Grundinformationen
- Standard-SMILES
COc1ccc(OC)c(C(O)C(C)N)c1- InChIKey
WJAJPNHVVFWKKL-UHFFFAOYSA-N- Summenformel
- C11H17NO3
- Durchschnittliche Molmasse
- 211,26 g/mol
- Monoisotopische Masse
- 211,1208434
Überblick
Methoxamine is an amphetamine in which the parent 1-phenylpropan-2-amine skeleton is substituted at position 1 with an hydroxy group and the phenyl ring is 2- and 5-substituted with methoxy groups. It is an antihypotensive agent (pressor), an agonist acting directly at alpha-adrenoceptors with selectivity for the alpha-1 adrenoceptor subtype similar to phenylephrine. It has a role as an antihypotensive agent and an alpha-adrenergic agonist.
Namen und Bezeichner
- Bevorzugter Name
- Methoxamine
- IUPAC
- 2-amino-1-(2,5-dimethoxyphenyl)propan-1-ol
Namen und Synonyme
methoxamineMethoxamin390-28-32-amino-1-(2,5-dimethoxyphenyl)propan-1-olMethoxamedrinePseudomethoxamineMetossaminaCHEBI:6839Benzenemethanol, alpha-(1-aminoethyl)-2,5-dimethoxy-NRL001DTXSID0023290NRL-001
Weitere Namen anzeigen
MethoxamedrinVasoxinWellcome, MetoxamineRefChem:811759DTXCID403290206-867-3HUQ1KC1YLI2,5-Dimethoxynorephedrine
Datenbank-Bezeichner
- CAS
390-28-3- PubChem CID
- 6082
- DTXSID
DTXSID0023290- ChEMBL
CHEMBL524- ChEBI
CHEBI:6839- EC Number
- 206-867-3
- Nikkaji
- J5.717G
Eigenschaften
Berechnete Struktureigenschaften
- XLogP
- 0,5
- Polarare Oberfläche (TPSA)
- 64,7 Ų
- H-Brücken-Donoren
- 2
- H-Brücken-Akzeptoren
- 4
- Frei drehbare Bindungen
- 4
- Schwere Atome
- 15
- Formalladung
- 0
- Komplexität
- 189
Experimentelle und physikochemische Eigenschaften
LogP0.8
Solubility
Soluble (185 g/L)
9.21e+00 g/L
Human DrugsPharmaceuticals
Physical DescriptionSolid
Collision Cross Section148.43 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
Sicherheit und Regulatorisches
Toxikologische Informationen
Drug Induced Liver Injury
Drug-Induced Liver Injury Severity and Toxicity (DILIst)
methoxamine
DILI Negative
Intramuscular; Intravenous
DOI:10.1016/j.drudis.2019.09.022
Chemie und Industrie
Pharmakologische Informationen
ATC Code
C - Cardiovascular system
QC - Cardiovascular system
Protein BindingLow
Pharmacodynamics
Methoxamine is a potent sympathomimetic amine that increases both systolic and diastolic blood pressure. Methoxamine is indicated for prevention and treatment of the acute hypotensive state occurring with spinal anesthesia. It is also indicated as adjunctive treatment of hypotension due to hemorrhage, reactions to medications, surgical complications, and shock associated with brain damage due to trauma or tumor. Methoxamine acts on both α1-adrenergic receptors but appears to have no effect on β-adrenergic receptors. It acts by increasing the force of the heart's pumping action as well as constricting peripheral blood vessels.
Mechanism of ActionMethoxamine acts through peripheral vasoconstriction by acting as a pure alpha-1 adrenergic receptor agonist, consequently increasing systemic blood pressure (both systolic and diastolic).
MeSH Pharmacological Classification
Drugs that mimic the effects of stimulating postganglionic adrenergic sympathetic nerves. Included here are drugs that directly stimulate adrenergic receptors and drugs that act indirectly by provoking the release of adrenergic transmitters.
Drugs used to cause constriction of the blood vessels.
Compounds that bind to and activate ADRENERGIC ALPHA-1 RECEPTORS.
Cellular LocationsMembrane
Verwendung und Herstellung
Use ClassificationPharmaceuticals
Zugehörige Reaktionen
7
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