Dopexamine

Dopexamine

Dopexamine
Systematic (IUPAC) name
4-[2-({6-[(2-phenylethyl)amino]hexyl}amino)ethyl]benzene-1,2-diol
Clinical data
AHFS/Drugs.com
Identifiers
CAS Registry Number  YesY
ATC code C01
PubChem CID:
ChemSpider  YesY
UNII  YesY
KEGG  YesY
ChEMBL  YesY
Chemical data
Formula C22H32N2O2
Molecular mass 429.43 g/mol
 YesY   

Dopexamine is a synthetic analogue of dopamine. Despite this, it is a β1 and β2-adrenergic receptor agonist.[1] Its action at dopamine receptor D1 mediates relaxation of vascular smooth muscle in renal, mesenteric, cerebral and coronary arteries. Mild action at D2 receptors decreases noradrenaline release.[2]

Use in sepsis has been proposed.[3]

It is used as an inotropic agent in cardiac failure.[4] Side effects include arrhythmia, tremor, angina and flushing.

Synthesis

Dopexamine synthesis:[5]

Condensation of the adipic acid derivative 1 with phenethylamine in the presence of Carbonyldiimidazole affords bis-adipic acid amide 2. The synthesis is completed by reduction of the carbonyl groups with diborane followed by demethylation of the aromatic methoxy groups with hydrogen bromide to afford dopexamine.

References

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  5. ^ J. B. Farmer, F. Ince, R. A. Brown, and J. Dixon, U.S. Patent 5,013,760 via Chem. Abstr., 99: 53,408q (1983). Anon. Drugs of the Future, 10, 628 (1985).