Dextrofemine

Dextrofemine
Clinical data
Trade names	Marsyl, Dysmalgine
Other names	(+)-N-(1-Methyl-2-phenoxyethyl)amphetamine; CB-3697; Dextrophemine
Drug class	β-Adrenergic receptor agonist; Tocolytic
Identifiers
	IUPAC name N-(1-phenoxypropan-2-yl)-1-phenylpropan-2-amine;
CAS Number	15687-08-8;
PubChem CID	71879;
ChemSpider	32699672;
UNII	WVB6I50566;
ChEBI	CHEBI:135109;
ChEMBL	ChEMBL2106250;
CompTox Dashboard (EPA)	DTXSID901043133 ;
Chemical and physical data
Formula	C18H23NO
Molar mass	269.388 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CC(CC1=CC=CC=C1)NC(C)COC2=CC=CC=C2;
	InChI InChI=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; Key:URCIJDUOBBSMII-UHFFFAOYSA-N;

Dextrofemine (INNTooltip International Nonproprietary Name), sold under the brand names Marsyl and Dysmalgine, is a uterine spasmolytic and muscle relaxant of the amphetamine family.^[1]^[2]^[3]^[4]^[5] It is the dextrorotatory enantiomer of racefemine.^[1]^[2] The drug acts as a β-adrenergic receptor agonist and sympathomimetic.^[6] It was marketed in France in 1966 but appears to no longer be marketed.^[3]^[7]^[8] Other tocolytics with similar chemical structures as phenethylamines or amphetamines include bedoradrine, buphenine, fenoterol, hexoprenaline, isoxsuprine, ritodrine, and terbutaline.^[6]^[1]

References

^ ^a ^b ^c Elks J (2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer US. pp. 804, others. ISBN 978-1-4757-2085-3. Retrieved 9 October 2024.
^ ^a ^b Martindale W, Reynolds JE (1993). The Extra Pharmacopoeia. Martindale Series. Pharmaceutical Press. p. 1408. ISBN 978-0-85369-300-0. Retrieved 9 October 2024. Racefemine fumarate has been used as a uterine relaxant. The dextrorotatory isomer, dextrofemine, has been used intravenously.
^ ^a ^b Schlesser JL (1990). Drugs Available Abroad: A Guide to Therapeutic Drugs Available and Approved for Use Outside the U. S. Gale Research, Derwent Publications Inc. p. 61. ISBN 978-0-8103-7177-4. Retrieved 9 October 2024. 268. Dextrofemine. Countries Where Available and Release Dates: France (1966). Brand Names and Manufactgurers: Base: Dysmalgine—Clin-Midy (France). Drug Action: Spasmolytic; uterine relaxant.
^ Negwer M (1994). Organic-chemical Drugs and Their Synonyms: (an International Survey). Akad.-Verlag. p. 1470. ISBN 978-3-05-500156-7. Retrieved 9 October 2024. Dextrofemine, Dysmalgine injectable , Marsyl U Uterine spasmolytic , muscle relaxant
^ de Rochambeau B, Mellier G, Dargent D (1990). "[Doppler umbilical artery velocimetry during labor in normal pregnancies]". J Gynecol Obstet Biol Reprod (Paris) (in French). 19 (1): 48–52. PMID 2313067.
^ ^a ^b Sas M, Kovács L (1981). "Systemic Pharmacology of Adrenergic Activators and Inhibitors: Effects on the Genital System". Handbook of Experimental Pharmacology. Vol. 54 / 2. Berlin, Heidelberg: Springer Berlin Heidelberg. pp. 213–242. doi:10.1007/978-3-642-67584-3_5. ISBN 978-3-642-67586-7. ISSN 0171-2004.
^ Muller NF, Dessing RP (1997). European Drug Index: European Drug Registrations, Fourth Edition (in Danish). Taylor & Francis. p. 412. ISBN 978-1-351-44947-2. Retrieved 9 October 2024.
^ Schweizerischer Apotheker-Verein (2000). Index Nominum 2000: International Drug Directory. Medpharm Scientific Publishers. ISBN 978-3-88763-075-1. Retrieved 9 October 2024.

[Elks2014-1] Elks J (2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer US. pp. 804, others. ISBN 978-1-4757-2085-3. Retrieved 9 October 2024.

[MartindaleReynolds1993-2] Martindale W, Reynolds JE (1993). The Extra Pharmacopoeia. Martindale Series. Pharmaceutical Press. p. 1408. ISBN 978-0-85369-300-0. Retrieved 9 October 2024. Racefemine fumarate has been used as a uterine relaxant. The dextrorotatory isomer, dextrofemine, has been used intravenously.

[Schlesser1990-3] Schlesser JL (1990). Drugs Available Abroad: A Guide to Therapeutic Drugs Available and Approved for Use Outside the U. S. Gale Research, Derwent Publications Inc. p. 61. ISBN 978-0-8103-7177-4. Retrieved 9 October 2024. 268. Dextrofemine. Countries Where Available and Release Dates: France (1966). Brand Names and Manufactgurers: Base: Dysmalgine—Clin-Midy (France). Drug Action: Spasmolytic; uterine relaxant.

[Negwer1994-4] Negwer M (1994). Organic-chemical Drugs and Their Synonyms: (an International Survey). Akad.-Verlag. p. 1470. ISBN 978-3-05-500156-7. Retrieved 9 October 2024. Dextrofemine, Dysmalgine injectable , Marsyl U Uterine spasmolytic , muscle relaxant

[deRochambeauMellierDargent1990-5] Rochambeau B, Mellier G, Dargent D (1990). "[Doppler umbilical artery velocimetry during labor in normal pregnancies]". J Gynecol Obstet Biol Reprod (Paris) (in French). 19 (1): 48–52. PMID 2313067.

[SasKovács1981-6] Sas M, Kovács L (1981). "Systemic Pharmacology of Adrenergic Activators and Inhibitors: Effects on the Genital System". Handbook of Experimental Pharmacology. Vol. 54 / 2. Berlin, Heidelberg: Springer Berlin Heidelberg. pp. 213–242. doi:10.1007/978-3-642-67584-3_5. ISBN 978-3-642-67586-7. ISSN 0171-2004.

[MullerDessing1997-7] Muller NF, Dessing RP (1997). European Drug Index: European Drug Registrations, Fourth Edition (in Danish). Taylor & Francis. p. 412. ISBN 978-1-351-44947-2. Retrieved 9 October 2024.

[IndexNominum2000-8] Schweizerischer Apotheker-Verein (2000). Index Nominum 2000: International Drug Directory. Medpharm Scientific Publishers. ISBN 978-3-88763-075-1. Retrieved 9 October 2024.

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