dextrofemine

{{Short description|Tocolytic}}

{{Cs1 config|name-list-style=vanc|display-authors=6}}

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| image = Dextrofemine.svg

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| tradename = Marsyl, Dysmalgine

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| class = β-Adrenergic receptor agonist; Tocolytic

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| CAS_number = 15687-08-8

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| PubChem = 71879

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| ChemSpiderID = 32699672

| UNII = WVB6I50566

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| ChEBI = 135109

| ChEMBL = 2106250

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| synonyms = (+)-N-(1-Methyl-2-phenoxyethyl)amphetamine; CB-3697; Dextrophemine

| IUPAC_name = N-(1-phenoxypropan-2-yl)-1-phenylpropan-2-amine

| C=18 | H=23 | N=1 | O=1

| SMILES = CC(CC1=CC=CC=C1)NC(C)COC2=CC=CC=C2

| StdInChI = 1S/C18H23NO/c1-15(13-17-9-5-3-6-10-17)19-16(2)14-20-18-11-7-4-8-12-18/h3-12,15-16,19H,13-14H2,1-2H3

| StdInChIKey = URCIJDUOBBSMII-UHFFFAOYSA-N

}}

Dextrofemine ({{Abbrlink|INN|International Nonproprietary Name}}), sold under the brand names Marsyl and Dysmalgine, is a uterine spasmolytic and muscle relaxant of the amphetamine family.{{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=PA804 | access-date=9 October 2024 | pages=804, others}}{{cite book | vauthors = Martindale W, Reynolds JE | title=The Extra Pharmacopoeia | publisher=Pharmaceutical Press | series=Martindale Series | year=1993 | isbn=978-0-85369-300-0 | url=https://books.google.com/books?id=EGZWAAAAYAAJ | access-date=9 October 2024 | page=1408 | quote=Racefemine fumarate has been used as a uterine relaxant. The dextrorotatory isomer, dextrofemine, has been used intravenously.}}{{cite book | vauthors = Schlesser JL | title=Drugs Available Abroad: A Guide to Therapeutic Drugs Available and Approved for Use Outside the U. S. | publisher=Gale Research, Derwent Publications Inc. | year=1990 | isbn=978-0-8103-7177-4 | url=https://books.google.com/books?id=2x1tAAAAMAAJ | access-date=9 October 2024 | page=61 | quote=268. Dextrofemine. Countries Where Available and Release Dates: France (1966). Brand Names and Manufactgurers: Base: Dysmalgine—Clin-Midy (France). Drug Action: Spasmolytic; uterine relaxant.}}{{cite book | vauthors = Negwer M | title=Organic-chemical Drugs and Their Synonyms: (an International Survey) | publisher=Akad.-Verlag | year=1994 | isbn=978-3-05-500156-7 | url=https://books.google.com/books?id=SwltAAAAMAAJ | access-date=9 October 2024 | page=1470 | quote=Dextrofemine, Dysmalgine injectable , Marsyl U Uterine spasmolytic , muscle relaxant}}{{cite journal | vauthors = de Rochambeau B, Mellier G, Dargent D | title = [Doppler umbilical artery velocimetry during labor in normal pregnancies] | language = French | journal = J Gynecol Obstet Biol Reprod (Paris) | volume = 19 | issue = 1 | pages = 48–52 | date = 1990 | pmid = 2313067 | doi = | url = }} It is the dextrorotatory enantiomer of racefemine. The drug acts as a β-adrenergic receptor agonist and sympathomimetic.{{cite book | vauthors = Sas M, Kovács L | title=Handbook of Experimental Pharmacology | chapter=Systemic Pharmacology of Adrenergic Activators and Inhibitors: Effects on the Genital System | publisher=Springer Berlin Heidelberg | publication-place=Berlin, Heidelberg | year=1981 | volume=54 / 2 | isbn=978-3-642-67586-7 | issn=0171-2004 | doi=10.1007/978-3-642-67584-3_5 | pages=213–242}} It was marketed in France in 1966 but appears to no longer be marketed.{{cite book | vauthors = Muller NF, Dessing RP | title=European Drug Index: European Drug Registrations, Fourth Edition | publisher=Taylor & Francis | year=1997 | isbn=978-1-351-44947-2 | url=https://books.google.com/books?id=GCBiEAAAQBAJ&pg=PA412 | language=da | access-date=9 October 2024 | page=412}}{{cite book | author=Schweizerischer Apotheker-Verein | title=Index Nominum 2000: International Drug Directory | publisher=Medpharm Scientific Publishers | year=2000 | isbn=978-3-88763-075-1 | url=https://books.google.com/books?id=5GpcTQD_L2oC | access-date=9 October 2024 | page=}} Other tocolytics with similar chemical structures as phenethylamines or amphetamines include bedoradrine, buphenine, fenoterol, hexoprenaline, isoxsuprine, ritodrine, and terbutaline.