dioxifedrine

{{Short description|Sympathomimetic that was never marketed}}

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{{Distinguish|Dioxethedrin}}

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| CAS_number = 10329-60-9

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| PubChem = 13683

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| ChemSpiderID = 13093

| UNII = CF48QOH154

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| ChEMBL = 416557

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| synonyms = Dioxifedrin; α-Methylepinephrine; α-Methyladrenaline; 3,4-Dihydroxyephedrine; Dioxyephedrine; Sor-N 49; Diphedran; LD-1205; 3,4,β-Trihydroxy-α,N-dimethylphenethylamine; 3,4,β-Trihydroxy-N-methylamphetamine

| IUPAC_name = 4-[1-hydroxy-2-(methylamino)propyl]benzene-1,2-diol

| C=10 | H=15 | N=1 | O=3

| SMILES = CC(C(C1=CC(=C(C=C1)O)O)O)NC

| StdInChI = 1S/C10H15NO3/c1-6(11-2)10(14)7-3-4-8(12)9(13)5-7/h3-6,10-14H,1-2H3

| StdInChIKey = DDBFLXGTCAVAFD-UHFFFAOYSA-N

}}

Dioxifedrine ({{Abbrlink|INN|International Nonproprietary Name}}), or dioxifedrin, also known as α-methylepinephrine or as 3,4-dihydroxyephedrine, is a sympathomimetic medication that was never marketed.{{cite book | vauthors = Elks J | title=The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies | publisher=Springer US | year=2014 | isbn=978-1-4757-2085-3 | url=https://books.google.com/books?id=0vXTBwAAQBAJ&pg=PA447 | access-date=2 September 2024 | page=447}}{{cite web | title=Dioxifedrine | work = PubChem | publisher = U.S. National Library of Medicine | url=https://pubchem.ncbi.nlm.nih.gov/compound/13683 | access-date=2 September 2024}}{{cite web | url = https://iris.who.int/bitstream/handle/10665/67830/WHO_EDM_QSM_2003.2.pdf | title = The use of common stems in the selection of International Nonproprietary Names (INN) for pharmaceutical substances | date = 2002 | work = Programme on International Nonproprietary Names (INN) | publisher = World Health Organization (WHO) }}{{cite web | title = Dioxifedrine | work = CAS Common Chemistry | publisher = American Chemical Society | date=2 September 2024 | url=https://commonchemistry.cas.org/detail?cas_rn=10329-60-9 | access-date=2 September 2024 | id = CAS Registration Number 10329-60-9 }} It is described as a β-adrenergic receptor agonist and bronchodilator.{{cite web | title=DIOXIFEDRINE | work = Inxight Drugs | publisher = National Center for Advancing Translational Sciences (NCATS) | url=https://drugs-dev01.ncats.io/drug/CF48QOH154 | access-date=2 September 2024}}{{cite web | url = https://ncithesaurus.nci.nih.gov/ncitbrowser/ConceptReport.jsp?dictionary=NCI_Thesaurus&ns=ncit&code=C65417 | title = Dioxifedrine | work = NCI Thesaurus | publisher = U.S. National Cancer Institute | id = Code C65417 }} The drug is a substituted phenethylamine and amphetamine and is the catecholamine (3,4-dihydroxylated) derivative of ephedrine and the amphetamine (α-methylated) analogue of epinephrine (adrenaline). Analogues of dioxifedrine include dioxethedrin (α-methyl-N-ethylnorepinephrine), corbadrine (levonordefrin; α-methylnorepinephrine), and α-methyldopamine.