{"Abbreviation":"4-HEP","Aliases":["Methylsynephrin","Methylsympatol","Oxyephedrin","Methyl synephrin","Methyl synephrine","p-Hydroxyephedrine","Oxilofrinum","Oxyephedrine","Oxilofrina","Suprifene"],"CAS":"365-26-4","ChEBI":"CHEBI:134822","ChEMBL":"CHEMBL1160695","ChemicalClasses":["phenylethanolamine"],"Chirality":"racemic","Classes":["Sympathomimetic"],"Drug Indication":"Used in combination with [DB11609] as an antitussive.","DrugClasses":[],"EINECS":"206-672-3","EliminationHalfLife":"","Erowid Experience Reports":[],"European Community (EC) Number":"206-672-3","FullSalts":["Oxilofrine hydrochloride"],"HeavyAtomCount":13,"IUPACName":"4-[(1R,2S)-1-hydroxy-2-(methylamino)propyl]phenol","InChI":"InChI=1S/C10H15NO2/c1-7(11-2)10(13)8-3-5-9(12)6-4-8/h3-7,10-13H,1-2H3/t7-,10-/m0/s1","InChIKey":"OXFGTKPPFSCSMA-XVKPBYJWSA-N","MolecularFormula":"C\u003csub\u003e10\u003c/sub\u003eH\u003csub\u003e15\u003c/sub\u003eNO\u003csub\u003e2\u003c/sub\u003e","MolecularWeight":"181.23 g/mol","Opticalactivity":"( + / - )","Pharmacodynamics":"Oxilofrine is a sympathomimetic which increases adrenergic activity.","PrevSalts":["hydrochloride"],"PubChemId":688009,"Record Description":["Oxilofrine is an alkylbenzene.","Oxilofrine is used in combination with [DB11609] as an antitussive. It is currently marketed in Canada by Valeant under the tradename Cophylac.","Oxilofrine is an alkylbenzene."],"RefCount":5,"References":[{"Name":"Wikipedia","Urls":[{"Link":"https://en.wikipedia.org/wiki/Oxilofrine","Name":"Oxilofrine","Sub":false}]},{"Name":"Wikidata","Urls":[{"Link":"https://www.wikidata.org/wiki/Q1689157","Name":"Oxilofrine","Sub":false}]},{"Name":"DrugBank","Urls":[{"Link":"https://go.drugbank.com/drugs/DB11610","Name":"Oxilofrine","Sub":false}]},{"Name":"PubChem","Urls":[{"Link":"https://pubchem.ncbi.nlm.nih.gov/compound/688009","Name":"Oxilofrine","Sub":false}]},{"Name":"ChEMBL","Urls":[{"Link":"https://www.ebi.ac.uk/chembl/explore/compound/CHEMBL1160695","Name":"Oxilofrine","Sub":false}]},{"Name":"ChEBI","Urls":[{"Link":"https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:134822","Name":"Oxilofrine","Sub":false}]},{"Name":"Common Chemistry","Urls":[{"Link":"https://commonchemistry.cas.org/detail?cas_rn=365-26-4","Name":"Oxilofrine","Sub":false}]},{"Name":"UNII","Urls":[{"Link":"https://gsrs.ncats.nih.gov/ginas/app/ui/substances/F49638UBDR","Name":"Oxilofrine","Sub":false}]},{"Name":"EPA DSSTox","Urls":[{"Link":"https://comptox.epa.gov/dashboard/chemical/details/DTXSID30110025","Name":"Oxilofrine","Sub":false}]}],"Refs":["National Center for Biotechnology Information. PubChem Compound Summary for CID 688009, Oxilofrine. Accessed June 26, 2025. \u003ca href=https://pubchem.ncbi.nlm.nih.gov/compound/688009\u003ehttps://pubchem.ncbi.nlm.nih.gov/compound/688009\u003c/a\u003e","U.S. Food and Drug Administration; National Center for Advancing Translational Sciences. Oxilofrine. UNII: F49638UBDR. Global Substance Registration System. Accessed June 26, 2025. \u003ca href=https://gsrs.ncats.nih.gov/ginas/app/beta/substances/F49638UBDR\u003ehttps://gsrs.ncats.nih.gov/ginas/app/beta/substances/F49638UBDR\u003c/a\u003e","Anvisa. RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial. Diário Oficial da União. March 31, 2023. Accessed June 26, 2025. \u003ca href=https://www.in.gov.br/en/web/dou/-/resolucao-rdc-n-784-de-31-de-marco-de-2023-474904992\u003ehttps://www.in.gov.br/en/web/dou/-/resolucao-rdc-n-784-de-31-de-marco-de-2023-474904992\u003c/a\u003e","Methylsynephrine in Dietary Supplements. February 22, 2023. Accessed June 26, 2025. \u003ca href=https://www.fda.gov/food/dietary-supplement-ingredient-directory/methylsynephrine-dietary-supplements\u003ehttps://www.fda.gov/food/dietary-supplement-ingredient-directory/methylsynephrine-dietary-supplements\u003c/a\u003e"],"SMILES":"C[C@@H]([C@@H](C1=CC=C(C=C1)O)O)NC","Salts":["hydrochloride"],"SaltsAcidCount":[1],"SaltsAmineCount":[1],"SaltsUNII":["3O9694M5EO"],"Scheduling":[{"gov":"Brazil","ref":["3"],"schedule":"A3 substance"},{"gov":"United States","ref":["4"],"schedule":"Unapproved \"New Drug\" (as defined by 21 U.S. Code § 321(p)(1)). Use in dietary supplements, food, or medicine is unlawful; otherwise uncontrolled. substance"}],"Solubility":"Partly miscible","StereoisomerRacemic":"(RS)-Oxilofrine","StoreUNII":["F49638UBDR"],"StructureBase64":"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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"],"Sensory Effects":[]},"Title":"Oxilofrine","UNII":"F49638UBDR","Wikidata":"Q1689157","Wikipedia":"Oxilofrine","XLogP":0.6}