Bucindolol

Bucindolol is a non-selective beta blocker with additional weak alpha-blocking properties and intrinsic sympathomimetic activity in some model systems^[1][2] but not in human hearts.^[3][4] It was under review by the FDA in the United States for the treatment of heart failure in 2009, but was rejected due to issues pertaining to integrity of data submitted.^[5]

Bucindolol

Clinical data
ATC code	none
Identifiers
IUPAC name 2-[2-hydroxy-3-[[2-(1H-indol-3-yl)-1,1-dimethyl-ethyl]amino]propoxy]benzonitrile
CAS Number	71119-11-4
PubChem CID	51045
ChemSpider	46266
UNII	E9UO06K7CE
ChEMBL	ChEMBL2107546
CompTox Dashboard (EPA)	DTXSID3046744
ECHA InfoCard	100.114.291
Chemical and physical data
Formula	C22H25N3O2
Molar mass	363.461 g·mol−1
3D model (JSmol)	Interactive image
SMILES N#Cc0ccccc0OCC(O)CNC(C)(C)Cc1c[nH]c2c1cccc2

Synthesis

The displacement of the dimethylamino group in gramine (1) by the anion from 2-nitropropane gives 3-(2-methyl-2-nitropropyl)indole (2), which is reduced to the amine alpha,alpha-dimethyltryptamine (3). Separately, the reaction of 2-hydroxybenzonitrile (4) with epichlorohydrin gives the epoxide (5). Combination of the two intermediates (3) and (5) gives bucindolol.^[6][7]

See also

• Epanolol
• Primidolol