Dichloroisoprenaline

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Dichloroisoprenaline
Dichloroisoprenaline.svg
Names
Preferred IUPAC name
Dichloroisoprenaline
Systematic IUPAC name
1-(3,4-Dichlorophenyl)-2-[(propan-2-yl)amino]ethan-1-ol
Other names
1-(3,4-Dichlorophenyl)-2-(isopropylamino)ethanol
Dichlorisoproterenol
Identifiers
59-61-0 N
ChEBI CHEBI:144234 N
ChEMBL ChEMBL30816 YesY
ChemSpider 5601 (1R) YesY
5324297 (1S) YesY
5601 () YesY
Jmol 3D model Interactive image
Interactive image
KEGG C11772 N
MeSH Dichloroisoproterenol
PubChem 5806 (1R)
6951395 (1S)
5806 ()
Properties
C11H15Cl2NO
Molar mass 248.15 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YesYN ?)
Infobox references

Dichloroisoprenaline (DCI), also known as dichloroisoproterenol, was the first beta blocker ever to be developed. It is non-selective for the β1-adrenergic and β2-adrenergic receptors. DCI has low potency and acts as a partial agonist/antagonist at these receptors.[1]

Although DCI was of no clinical value itself, further developments from DCI eventually led to the development of the clinical candidate pronethalol (withdrawn due to carcinogenicity) and subsequently propranolol (the first clinically successful beta blocker).

Dichloroisoprenaline is a racemic mixture of enantiomers.

The two enantiomers of dichloroisoprenaline

References[edit]

  1. ^ W. E. Glover; A. D. M. Greenfield; R. G. Shanks (October 1962). "Effect of dichloroisoprenaline on the peripheral vascular responses to adrenaline in man". Br J Pharmacol Chemother 19: 235–244. doi:10.1111/j.1476-5381.1962.tb01185.x. PMC 1482134. PMID 13948521.