Bunitrolol

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| ImageFile = Bunitrolol.svg

| ImageSize = 200px

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| IUPACName = 2-[3-(tert-Butylamino)-2-hydroxypropoxy]benzonitrile

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|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

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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

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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