View source for Dichloroisoprenaline

{{Chembox
|  ImageFile = Dichloroisoprenaline.svg 
|   ImageSize = 200px
|  PIN = Dichloroisoprenaline
|  SystematicName = 1-(3,4-Dichlorophenyl)-2-[(propan-2-yl)amino]ethan-1-ol
|  OtherNames = 1-(3,4-Dichlorophenyl)-2-(isopropylamino)ethanol<br />
Dichlorisoproterenol
| Section1 = {{Chembox Identifiers
|  CASNo = 59-61-0
|  PubChem = 443400
|   PubChem_Comment = (1''R'')
|   PubChem_Ref = {{pubchemcite}}
|   PubChem1 = 6951395
|   PubChem1_Comment = (1''S'')
|   PubChem1_Ref = {{pubchemcite}}
|   PubChem2 = 5806
|   PubChem2_Comment = ()
|   PubChem2_Ref = {{pubchemcite}}
|  ChemSpiderID = 391627
|   ChemSpiderID_Comment = (1''R'')
|   ChemSpiderID_Ref = {{chemspidercite}}
|   ChemSpiderID1 = 5324297
|   ChemSpiderID1_Comment = (1''S'')
|   ChemSpiderID1_Ref = {{chemspidercite}}
|   ChemSpiderID2 = 5601
|   ChemSpiderID2_Comment = ()
|   ChemSpiderID2_Ref = {{chemspidercite}}
|  KEGG = C11772
|  MeSHName = Dichloroisoproterenol
|  ChEBI = 144234
|  SMILES = CC(C)NCC(O)C1=CC(Cl)=C(Cl)C=C1
|  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
|  InChIKey = VKMGSWIFEHZQRS-UHFFFAOYSA-N}}
|Section2={{Chembox Properties
|  Formula=C<sub>11</sub>H<sub>15</sub>Cl<sub>2</sub>NO
|  MolarMass=248.15 g/mol
|  Appearance=
|  Density=
|  MeltingPt=
|  BoilingPt=
|  Solubility=
  }}
|Section3={{Chembox Hazards
|  MainHazards=
|  FlashPt=
|  Autoignition=
  }}
}}

'''Dichloroisoprenaline''' ('''DCI'''), also known as '''dichlorosisoproterenol''', was the first [[beta blocker]] ever to be developed. It is non-selective for the [[β1-adrenergic|β<sub>1</sub>-adrenergic]] and [[β2-adrenergic|β<sub>2</sub>-adrenergic receptor]]s. DCI has low [[potency]] and acts as a [[partial agonist]]/[[receptor_antagonist|antagonist]] at these [[receptor]]s.

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itself, further developments from DCI eventually led to the development of the clinical candidate [[pronethalol]] (withdrawn due to [[carcinogenicity]]) and subsequently [[propranolol]] (the first clinically-successful beta blocker).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.

[[File:(±)-Dichlorosisoproterenol Enantiomers Structural Formulae.png|thumb|left|The two enantiomers of dichloroisoprenaline]]{{clear-left}}

== References ==
{{reflist}}

{{chem-stub}}

{{Adrenergics}}

[[Category:Beta blockers]]
[[Category:Organochlorides]]
[[Category:Phenethylamines]]
[[Category:Alcohols]]
[[Category:2Fix]]