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{{Short description|Chemical compound}} |
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{{cs1 config|name-list-style=vanc|display-authors=6}} |
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{{Drugbox |
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{{Drugbox |
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| Verifiedfields = verified |
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| verifiedrevid = 444833048 |
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| Watchedfields = verified |
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| IUPAC_name = (1''R'',2''S'')-''N''-ethyl-''N''-methyl-2-amino-1-phenylpropan-1-ol |
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| verifiedrevid = 449580400 |
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| image = Etafedrine Structural Formulae (1R,2S).png |
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| IUPAC_name = (1''R'',2''S'')-2--1-phenyl-1-propanol |
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| image = Etafedrine.svg |
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| width = 180px |
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<!--Clinical data--> |
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<!-- Clinical data --> |
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| tradename = |
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| tradename = Menetyl; Nethaprin; Novedrin |
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| pregnancy_category = |
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| pregnancy_category = |
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| legal_status = |
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| legal_AU = S2 |
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| legal_BR = D1 |
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| routes_of_administration = |
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| legal_BR_comment = <ref>{{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=] |language=pt-BR |publication-date=2023-04-04}}</ref> |
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| legal_status = Withdrawn from market |
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| routes_of_administration = |
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<!--Pharmacokinetic data--> |
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<!-- Pharmacokinetic data --> |
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| bioavailability = |
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| bioavailability = |
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| metabolism = |
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| metabolism = |
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| elimination_half-life = |
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| elimination_half-life = |
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| excretion = |
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| excretion = |
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<!--Identifiers--> |
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<!-- Identifiers --> |
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| CAS_number_Ref = {{cascite|correct|CAS}} |
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| CAS_number = 7681-79-0 |
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| CAS_number = 48141-64-6 |
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| ATC_prefix = none |
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| ATC_suffix = |
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| ATC_prefix = None |
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| ATC_suffix = |
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| PubChem = 10734 |
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| PubChem = 10734 |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII = 2Y6VQU63E8 |
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| UNII = 2Y6VQU63E8 |
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| DrugBank = DB11587 |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID = 85308 |
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| ChEBI = 134847 |
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| ChEMBL = 2110926 |
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| synonyms = Ethylephedrine; ''N''-Ethylephedrine |
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<!--Chemical data--> |
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<!-- Chemical data --> |
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| C=12 | H=19 | N=1 | O=1 |
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| C=12 | H=19 | N=1 | O=1 |
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| SMILES = O(c1ccccc1)(N(CC)C)C |
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| molecular_weight = 193.285 g/mol |
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| StdInChI_Ref = {{stdinchicite|changed|chemspider}} |
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| 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 |
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| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}} |
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| StdInChIKey = IRVLBORJKFZWMI-JQWIXIFHSA-N |
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}} |
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}} |
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'''Etafedrine''' (]) or '''ethylephedrine''' is a long-acting ] and has the brand name '''Nethaprin'''. It was previously commercially available as both the ] and as the ] ] from ] but is now no longer marketed. |
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'''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 ] used as a ] to treat ].<ref name="Elks2014">{{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}}</ref><ref name="MortonHall2012">{{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}}</ref><ref name="DrugBank">{{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}}</ref> It was previously commercially available as both the ] and as the ] ] from Sanofi-Aventis (now ]) but is now no longer marketed.{{Citation needed|date=August 2024}} |
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== Pharmacology == |
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==Pharmacology== |
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Unlike ] and ], etafedrine does not ] of ] or ] and instead acts as a ] ], thereby mediating its ] effects.<ref name="DrugBank" /><ref name="LindmarLöffelholzStieh=Koch1985">{{cite journal | vauthors = Lindmar R, Löffelholz K, Stieh-Koch U | title = On the mechanism of bronchodilatation by etafedrine | journal = Arzneimittel-Forschung | volume = 35 | issue = 3 | pages = 602–604 | year = 1985 | pmid = 4039586 }}</ref> |
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==See also== |
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Unlike ] and ], etafedrine does not induce the release of ] or ] and instead acts as a ] ] ], thereby mediating its bronchodilator effects.<ref name="pmid4039586">{{cite journal | author = Lindmar R, Löffelholz K, Stieh-Koch U | title = On the mechanism of bronchodilatation by etafedrine | journal = Arzneimittel-Forschung | volume = 35 | issue = 3 | pages = 602–4 | year = 1985 | pmid = 4039586 | doi = | url = }}</ref> |
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* ] |
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* ] |
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== Synthesis == |
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==References== |
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Although there are four possible ] of ethylephedrine, the pharmacological agent is the (1''R'', 2''S'') form. This isomer may be synthesized by ] naturally-occurring ] with ]. The hydrochloride may be prepared by passing ] through a solution of ethylephedrine in ]:<ref>{{cite journal | title = Studies on Syntheses and Pharmacological Effects of N-Alkylephedrines and their Ammonium Salt Derivatives | author = Takeo Ueda,Shigeshi Toyoshima,Kiyoshi Takahashi and Masako Muraoka | journal = ] | volume = 3 | issue = 6 | year = 1955 | pages = 465–468 | url = http://www.journalarchive.jst.go.jp/jnlpdf.php?cdjournal=cpb1953&cdvol=3&noissue=6&startpage=465&lang=en&from=jnltoc | format = Free full text}}</ref> |
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:] |
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== See also == |
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* ] |
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== References == |
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{{Reflist}} |
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{{Reflist}} |
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{{Drugs for obstructive airway diseases}} |
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{{Stimulants}} |
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{{Adrenergic receptor modulators}} |
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{{Adrenergics}} |
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{{Phenethylamines}} |
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{{Phenethylamines}} |
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{{nervous-system-drug-stub}} |
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] |