Bunitrolol
{{Chembox
| ImageFile = Bunitrolol.svg
| ImageSize = 200px
| ImageAlt =
| ImageFile2 =
| IUPACName = 2-[3-(tert-Butylamino)-2-hydroxypropoxy]benzonitrile
| OtherNames =
|Section1={{Chembox Identifiers
| CASNo = 34915-68-9
| PubChem = 2473
| ChemSpiderID = 2379
| ChEMBL = 418134
| KEGG = D01444
| UNII = F2613LO055
| InChI = 1/C14H20N2O2/c1-14(2,3)16-9-12(17)10-18-13-7-5-4-6-11(13)8-15/h4-7,12,16-17H,9-10H2,1-3H3
| InChIKey = VCVQSRCYSKKPBA-UHFFFAOYAU
| StdInChI = 1S/C14H20N2O2/c1-14(2,3)16-9-12(17)10-18-13-7-5-4-6-11(13)8-15/h4-7,12,16-17H,9-10H2,1-3H3
| StdInChIKey = VCVQSRCYSKKPBA-UHFFFAOYSA-N
| SMILES = CC(C)(C)NCC(COC1=CC=CC=C1C#N)O}}
|Section2={{Chembox Properties
| C=14 | H=20 | N=2 | O=2
| Appearance =
| Density =
| MeltingPt =
| BoilingPt =
| Solubility = }}
|Section3={{Chembox Hazards
| MainHazards =
| FlashPt =
| AutoignitionPt = }}
}}
Bunitrolol is a beta-adrenergic antagonist.{{cite journal|pmid=20310018|year=2010|last1=Haddad|first1=S|last2=Poulin|first2=P|last3=Funk|first3=C|title=Extrapolating in vitro metabolic interactions to isolated perfused liver: Predictions of metabolic interactions between R-bufuralol, bunitrolol, and debrisoquine|volume=99|issue=10|pages=4406–26|doi=10.1002/jps.22136|journal=Journal of Pharmaceutical Sciences}}
Synthesis
2-Hydroxybenzonitrile (1) is treated with epichlorohydrin and sodium hydroxide to give the epoxide (2). Addition of tert-butylamine completes the synthesis of bunitrolol.Herbert Koppe, Albrecht Engelhardt, Karl Zeile, {{US patent|3940489}} (1976 to Boehringer Ingelheim Gmbh).
See also
References
{{Reflist}}
{{Adrenergics}}
Category:2-Hydroxybenzonitrile ethers
Category:N-tert-butyl-phenoxypropanolamines
{{cardiovascular-drug-stub}}