Methoxamine

Not to be confused with methoxetamine.

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]

Methoxamine

Clinical data
Trade names	Vasoxine, Vasoxyl, Vasylox, others
Other names	Methoxamedrine; 2,6-Dimethoxy-β-hydroxy-α-methylphenethylamine; 2,6-Dimethoxy-β-hydroxyamphetamine
AHFS/Drugs.com	International Drug Names
Routes of administration	Oral, injection[1]
ATC code	C01CA10 (WHO)
Pharmacokinetic data
Elimination half-life	3 hours
Excretion	Urine
Identifiers
IUPAC name 2-amino-1-(2,5-dimethoxyphenyl)propan-1-ol
CAS Number	390-28-3 Y
PubChem CID	6082
IUPHAR/BPS	483
DrugBank	DB00723 Y
ChemSpider	5857 Y
UNII	HUQ1KC1YLI
KEGG	D08201 Y
ChEMBL	ChEMBL524 Y
CompTox Dashboard (EPA)	DTXSID0023290
ECHA InfoCard	100.006.244
Chemical and physical data
Formula	C11H17NO3
Molar mass	211.261 g·mol−1
3D model (JSmol)	Interactive image
SMILES O(c1ccc(OC)cc1C(O)C(N)C)C
InChI InChI=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 Y Key:WJAJPNHVVFWKKL-UHFFFAOYSA-N Y
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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 2,6-dimethoxy-β-hydroxy-α-methylphenethylamine or as 2,6-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 INNTooltip International Nonproprietary Name and BANTooltip British Approved Name, while méthoxamine is its DCFTooltip Dénomination Commune Française and methoxamina is its DCITTooltip Denominazione Comune Italiana.^[3][4][6] In the case of the hydrochloride salt, its generic name is methoxamine hydrochloride and this is its USANTooltip United States Adopted Name, BANMTooltip British Approved Name, and JANTooltip Japanese Accepted Name.^[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]