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Dopexamine

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Dopexamine
Dopexamine.png
Systematic (IUPAC) name
4-[2-({6-[(2-phenylethyl)amino]hexyl}amino)ethyl]benzene-1,2-diol
Clinical data
AHFS/Drugs.com International Drug Names
Identifiers
CAS Number 86197-47-9 YesY
ATC code C01CA14
PubChem CID 55483
ChemSpider 50102 YesY
UNII 398E7Z7JB5 YesY
KEGG D03891 YesY
ChEMBL CHEMBL77622 YesY
Chemical data
Formula C22H32N2O2
Molar mass 429.43 g/mol
  (verify)

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]

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[edit]

  1. ^ Perrin G, Papazian L, Martin C. (1993). "Dopexamine: a new dopaminergic agonist". Ann Fr Anesth Reanim. 12 (3): 308–320. PMID 7902685. 
  2. ^ 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. 
  3. ^ 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. 
  4. ^ 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. 
  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).


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