Dimetofrine

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
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 ;
PubChem CID	31513;
DrugBank	DB13494 ;
ChemSpider	29227 ;
UNII	BOM1J10QQM;
KEGG	D07149 ;
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 ; Key:ZKGDBJAHIIXDDW-UHFFFAOYSA-N ;
	(verify)

Dimetofrine (INNTooltip International Nonproprietary Name), also known as dimethophrine or dimetophrine and sold under the brand names Dovida, Pressamina, and Superten, is a medication described as a sympathomimetic, vasoconstrictor, and cardiac stimulant.^[2]^[3]^[4] It is said to be similarly or less effective than midodrine in the treatment of orthostatic hypotension and shows substantially lower potency.^[5]^[1]

The drug is a selective α₁-adrenergic receptor agonist^[6] but is also said to have β-adrenergic receptor agonist activity.^[1] It is a substituted phenethylamine and is also known as 3,5-dimethoxy-4,β-dihydroxy-N-methylphenethylamine.^[2] Its chemical structure is similar to that of desglymidodrine (3,6-dimethoxy-β-hydroxyphenethylamine), the active metabolite of midodrine.^[5]

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

References

^ ^a ^b ^c McTavish 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 ^b Elks, J. (2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer US. p. 443. ISBN 978-1-4757-2085-3. Retrieved 31 August 2024.
^ ^a ^b Schweizerischer Apotheker-Verein (2000). Index Nominum 2000: International Drug Directory. Index nominum. Medpharm Scientific Publishers. p. 352. ISBN 978-3-88763-075-1. Retrieved 31 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 ^b McClellan 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.

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[McTavishGoa1989-1] McTavish 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.

[Elks2014-2] Elks, J. (2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer US. p. 443. ISBN 978-1-4757-2085-3. Retrieved 31 August 2024.

[IndexNominum2000-3] Schweizerischer Apotheker-Verein (2000). Index Nominum 2000: International Drug Directory. Index nominum. Medpharm Scientific Publishers. p. 352. ISBN 978-3-88763-075-1. Retrieved 31 August 2024.

[BaldrighiAiazziCastelli1984-4] 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.

[McClellanWisemanWilde1998-5] McClellan 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.

[MariniCecchiVenturini1984-6] 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.

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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-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-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: BOH 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 (also D-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
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