Dichloroisoprenaline

Dichloroisoprenaline

Names
Preferred 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
CAS Number	59-61-0^Y
3D model (JSmol)	Interactive image Interactive image
ChEBI	CHEBI:144234^N
ChEMBL	ChEMBL30816^Y
ChemSpider	5601 (1R)^Y 5324297 (1S)^Y 5601 ()^Y
KEGG	C11772^N
MeSH	Dichloroisoproterenol
PubChem CID	5806 (1R) 6951395 (1S) 5806 ()
UNII	U7NOE2K4M2^Y
CompTox Dashboard (EPA)	DTXSID20874225
InChI InChI=1S/C11H15Cl2NO/c1-7(2)14-6-11(15)8-3-4-9(12)10(13)5-8/h3-5,7,11,14-15H,6H2,1-2H3^Y Key: VKMGSWIFEHZQRS-UHFFFAOYSA-N^Y InChI=1/C11H15Cl2NO/c1-7(2)14-6-11(15)8-3-4-9(12)10(13)5-8/h3-5,7,11,14-15H,6H2,1-2H3 Key: VKMGSWIFEHZQRS-UHFFFAOYAS
SMILES CC(C)NCC(O)C1=CC(Cl)=C(Cl)C=C1 Clc1ccc(cc1Cl)C(O)CNC(C)C
Properties
Chemical formula	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 ^YN ?) 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value itself, further developments from DCI eventually led to the development of the clinical candidate pronethalol (withdrawn due to carcinogenicity) and subsequently propranolol (the first clinically successful beta blocker).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

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 (2): 235–244. doi:10.1111/j.1476-5381.1962.tb01185.x. PMC 1482134. PMID 13948521.