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Dimetofrine

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Chemical compound

Pharmaceutical compound

Dimetofrine
Clinical data

Trade names	Dovida, Pressamina, Superten
Other names	Dimethophrine; Dimetrophine; Dimethofrine; DMP; SM-14; 3,5-Dimethoxy-4,β-dihydroxy-N-methylphenethylamine; 3,5-Dimethoxy-4,β-dihydroxy-N-methyl-β-phenylethylamine
Routes of administration	Oral^[1]
Drug class	α₁-Adrenergic receptor agonist;Antihypotensive agent;Vasopressor
ATC code	C01CA12 (WHO)
Identifiers
IUPAC name (RS)-4-[1-Hydroxy-2-(methylamino)ethyl]-2,6-dimethoxyphenol
CAS Number	22950-29-4^Y
PubChemCID	31513
DrugBank	DB13494^Y
ChemSpider	29227^Y
UNII	BOM1J10QQM
KEGG	D07149^Y
ChEBI	CHEBI:134932
ChEMBL	ChEMBL2105040
CompTox Dashboard(EPA)	DTXSID60865076
ECHA InfoCard	100.041.210
Chemical and physical data
Formula	C₁₁H₁₇NO₄
Molar mass	227.260 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES O(c1cc(cc(OC)c1O)C(O)CNC)C
InChI InChI=1S/C11H17NO4/c1-12-6-8(13)7-4-9(15-2)11(14)10(5-7)16-3/h4-5,8,12-14H,6H2,1-3H3^Y Key:ZKGDBJAHIIXDDW-UHFFFAOYSA-N^Y
(verify)

Dimetofrine (INNTooltip International Nonproprietary Name), also known asdimethophrine ordimetophrine and sold under the brand namesDovida,Pressamina, andSuperten, is amedication described as asympathomimetic,vasoconstrictor, andcardiac stimulant.^[2]^[3]^[4] It is said to be similarly or less effective thanmidodrine in the treatment oforthostatic hypotension and shows substantially lowerpotency.^[5]^[1]

The drug is aselective α₁-adrenergic receptor agonist^[6] but is also said to haveβ-adrenergic receptor agonist activity.^[1] It is asubstituted phenethylamine and is also known as 3,5-dimethoxy-4,β-dihydroxy-N-methylphenethylamine.^[2] Itschemical structure is similar to that ofdesglymidodrine (3,6-dimethoxy-β-hydroxyphenethylamine), theactive metabolite of midodrine.^[5]

Dimetofrine remained marketed only inItaly in 2000.^[3]

References

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^^a ^b ^cMcTavish D, Goa KL (November 1989). "Midodrine. A review of its pharmacological properties and therapeutic use in orthostatic hypotension and secondary hypotensive disorders".Drugs.38 (5):757–777.doi:10.2165/00003495-198938050-00004.PMID 2480881.
^^a ^bElks, J. (2014).The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer US. p. 443.ISBN 978-1-4757-2085-3. Retrieved31 August 2024.
^^a ^bSchweizerischer Apotheker-Verein (2000).Index Nominum 2000: International Drug Directory. Index nominum. Medpharm Scientific Publishers. p. 352.ISBN 978-3-88763-075-1. Retrieved31 August 2024.
^Baldrighi V, Aiazzi L, Castelli C, Seveso G (1984). "Double-blind clinical evaluation of dimetophrine in chronically reduced arterial tension".Curr Med Res Opin.9 (2):78–85.doi:10.1185/03007998409109563.PMID 6399891.
^^a ^bMcClellan KJ, Wiseman LR, Wilde MI (January 1998). "Midodrine. A review of its therapeutic use in the management of orthostatic hypotension".Drugs Aging.12 (1):76–86.doi:10.2165/00002512-199812010-00007.PMID 9467688.
^Marini U, Cecchi A, Venturini M (1984). "Controlled clinical investigation of dimetophrine versus midodrine in the management of moderately decreased arterial blood pressure".Curr Med Res Opin.9 (4):265–274.doi:10.1185/03007998409109590.PMID 6210180.

Cardiac stimulants excluding cardiac glycosides (C01C)

Adrenergic and
dopaminergic agents

Adrenergic agonists

α	Denopamine Metaraminol Methoxamine Midodrine Norfenefrine Oxedrine Phenylephrine
β	Arbutamine Dobutamine Isoprenaline Prenalterol
mixed	Amezinium metilsulfate Droxidopa Epinephrine # Etilefrine Norepinephrine

Dopamine agonists

Fenoldopam

Both

Unknown/ungrouped

Phosphodiesterase inhibitors (PDE3I)

Other cardiac stimulants

^#WHO-EM
^‡Withdrawn from market
Clinical trials:
- ^†Phase III
- ^§Never to phase III

Adrenergic receptor modulators

α₁

Agonists

Antagonists

α₂

Agonists

Antagonists

Agonists

Antagonists

See also:Receptor/signaling modulators
Dopaminergics
Serotonergics
Monoamine reuptake inhibitors
Monoamine releasing agents
Monoamine metabolism modulators
Monoamine neurotoxins

v t e Phenethylamines
Phenethylamines	Psychedelics:25B-NBOMe 25C-NBOMe 25D-NBOMe 25I-NBOMe 25N-NBOMe 2C-B 2C-B-AN 2C-Bn 2C-Bu 2C-C 2C-CN 2C-CP 2C-D 2C-E 2C-EF 2C-F 2C-G 2C-G-1 2C-G-2 2C-G-3 2C-G-4 2C-G-5 2C-G-6 2C-G-N 2C-H 2C-I 2C-iBu 2C-iP 2C-N 2C-NH2 2C-O 2C-O-4 2C-P 2C-Ph 2C-SE 2C-T 2C-T-2 2C-T-3 2C-T-4 2C-T-5 2C-T-6 2C-T-7 2C-T-8 2C-T-9 2C-T-10 2C-T-11 2C-T-12 2C-T-13 2C-T-14 2C-T-15 2C-T-16 2C-T-17 2C-T-18 2C-T-19 2C-T-20 2C-T-21 2C-T-22 2C-T-22.5 2C-T-23 2C-T-24 2C-T-25 2C-T-27 2C-T-28 2C-T-30 2C-T-31 2C-T-32 2C-T-33 2C-tBu 2C-TFE 2C-TFM 2C-YN 2C-V Allylescaline DESOXY Escaline Isoproscaline Jimscaline Macromerine MEPEA Mescaline Metaescaline Methallylescaline Proscaline Psi-2C-T-4 TCB-2 Stimulants:Phenylethanolamine Hordenine Phenethylamine Phenpromethamine α-Methylphenethylamine (amphetamine) β-Methylphenethylamine m-Methylphenethylamine N-Methylphenethylamine o-Methylphenethylamine p-Methylphenethylamine Methylphenidate Entactogens:Lophophine MDPEA MDMPEA Others:Biscaline BOH Buscaline DMPEA
Amphetamines	Psychedelics:3C-AL 3C-BZ 3C-E 3C-MAL 3C-P Aleph Beatrice Bromo-DragonFLY D-Deprenyl DMA DMCPA DMMDA DOB DOC DOEF DOET DOI DOM DON DOPR DOTFM Ganesha MMDA MMDA-2 Psi-DOM TMA TeMA ZDCM-04 Stimulants:2-FA 2-FMA 3-FA 3-FMA Acridorex Alfetamine Amfecloral Amfepentorex Amphetamine (Dextroamphetamine,Levoamphetamine) Amphetaminil Benfluorex Benzphetamine Cathine Clobenzorex Dimethylamphetamine Ephedrine Etilamfetamine Fencamfamin Fencamine Fenethylline Fenfluramine (Dexfenfluramine,Levofenfluramine) Fenproporex Flucetorex Fludorex Formetorex Furfenorex Gepefrine 4-Hydroxyamphetamine Iofetamine Isopropylamphetamine Lefetamine Lisdexamfetamine Mefenorex Metaraminol Methamphetamine (Dextromethamphetamine,Levomethamphetamine) Methoxyphenamine MMA Morforex Norfenfluramine L-Norpseudoephedrine N,alpha-Diethylphenylethylamine Oxifentorex Oxilofrine Ortetamine PBA PCA PFA PFMA PIA PMA PMEA PMMA Phenylpropanolamine Pholedrine Prenylamine Propylamphetamine Pseudoephedrine Sibutramine Tiflorex Tranylcypromine Xylopropamine Zylofuramine Entactogens:4-FA 4-FMA 4-MA 4-MMA 4-MTA 5-APB 5-APDB 5-EAPB 5-IT 5-MAPB 5-MAPDB 6-APB 6-APDB 6-Chloro-MDMA 6-EAPB 6-IT 6-MAPB 6-MAPDB EDA IAP 2,3-MDA 3,4-MDA (tenamfetamine) MDEA MDHMA MDMA (midomafetamine) MDOH Methamnetamine MMDMA Naphthylaminopropane TAP Others:3,4-DCA Amiflamine DiFMDA Selegiline (alsoD-Deprenyl)
Phentermines	Stimulants:Chlorphentermine Cloforex Clortermine Etolorex Mephentermine Pentorex Phentermine Entactogens:MDPH MDMPH Others:Cericlamine
Cathinones	Stimulants:3-FMC 4-MC 4-BMC 4-CMC 4-EMC 4-FMC 4-MEC 4-MeMABP 4-MPD Amfepramone Benzedrone Brephedrone Buphedrone Bupropion Cathinone Dimethylcathinone Ethcathinone Eutylone Hydroxybupropion Methcathinone Methedrone NEB N-Ethylhexedrone N-Ethylpentedrone Pentedrone Pentylone Radafaxine Entactogens:3,4-DMMC 3-MMC Butylone Ethylone Methylone Methylenedioxycathinone Mephedrone Propylone
Phenylisobutylamines	Entactogens:4-CAB 4-MAB Ariadne BDB Butylone EBDB Eutylone MBDB Stimulants:Phenylisobutylamine
Phenylalkylpyrrolidines	Stimulants:α-PBP α-PHP α-PPP α-PVP MDPBP MDPPP MDPV 4-MePBP 4-MePHP 4-MePPP MOPPP MOPVP MPBP MPHP MPPP Naphyrone PEP Prolintane Pyrovalerone
Catecholamines (and close relatives)	6-FNE 6-OHDA a-Me-DA a-Me-TRA Adrenochrome Ciladopa D-DOPA (Dextrodopa) Dimetofrine Dopamine Epinephrine Epinine Etilefrine Ethylnorepinephrine Fenclonine Ibopamine Isoprenaline Isoetarine L-DOPA (Levodopa) L-DOPS (Droxidopa) L-Phenylalanine L-Tyrosine m-Tyramine Metanephrine Metaraminol Metaterol Metirosine Methyldopa N,N-Dimethyldopamine Nordefrin (Levonordefrin) Norepinephrine Norfenefrine (m-Octopamine) Normetanephrine Orciprenaline p-Octopamine p-Tyramine Phenylephrine Synephrine
Miscellaneous	AL-LAD Amidephrine Arbutamine Cafedrine Denopamine Desvenlafaxine Diphenidine Dizocilpine Dobutamine Dopexamine Ephenidine Etafedrine ETH-LAD Famprofazone Fluorolintane Hexapradol IP-LAD Lysergic acid amide Lysergic acid 2-butyl amide Lysergic acid 2,4-dimethylazetidide Lysergic acid diethylamide Methoxamine Methoxphenidine MT-45 PARGY-LAD Phenibut PRO-LAD Pronethalol Salbutamol (Levosalbutamol) Solriamfetol Theodrenaline Thiamphenicol UWA-101 Venlafaxine

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