:Metaterol

{{Short description|Chemical compound}}

{{Drugbox

| image = Metaterol.svg

| width = 200px

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| CAS_number = 3571-71-9

| ATC_prefix = None

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| PubChem = 19136

| ChemSpiderID = 18056

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = KBU4V9QUHY

| synonyms = Isofenefrine; Isopropylnoradrianol; 3,β-Dihydroxy-N-isopropylphenethylamine

| IUPAC_name = 3-[1-hydroxy-2-(propan-2-ylamino)ethyl]phenol

| C=11 | H=17 | N=1 | O=2

| SMILES = OC(c1cc(O)ccc1)CNC(C)C

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Metaterol ({{Abbrlink|INN|International Nonproprietary Name}}), also known as isofenefrine, isopropylnoradrianol, and 3,β-dihydroxy-N-isopropylphenethylamine, is a sympathomimetic and bronchodilator of the phenethylamine family that was never marketed.{{cite book | last=Elks | first=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=PA777 | access-date=1 September 2024 | page=777}}{{cite book | vauthors = Triggle DJ | title = Dictionary of Pharmacological Agents | publisher = Chapman & Hall/CRC | location = Boca Raton | year = 1996 | isbn = 0-412-46630-9 | url = https://books.google.com/books?id=Z_mfTTIApVEC}}{{cite book | last=Negwer | first=M. | title=Organic-chemical Drugs and Their Synonyms: (an International Survey) | publisher=Akademie Verlag | year=1994 | isbn=978-3-05-500156-7 | url=https://books.google.com/books?id=1ghtAAAAMAAJ&pg=PA573 | access-date=1 September 2024 | page=573 | quote = [...] S Isofenefrine, Metaterol**, S 40045-9 U Sympathomimetic, broncholytic}}{{cite journal | vauthors = Gilson M, Dresse A, Lecomte J | title = On some pharmacodynamic properties of isopropylnoradrianol| language = French | journal = Comptes Rendus des Séances de la Société de Biologie et de Ses Filiales| volume = 155 | issue = | pages = 1715–1718 | date = 1961 | pmid = 13898708 | doi = | url = }} It is structurally related to norfenefrine, phenylephrine, and etilefrine.