Bucindolol
Chemical compound
From Wikipedia, the free encyclopedia
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]
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| ECHA InfoCard | 100.114.291 |
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| Formula | C22H25N3O2 |
| Molar mass | 363.461 g·mol−1 |
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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]