{"ATC Code":["C - Cardiovascular system","C01 - Cardiac therapy","C01C - Cardiac stimulants excl. cardiac glycosides","C01CA - Adrenergic and dopaminergic agents","C01CA15 - Gepefrine","QC - Cardiovascular system","QC01 - Cardiac therapy","QC01C - Cardiac stimulants excl. cardiac glycosides","QC01CA - Adrenergic and dopaminergic agents","QC01CA15 - Gepefrine"],"Aliases":["gepefrina","Gepefrin","Dtxsid60172191","α-Methyl-m-tyramine","gepefrinum","3-hydroxyamphetamine","α-methyl-meta-tyramine","Dtxcid7094682","C01CA15","3-(2-Aminopropyl)phenol","Mfcd20458539","α-methyl-m-tyramine","m-(2-Aminopropyl)phenol","Unii-v51rrx51vh","3-(2-Amino-propyl)-phenol","Metaraminol Impurity 50","Schembl149774","orb3137129","Chembl3989731","DB13703","m-(2-Aminopropyl)-phenol.","DA-73702","SY410349","HY-107354","CS-0028203","NS00005661","Phenol, 3-((2s)-2-aminopropyl)-","Phenol, 3-(2-aminopropyl)-, (s)-","D07150","T73216","En300-1847493","Phenol, m-(2-aminopropyl)-, (s)-(+)-","(α-S)-(+)-α-methyl-m-tyramine"],"CAS":"18840-47-6","ChemicalClasses":["amphetamine"],"Chirality":"absolute","Classes":["Sympathomimetic"],"EliminationHalfLife":"","Erowid Experience Reports":[],"Esters":[],"Formating":[],"HeavyAtomCount":11,"IUPACName":"3-[(2S)-2-aminopropyl]phenol","InChI":"InChI=1S/C9H13NO/c1-7(10)5-8-3-2-4-9(11)6-8/h2-4,6-7,11H,5,10H2,1H3/t7-/m0/s1","InChIKey":"WTDGMHYYGNJEKQ-ZETCQYMHSA-N","KEGG Entries":[{"Id":"D07150","Interactions":[],"Synonyms":["Gepefrine"]},{"Id":"D07150","Interactions":[],"Synonyms":["Gepefrine"]}],"MeSH Headers":[{"Id":"M0131929","Link":"https://id.nlm.nih.gov/mesh/M0131929.html","Name":"gepefrine","Ref":18},{"Id":"DescTree","Link":"https://www.nlm.nih.gov/mesh/meshhome.html","Name":"MeSH Tree","Ref":20},{"Id":"PubMed from MeSH","Link":"https://www.nlm.nih.gov/mesh/meshhome.html","Name":null,"Ref":33}],"MolecularFormula":"C\u003csub\u003e9\u003c/sub\u003eH\u003csub\u003e13\u003c/sub\u003eNO","MolecularWeight":"151.21 g/mol","Opticalactivity":"UNSPECIFIED","PubChemId":219105,"Records":{"UNII":{"Impurities":[]}},"RefChem":"142952","RefCount":3,"RefCur":"","References":[{"Name":"Wikipedia","Urls":[{"Link":"https://en.wikipedia.org/wiki/Gepefrine","Name":"Gepefrine","Sub":false}]},{"Name":"Wikidata","Urls":[{"Link":"https://www.wikidata.org/wiki/Q23714168","Name":"Gepefrine","Sub":false}]},{"Name":"DrugBank","Urls":[{"Link":"https://go.drugbank.com/DB13703","Name":"Gepefrine","Sub":false}]},{"Name":"PubChem","Urls":[{"Link":"https://pubchem.ncbi.nlm.nih.gov/compound/219105","Name":"Gepefrine","Sub":false}]},{"Name":"Common Chemistry","Urls":[{"Link":"https://commonchemistry.cas.org/detail?cas_rn=18840-47-6","Name":"Gepefrine","Sub":false}]},{"Name":"KEGG","Urls":[{"Link":"https://www.kegg.jp/entry/D07150","Name":"Gepefrine","Sub":false}]},{"Name":"UNII","Urls":[{"Link":"https://gsrs.ncats.nih.gov/ginas/app/ui/substances/V51RRX51VH","Name":"Gepefrine","Sub":false}]},{"Name":"EPA DSSTox","Urls":[{"Link":"https://comptox.epa.gov/dashboard/chemical/details/DTXSID60172191","Name":"Gepefrine","Sub":false}]}],"Refs":["National Center for Biotechnology Information. PubChem Compound Summary for CID 219105, Gepefrine. Accessed May 6, 2026. \u003ca href=https://pubchem.ncbi.nlm.nih.gov/compound/219105\u003ehttps://pubchem.ncbi.nlm.nih.gov/compound/219105\u003c/a\u003e","U.S. Food and Drug Administration; National Center for Advancing Translational Sciences. Gepefrine. UNII: V51RRX51VH. Global Substance Registration System. Accessed May 6, 2026. \u003ca href=https://gsrs.ncats.nih.gov/ginas/app/beta/substances/V51RRX51VH\u003ehttps://gsrs.ncats.nih.gov/ginas/app/beta/substances/V51RRX51VH\u003c/a\u003e"],"SMILES":"C[C@@H](CC1=CC(=CC=C1)O)N","SaltData":[],"Salts":[],"Scheduling":[],"StereoisomerData":[],"Stereoisomers":[],"Structure":"\u003csvg xmlns=\"http://www.w3.org/2000/svg\" preserveAspectRatio=\"none\" style=\"display:block\" viewBox=\"0 0 95.633 34.614\"\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 0h96v35H0z\"/\u003e\u003cg class=\"mol\"\u003e\u003cpath fill=\"#000\" stroke=\"none\" d=\"M73.473 10.707h-.7l-1.751 15.24h4.201z\" class=\"bond\"/\u003e\u003cpath d=\"m73.123 10.707-13.199-7.62M59.924 3.087l-13.198 7.62\" class=\"bond\"/\u003e\u003cg class=\"bond\"\u003e\u003cpath d=\"M46.726 10.707 33.523 3.079M44.288 12.115l-10.765-6.22\"/\u003e\u003c/g\u003e\u003cpath d=\"m33.523 3.079-13.198 7.62\" class=\"bond\"/\u003e\u003cg class=\"bond\"\u003e\u003cpath d=\"m20.325 10.699.005 15.248M22.764 12.107l.004 12.433\"/\u003e\u003c/g\u003e\u003cpath d=\"m20.33 25.947 13.203 7.629\" class=\"bond\"/\u003e\u003cg class=\"bond\"\u003e\u003cpath d=\"m33.533 33.576 13.198-7.62M33.533 30.76l10.759-6.212\"/\u003e\u003c/g\u003e\u003cpath d=\"m46.726 10.707.005 15.249M20.325 10.699l-9.924-5.727M73.123 10.707l10.045-5.799\" class=\"bond\"/\u003e\u003cg fill=\"#ff0d0d\" stroke=\"none\" class=\"atom\"\u003e\u003cpath d=\"M9.385 3.078q0 .756-.256 1.328-.256.565-.756.881-.5.315-1.245.315-.756 0-1.262-.315-.506-.316-.756-.887-.244-.572-.244-1.334 0-.75.244-1.309.25-.566.756-.881T7.14.56q.733 0 1.233.316.5.309.756.875.256.565.256 1.327m-3.864 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 1.452M4.305 5.531h-.62V3.245H1.173v2.286H.56v-4.9h.613v2.072h2.512V.631h.62z\"/\u003e\u003c/g\u003e\u003cg stroke=\"none\" class=\"atom\"\u003e\u003cpath d=\"M88.262 5.537h-.721l-2.619-4.066h-.03l.03.596q.024.357.024.732v2.738h-.566V.638h.715l2.607 4.054h.03l-.018-.328-.024-.476q-.006-.262-.006-.482V.638h.578zM92.568 5.537h-.619V3.251h-2.513v2.286h-.613V.638h.613v2.071h2.513V.638h.619zM95.073 7.027h-1.944v-.3l.772-.779q.221-.221.371-.393.154-.175.233-.339.078-.168.078-.365 0-.242-.146-.367-.143-.129-.372-.129-.214 0-.378.075-.161.075-.329.207l-.193-.243q.172-.146.393-.246.225-.1.507-.1.411 0 .65.207t.24.575q0 .229-.097.432-.093.2-.264.397-.168.196-.393.418l-.614.603v.018h1.486z\"/\u003e\u003c/g\u003e\u003cpath stroke=\"#ff0d0d\" d=\"m10.401 4.972 4.962 2.863M10.401 4.972l4.962 2.863\" class=\"hi\"/\u003e\u003cpath stroke=\"#3050f8\" d=\"m83.168 4.908-5.023 2.9\" 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":"Gepefrine","UNII":"V51RRX51VH","Wikidata":"Q23714168","Wikipedia":"Gepefrine","XLogP":1.4}