalClasses":["amine"],"Chirality":"racemic","Classes":["Sympathomimetic"],"DTXSID":"9023172","Drug Indication":"Isometheptene is a sympathomimetic drug which causes vasoconstriction. It is used for treating migraines and tension headaches.","EliminationHalfLife":"","Erowid Experience Reports":[],"Esters":[],"European Community (EC) Number":"207-959-6","Formating":[],"HMDB ID":"HMDB0015651","HeavyAtomCount":10,"Human Drugs":"Pharmaceuticals","IUPACName":"N,6-dimethylhept-5-en-2-amine","InChI":"InChI=1S/C9H19N/c1-8(2)6-5-7-9(3)10-4/h6,9-10H,5,7H2,1-4H3","InChIKey":"XVQUOJBERHHONY-UHFFFAOYSA-N","MeSH Headers":[{"Id":"M0051833","Link":"https://id.nlm.nih.gov/mesh/M0051833.html","Name":"isometheptene","Ref":39},{"Id":"DescTree","Link":"https://www.nlm.nih.gov/mesh/meshhome.html","Name":"MeSH Tree","Ref":41},{"Id":"PubMed from MeSH","Link":"https://www.nlm.nih.gov/mesh/meshhome.html","Name":null,"Ref":59}],"Mechanism of Action":"Isometheptene's vasoconstricting properties arise through activation of the sympathetic nervous system via epinephrine and norepinephrine (or their molecular analogues as is the case with this drug). These compounds elicites smooth muscle activation leading to vasoconstriction. These compounds interact with cell surface adrenergic receptors. Such stimuli result in a signal transduction cascade that leads to increased intracellular calcium from the sarcoplasmic reticulum through IP3 mediated calcium release, as well as enhanced calcium entry across the sarcolemma through calcium channels. The rise in intracellular calcium complexes with calmodulin, which in turn activates myosin light chain kinase. This enzyme is responsible for phosphorylating the light chain of myosin to stimulate cross bridge cycling.  Once elevated, the intracellular calcium concentration is returned to its basal level through a variety of protein pumps and calcium exchangers located on the plasma membrane and sarcoplasmic reticulum. This reduction in calcium removes the stimulus necessary for contraction allowing for a return to baseline. The drug can also cause vesicular displacement of noradrenaline from the neuron into the synapse with a similar effect as tyramine.","MolecularFormula":"C\u003csub\u003e9\u003c/sub\u003eH\u003csub\u003e19\u003c/sub\u003eN","MolecularWeight":"141.25 g/mol","Opticalactivity":"( + / - )","Pharmacodynamics":"Isometheptene Mucate is an indirect-acting sympathomimetic. Due to its vasoconstricting properties, Isometheptene Mucate is used for the treatment of acute migraine attacks, usually in combination with other analgeics. It can also displace catecholamines from vesicles inside the neuron leading to the sympathetic responses it is known for.","Physical Description":"Solid","PubChemId":22297,"PubChemTitle":"Isometheptene","Record Description":["LiverTox|CNS|Migraine|Sympathomimetic amine"],"Records":{"UNII":{"Impurities":[]}},"Reddit Experience Reports":[],"RefChem":"149544","RefCount":3,"RefCur":"","References":[{"Name":"Wikipedia","Urls":[{"Link":"https://en.wikipedia.org/wiki/Isometheptene","Name":"Isometheptene","Sub":false}]},{"Name":"Wikidata","Urls":[{"Link":"https://www.wikidata.org/wiki/Q1098951","Name":"Isometheptene","Sub":false}]},{"Name":"DrugBank","Urls":[{"Link":"https://go.drugbank.com/DB06706","Name":"Isometheptene","Sub":false}]},{"Name":"PubChem","Urls":[{"Link":"https://pubchem.ncbi.nlm.nih.gov/compound/22297","Name":"Isometheptene","Sub":false}]},{"Name":"Common Chemistry","Urls":[{"Link":"https://commonchemistry.cas.org/detail?cas_rn=503-01-5","Name":"Isometheptene","Sub":false}]},{"Name":"HMDB","Urls":[{"Link":"https://hmdb.ca/metabolites/HMDB0015651","Name":"Isometheptene","Sub":false}]},{"Name":"UNII","Urls":[{"Link":"https://gsrs.ncats.nih.gov/ginas/app/ui/substances/Y7L24THH6T","Name":"Isometheptene","Sub":false}]},{"Name":"EPA DSSTox","Urls":[{"Link":"https://comptox.epa.gov/dashboard/chemical/details/DTXSID9023172","Name":"Isometheptene","Sub":false}]}],"Refs":["National Center for Biotechnology Information. PubChem Compound Summary for CID 22297, Isometheptene. Accessed August 22, 2026. \u003ca href=https://pubchem.ncbi.nlm.nih.gov/compound/22297\u003ehttps://pubchem.ncbi.nlm.nih.gov/compound/22297\u003c/a\u003e","U.S. Food and Drug Administration; National Center for Advancing Translational Sciences. Isometheptene. UNII: Y7L24THH6T. Global Substance Registration System. Accessed August 22, 2026. \u003ca href=https://gsrs.ncats.nih.gov/ginas/app/beta/substances/Y7L24THH6T\u003ehttps://gsrs.ncats.nih.gov/ginas/app/beta/substances/Y7L24THH6T\u003c/a\u003e"],"SMILES":"CC(CCC=C(C)C)NC","SaltData":[{"AcidCount":1,"Amine":"Isometheptene","AmineCount":1,"Formula":"Cl","Name":"hydrochloride","RName":"hydrochloride","Structure":"\u003csvg xmlns=\"http://www.w3.org/2000/svg\" preserveAspectRatio=\"none\" style=\"display:block\" viewBox=\"0 0 118.146 32.452\"\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=\"#1ff01f\" stroke=\"#000\" stroke-linecap=\"round\" stroke-linejoin=\"round\" stroke-width=\".8\"\u003e\u003cpath fill=\"#fff\" stroke=\"none\" d=\"M0 0h119v33H0z\"/\u003e\u003cg class=\"mol\"\u003e\u003cpath d=\"M67.098 31.492v-15.24M67.098 16.252l-13.199-7.62M53.899 8.632l-13.198 7.62M40.701 16.252l-13.198-7.62\" 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0-1.209.649-1.899.655-.697 1.792-.697.446 0 .839.119.399.119.75.357m1.021-.595h.613v5.209h-.613zM107.541 13.782h.678v2.048h2.459v-2.048h.673v5.001h-.673v-2.381h-2.459v2.381h-.678z\"/\u003e\u003c/g\u003e\u003c/g\u003e\u003c/g\u003e\u003c/svg\u003e","Title":"Isometheptene hydrochloride","UNII":"9Z4CJC3O5F"}],"Salts":["hydrochloride"],"Scheduling":[],"StereoisomerData":[{"ChemicalClasses":["amine"],"SMILES":"CN[C@H](C)CCC=C(C)C","Structure":"\u003csvg xmlns=\"http://www.w3.org/2000/svg\" preserveAspectRatio=\"none\" style=\"display:block\" viewBox=\"0 0 94.601 32.452\"\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=\".8\"\u003e\u003cpath fill=\"#fff\" stroke=\"none\" d=\"M0 0h95v33H0z\"/\u003e\u003cg class=\"mol\"\u003e\u003cpath d=\"m93.494 16.252-9.913-5.723M77.017 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class=\"hi\"/\u003e\u003c/g\u003e\u003c/g\u003e\u003c/svg\u003e","Title":"(R)-Isometheptene"},{"ChemicalClasses":["amine"],"SMILES":"CN[C@@H](C)CCC=C(C)C","Structure":"\u003csvg xmlns=\"http://www.w3.org/2000/svg\" preserveAspectRatio=\"none\" style=\"display:block\" viewBox=\"0 0 94.601 32.452\"\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=\".8\"\u003e\u003cpath fill=\"#fff\" stroke=\"none\" d=\"M0 0h95v33H0z\"/\u003e\u003cg class=\"mol\"\u003e\u003cpath d=\"m93.494 16.252-9.913-5.723M77.017 10.526l-9.919 5.726\" class=\"bond\"/\u003e\u003cpath fill=\"#000\" stroke=\"none\" d=\"M67.498 16.252h-.8l-2.001 15.24h4.801z\" class=\"bond\"/\u003e\u003cpath d=\"m67.098 16.252-13.199-7.62M53.899 8.632l-13.198 7.62M40.701 16.252l-13.198-7.62\" class=\"bond\"/\u003e\u003cg 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(http://github.com/cdk)\u003c/desc\u003e\u003cg fill=\"#3050f8\" stroke=\"#000\" stroke-linecap=\"round\" stroke-linejoin=\"round\" stroke-width=\".8\"\u003e\u003cpath fill=\"#fff\" stroke=\"none\" d=\"M0 0h95v33H0z\"/\u003e\u003cg class=\"mol\"\u003e\u003cpath d=\"M67.098 31.492v-15.24M67.098 16.252l-13.199-7.62M53.899 8.632l-13.198 7.62M40.701 16.252l-13.198-7.62\" class=\"bond\"/\u003e\u003cg class=\"bond\"\u003e\u003cpath d=\"m27.503 8.632-13.198 7.62M27.503 11.448l-10.76 6.212\"/\u003e\u003c/g\u003e\u003cpath d=\"M14.305 16.252 1.106 8.632M14.305 16.252v15.24M67.098 16.252l9.919-5.726M83.581 10.529l9.913 5.723\" class=\"bond\"/\u003e\u003cg stroke=\"none\" class=\"atom\"\u003e\u003cpath d=\"M78.403 6.132h.911l2.214 4.185V6.132h.661v5.001h-.911l-2.22-4.185v4.185h-.655zM78.403.56h.678v2.048h2.459V.56h.673v5.001h-.673V3.179h-2.459v2.382h-.678z\"/\u003e\u003c/g\u003e\u003cpath stroke=\"#3050f8\" d=\"m77.017 10.526-4.959 2.863M83.581 10.529l4.956 2.861\" class=\"hi\"/\u003e\u003c/g\u003e\u003c/g\u003e\u003c/svg\u003e","Subjective Effects":{"Cognitive Effects":["Thought acceleration","Wakefulness"],"Physical Effects":["Stamina enhancement","Dehydration","Dry mouth","Restless legs","Shakiness","Abnormal heartbeat","Increased blood pressure","Increased heart rate","Vasoconstriction"],"Visual Effects":[]},"Title":"Isometheptene","UNII":"Y7L24THH6T","Wikidata":"Q1098951","Wikipedia":"Isometheptene","XLogP":2.5}