From Wikipedia, the free encyclopedia
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
Identifiers
ChEBI
ChEMBL
ChemSpider
KEGG
MeSH
Dichloroisoproterenol
UNII
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
CC(C)NCC(O)C1=CC(Cl)=C(Cl)C=C1
Clc1ccc(cc1Cl)C(O)CNC(C)C
Properties
C11 H15 Cl2 NO
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).
Chemical compound
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value itself, further developments from DCI eventually led to the development of the clinical candidate pronethalol (withdrawn due to carcinogenicity ) and subsequently propranolol (the first clinically successful beta blocker).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
α1
Agonists Antagonists
Abanoquil Ajmalicine Alfuzosin Anisodamine Anisodine Atiprosin Atypical antipsychotics (e.g., brexpiprazole , clozapine , olanzapine , quetiapine , risperidone )Benoxathian Beta blockers (e.g., adimolol , amosulalol , arotinolol , carvedilol , eugenodilol , labetalol )Buflomedil Bunazosin Corynanthine Dapiprazole Domesticine Doxazosin Ergolines (e.g., acetergamine , ergotamine , dihydroergotamine , lisuride , nicergoline , terguride )Etoperidone Fenspiride Hydroxyzine Indoramin Ketanserin L-765,314 mCPP Mepiprazole Metazosin Monatepil Moxisylyte Naftopidil Nantenine Neldazosin Niaprazine Niguldipine Pardoprunox Pelanserin Perlapine Phendioxan Phenoxybenzamine Phentolamine Phenylpiperazine antidepressants (e.g., hydroxynefazodone , nefazodone , trazodone , triazoledione )Piperoxan Prazosin Quinazosin Quinidine Silodosin Spegatrine Spiperone Talipexole Tamsulosin Terazosin Tiodazosin Tolazoline Tetracyclic antidepressants (e.g., amoxapine , maprotiline , mianserin )Tricyclic antidepressants (e.g., amitriptyline , clomipramine , doxepin , imipramine , trimipramine )Trimazosin Typical antipsychotics (e.g., chlorpromazine , fluphenazine , loxapine , thioridazine )Urapidil WB-4101 Zolertine
α2
Agonists Antagonists
1-PP Adimolol Amesergide Aptazapine Atipamezole Atypical antipsychotics (e.g., asenapine , brexpiprazole , clozapine , lurasidone , olanzapine , paliperidone , quetiapine , risperidone , zotepine )Azapirones (e.g., buspirone , gepirone , ipsapirone , tandospirone )BRL-44408 Buflomedil Cirazoline Efaroxan Esmirtazapine Fenmetozole Fluparoxan Idazoxan Ketanserin Lisuride mCPP Mianserin Mirtazapine NAN-190 Pardoprunox Phentolamine Phenoxybenzamine Piperoxan Piribedil Rauwolscine Rotigotine Setiptiline Spegatrine Spiroxatrine Sunepitron Terguride Tolazoline Typical antipsychotics (e.g., chlorpromazine , fluphenazine , loxapine , thioridazine )Yohimbine
β
