dimetofrine

{{Short description|Chemical compound}}

{{Drugbox

| Watchedfields = changed

| verifiedrevid = 447927136

| image = Dimetofrine.png

| width = 200px

| tradename = Dovida, Pressamina, Superten

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| class = α₁-Adrenergic receptor agonist; Antihypotensive agent; Vasopressor

| routes_of_administration = Oral

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| CAS_number_Ref = {{cascite|correct|CAS}}

| CAS_number = 22950-29-4

| ATC_prefix = C01

| ATC_suffix = CA12

| PubChem = 31513

| DrugBank_Ref = {{drugbankcite|correct|drugbank}}

| DrugBank = DB13494

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| ChemSpiderID = 29227

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = BOM1J10QQM

| KEGG_Ref = {{keggcite|correct|kegg}}

| KEGG = D07149

| ChEBI = 134932

| ChEMBL = 2105040

| synonyms = Dimethophrine; Dimetrophine; Dimethofrine; DMP; SM-14; 3,5-Dimethoxy-4,β-dihydroxy-N-methylphenethylamine; 3,5-Dimethoxy-4,β-dihydroxy-N-methyl-β-phenylethylamine

| IUPAC_name = (RS)-4-[1-Hydroxy-2-(methylamino)ethyl]-2,6-dimethoxyphenol

| C=11 | H=17 | N=1 | O=4

| SMILES = O(c1cc(cc(OC)c1O)C(O)CNC)C

| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

| StdInChI = 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

| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

| StdInChIKey = ZKGDBJAHIIXDDW-UHFFFAOYSA-N

}}

Dimetofrine ({{Abbrlink|INN|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.{{cite book | last=Elks | first=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=PA443 | access-date=31 August 2024 | page=443}}{{cite book | author=Schweizerischer Apotheker-Verein | title=Index Nominum 2000: International Drug Directory | publisher=Medpharm Scientific Publishers | series=Index nominum | year=2000 | isbn=978-3-88763-075-1 | url=https://books.google.com/books?id=5GpcTQD_L2oC&pg=PA352 | access-date=31 August 2024 | page=352}}{{cite journal |vauthors=Baldrighi V, Aiazzi L, Castelli C, Seveso G |title=Double-blind clinical evaluation of dimetophrine in chronically reduced arterial tension |journal=Curr Med Res Opin |volume=9 |issue=2 |pages=78–85 |year=1984 |pmid=6399891 |doi= 10.1185/03007998409109563}} It is said to be similarly or less effective than midodrine in the treatment of orthostatic hypotension and shows substantially lower potency.{{cite journal | vauthors = McClellan KJ, Wiseman LR, Wilde MI | title = Midodrine. A review of its therapeutic use in the management of orthostatic hypotension | journal = Drugs Aging | volume = 12 | issue = 1 | pages = 76–86 | date = January 1998 | pmid = 9467688 | doi = 10.2165/00002512-199812010-00007 | url = }}{{cite journal | vauthors = McTavish D, Goa KL | title = Midodrine. A review of its pharmacological properties and therapeutic use in orthostatic hypotension and secondary hypotensive disorders | journal = Drugs | volume = 38 | issue = 5 | pages = 757–777 | date = November 1989 | pmid = 2480881 | doi = 10.2165/00003495-198938050-00004 | url = }}

The drug is a selective α₁-adrenergic receptor agonist{{cite journal | vauthors = Marini U, Cecchi A, Venturini M | title = Controlled clinical investigation of dimetophrine versus midodrine in the management of moderately decreased arterial blood pressure | journal = Curr Med Res Opin | volume = 9 | issue = 4 | pages = 265–274 | date = 1984 | pmid = 6210180 | doi = 10.1185/03007998409109590 | url = }} but is also said to have β-adrenergic receptor agonist activity. It is a substituted phenethylamine and is also known as 3,5-dimethoxy-4,β-dihydroxy-N-methylphenethylamine. Its chemical structure is similar to that of desglymidodrine (3,6-dimethoxy-β-hydroxyphenethylamine), the active metabolite of midodrine.

Dimetofrine remained marketed only in Italy in 2000.