methoxamine
{{Short description|Chemical compound}}
{{Distinguish|methoxetamine}}
{{Drugbox
| Verifiedfields = verified
| Watchedfields = verified
| verifiedrevid = 422235584
| image = Methoxamine.png
| width = 200px
| tradename = Vasoxine, Vasoxyl, Vasylox, others
| Drugs.com = {{drugs.com|international|methoxamine}}
| pregnancy_AU =
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| routes_of_administration = Oral, injection
| bioavailability =
| protein_bound =
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| elimination_half-life = 3 hours
| excretion = Urine
| CAS_number_Ref = {{cascite|correct|CAS}}
| CAS_number = 390-28-3
| ATC_prefix = C01
| ATC_suffix = CA10
| PubChem = 6082
| IUPHAR_ligand = 483
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| DrugBank = DB00723
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 5857
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = HUQ1KC1YLI
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = D08201
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 524
| synonyms = Methoxamedrine; 2,6-Dimethoxy-β-hydroxy-α-methylphenethylamine; 2,6-Dimethoxy-β-hydroxyamphetamine
| IUPAC_name = 2-amino-1-(2,5-dimethoxyphenyl)propan-1-ol
| C=11 | H=17 | N=1 | O=3
| SMILES = O(c1ccc(OC)cc1C(O)C(N)C)C
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C11H17NO3/c1-7(12)11(13)9-6-8(14-2)4-5-10(9)15-3/h4-7,11,13H,12H2,1-3H3
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = WJAJPNHVVFWKKL-UHFFFAOYSA-N
}}
Methoxamine, sold under the brand names Vasoxine, Vasoxyl, and Vasylox among others, is a sympathomimetic medication used as an antihypotensive agent.{{cite journal | vauthors = Thiele RH, Nemergut EC, Lynch C | title = The physiologic implications of isolated alpha(1) adrenergic stimulation | journal = Anesth Analg | volume = 113 | issue = 2 | pages = 284–296 | date = August 2011 | pmid = 21519050 | doi = 10.1213/ANE.0b013e3182124c0e | url = }}{{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=PA788 | access-date=2024-09-01 | page=788}}{{cite book | vauthors = Pazdernik TL, Kerecsen L | veditors = Goljan EF |title=Pharmacology |edition=Second |series=Rapid Review |year=2007 |orig-year=2003|publisher=Mosby-Elsevier |location=Philadelphia, PA |isbn=978-0-323-04550-6 |page=39 |chapter=5 }} It has mostly or entirely been discontinued.
The drug is an α1-adrenergic receptor agonist.{{Additional citation needed|date=August 2024}}
Medical uses
The long duration of action of methoxamine has been said to have rendered it obsolete in modern clinical practice.
Pharmacology
Methoxamine is an α1-adrenergic receptor agonist. It is described as a long-acting α1-adrenergic receptor agonist and this is contrasted with phenylephrine which is said to be short-acting. Phenylephrine is 5 to 10{{nbsp}}times more potent than methoxamine and has a 3-fold higher maximal effect.
Chemistry
Methoxamine, also known as 2,6-dimethoxy-β-hydroxy-α-methylphenethylamine or as 2,6-dimethoxy-β-hydroxyamphetamine, is a substituted phenethylamine and amphetamine derivative.
It is somewhat similar in chemical structure to those of desglymidodrine (3,6-dimethoxy-β-hydroxyphenethylamine), dimetofrine (3,5-dimethoxy-4,β-dihydroxy-N-methylphenethylamine), 2,5-dimethoxyamphetamine (2,5-DMA), and butaxamine ((1S,2S)-3,6-dimethoxy-β-hydroxy-N-tert-butylamphetamine).
History
Methoxamine was synthesized by 1944. It was marketed in the United States by 1949.
Society and culture
=Names=
Methoxamine is the generic name of the drug and its {{Abbrlink|INN|International Nonproprietary Name}} and {{Abbrlink|BAN|British Approved Name}}, while méthoxamine is its {{Abbrlink|DCF|Dénomination Commune Française}} and methoxamina is its {{Abbrlink|DCIT|Denominazione Comune Italiana}}.{{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&pg=PA669 | access-date=2024-09-01 | page=669}} In the case of the hydrochloride salt, its generic name is methoxamine hydrochloride and this is its {{Abbrlink|USAN|United States Adopted Name}}, {{Abbrlink|BANM|British Approved Name}}, and {{Abbrlink|JAN|Japanese Accepted Name}}. A synonym of methoxamine is methoxamedrine. The drug has been sold under brand names including Idasal, Mexan, Pressomin, Vasosterol, Vasoxine, Vasoxyl, and Vasylox.
=Availability=
Methoxamine has been marketed in Canada, the Czech Republic, Ireland, Japan, Spain, the United Kingdom, and the United States and was available in these countries in 2000.{{cite web | title=Methoxamine | date=20 October 2012 | url=https://drugs.com/international/methoxamine.html | archive-url=https://web.archive.org/web/20160303224546/https://drugs.com/international/methoxamine.html | archive-date=3 March 2016 | url-status=unfit | access-date=1 September 2024}} However, it was discontinued in Canada and the United Kingdom by 2004.{{cite book | author=Schweizerischer Apotheker-Verein | title=Index Nominum: International Drug Directory | publisher=Medpharm Scientific Publishers | year=2004 | isbn=978-3-88763-101-7 | url=https://books.google.com/books?id=EgeuA47Ocm4C&pg=PA779 | access-date=1 September 2024 | page=779}} It has also been discontinued in the United States.{{cite web | title=Drugs@FDA: FDA-Approved Drugs | website=accessdata.fda.gov | url=https://www.accessdata.fda.gov/scripts/cder/daf/index.cfm?event=overview.process&varApplNo=006772 | access-date=1 September 2024}} By 2016, methoxamine appeared to remain available only in Japan.
References
{{Reflist}}
{{Stimulants}}
{{Cardiac stimulants excluding cardiac glycosides}}
{{Decongestants}}
{{Adrenergic receptor modulators}}
{{Phenethylamines}}
Category:Alpha-1 adrenergic receptor agonists
Category:Antihypotensive agents
Category:Beta-Hydroxyamphetamines