etafedrine

{{Short description|Chemical compound}}

{{cs1 config|name-list-style=vanc|display-authors=6}}

{{Drugbox

| Verifiedfields = verified

| Watchedfields = verified

| verifiedrevid = 449580400

| IUPAC_name = (1R,2S)-2-[Ethyl(methyl)amino]-1-phenyl-1-propanol

| image = Etafedrine.svg

| width = 180px

| tradename = Menetyl; Nethaprin; Novedrin

| pregnancy_category =

| legal_AU = S2

| legal_BR = D1

| legal_BR_comment = {{Cite web |author=Anvisa |author-link=Brazilian Health Regulatory Agency |date=2023-03-31 |title=RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial |trans-title=Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control|url=https://www.in.gov.br/en/web/dou/-/resolucao-rdc-n-784-de-31-de-marco-de-2023-474904992 |url-status=live |archive-url=https://web.archive.org/web/20230803143925/https://www.in.gov.br/en/web/dou/-/resolucao-rdc-n-784-de-31-de-marco-de-2023-474904992 |archive-date=2023-08-03 |access-date=2023-08-15 |publisher=Diário Oficial da União |language=pt-BR |publication-date=2023-04-04}}

| legal_status = Withdrawn from market

| routes_of_administration =

| bioavailability =

| metabolism =

| elimination_half-life =

| excretion =

| CAS_number_Ref = {{cascite|correct|CAS}}

| CAS_number = 48141-64-6

| ATC_prefix = None

| ATC_suffix =

| PubChem = 10734

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

| UNII = 2Y6VQU63E8

| DrugBank = DB11587

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| ChemSpiderID = 85308

| ChEBI = 134847

| ChEMBL = 2110926

| synonyms = Ethylephedrine; N-Ethylephedrine

| C=12 | H=19 | N=1 | O=1

| SMILES = O[C@H](c1ccccc1)[C@@H](N(CC)C)C

| StdInChI_Ref = {{stdinchicite|changed|chemspider}}

| StdInChI = 1S/C12H19NO/c1-4-13(3)10(2)12(14)11-8-6-5-7-9-11/h5-10,12,14H,4H2,1-3H3/t10-,12-/m0/s1

| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}

| StdInChIKey = IRVLBORJKFZWMI-JQWIXIFHSA-N

}}

Etafedrine ({{Abbrlink|INN|International Nonproprietary Name}}, {{Abbrlink|BAN|British Approved Name}}), sold under the brand name Nethaprin among others and also known as N-ethylephedrine, is a sympathomimetic agent used as a bronchodilator to treat asthma.{{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=PA503 | access-date=30 August 2024 | page=503}}{{cite book | vauthors = Morton IK, Hall JM | title=Concise Dictionary of Pharmacological Agents: Properties and Synonyms | publisher=Springer Netherlands | year=2012 | isbn=978-94-011-4439-1 | url=https://books.google.com/books?id=tsjrCAAAQBAJ&pg=PA114 | access-date=30 August 2024 | page=114}}{{cite web | title=Etafedrine: Uses, Interactions, Mechanism of Action | website=DrugBank Online | date=31 December 1983 | url=https://go.drugbank.com/drugs/DB11587 | access-date=30 August 2024}} It was previously commercially available as both the free base and as the hydrochloride salt from Sanofi-Aventis (now Sanofi) but is now no longer marketed.{{Citation needed|date=August 2024}}