Methoxamine
Chemical compound
From Wikipedia, the free encyclopedia
Methoxamine, sold under the brand names Vasoxine, Vasoxyl, and Vasylox among others, is a sympathomimetic medication used as an antihypotensive agent.[2][3][4][5] It has mostly or entirely been discontinued.[6]
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| Clinical data | |
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| Trade names | Vasoxine, Vasoxyl, Vasylox, others |
| Other names | Methoxamedrine; 2,5-Dimethoxy-β-hydroxy-α-methylphenethylamine; 2,5-Dimethoxy-β-hydroxyamphetamine; β-Hydroxy-2,5-DMA; β-Hydroxy-DMA; β-Hydroxy-DOH |
| AHFS/Drugs.com | International Drug Names |
| Routes of administration | Oral, injection[1] |
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| Pharmacokinetic data | |
| Elimination half-life | 3 hours |
| Excretion | Urine |
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| CompTox Dashboard (EPA) | |
| ECHA InfoCard | 100.006.244 |
| Chemical and physical data | |
| Formula | C11H17NO3 |
| Molar mass | 211.261 g·mol−1 |
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The drug is an α1-adrenergic receptor agonist.[4][additional citation(s) needed]
Medical uses
The long duration of action of methoxamine has been said to have rendered it obsolete in modern clinical practice.[2]
Pharmacology
Methoxamine is an α1-adrenergic receptor agonist.[2] It is described as a long-acting α1-adrenergic receptor agonist and this is contrasted with phenylephrine which is said to be short-acting.[2] Phenylephrine is 5 to 10 times more potent than methoxamine and has a 3-fold higher maximal effect.[2]
Chemistry
Methoxamine, also known as 2,5-dimethoxy-β-hydroxy-α-methylphenethylamine or as 2,5-dimethoxy-β-hydroxyamphetamine, is a substituted phenethylamine and amphetamine derivative.[3]
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.[3] It was marketed in the United States by 1949.[1]
Society and culture
Names
Methoxamine is the generic name of the drug and its INN and BAN, while méthoxamine is its DCF and methoxamina is its DCIT.[3][4][6] In the case of the hydrochloride salt, its generic name is methoxamine hydrochloride and this is its USAN, BANM, and JAN.[3][4][7][6] A synonym of methoxamine is methoxamedrine.[4] The drug has been sold under brand names including Idasal, Mexan, Pressomin, Vasosterol, Vasoxine, Vasoxyl, and Vasylox.[3][4][6]
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.[4][6] However, it was discontinued in Canada and the United Kingdom by 2004.[7] It has also been discontinued in the United States.[1] By 2016, methoxamine appeared to remain available only in Japan.[6]