Dopexamine
| Systematic (IUPAC) name | |
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4-[2-({6-[(2-phenylethyl)amino]hexyl}amino)ethyl]benzene-1,2-diol
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| Clinical data | |
| AHFS/Drugs.com | International Drug Names |
| Identifiers | |
| CAS Number | 86197-47-9 |
| ATC code | C01CA14 |
| PubChem | CID 55483 |
| ChemSpider | 50102 |
| UNII | 398E7Z7JB5 |
| KEGG | D03891 |
| ChEMBL | CHEMBL77622 |
| Chemical data | |
| Formula | C22H32N2O2 |
| Molar mass | 429.43 g/mol |
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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[edit]
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[edit]
- ^ Perrin G, Papazian L, Martin C. (1993). "Dopexamine: a new dopaminergic agonist". Ann Fr Anesth Reanim. 12 (3): 308–320. PMID 7902685.
- ^ Brown RA, Dixon J, Farmer JB; et al. (July 1985). "Dopexamine: a novel agonist at peripheral dopamine receptors and beta 2-adrenoceptors". Br. J. Pharmacol. 85 (3): 599–608. doi:10.1111/j.1476-5381.1985.tb10554.x. PMC 1916510. PMID 2862944.
- ^ Birnbaum J, Klotz E, Spies CD; et al. (2006). "Effects of dopexamine on the intestinal microvascular blood flow and leucocyte activation in a sepsis model in rats". Crit Care 10 (4): R117. doi:10.1186/cc5011. PMC 1750974. PMID 16893450.
- ^ Lisbon A (May 2003). "Dopexamine, dobutamine, and dopamine increase splanchnic blood flow: what is the evidence?". Chest 123 (5 Suppl): 460S–3S. doi:10.1378/chest.123.5_suppl.460S. PMID 12740229.
- ^ 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).
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