Bucindolol is a non-selective

beta blocker Beta blockers, also spelled β-blockers, are a class of medications that are predominantly used to manage abnormal heart rhythms ( arrhythmia), and to protect the heart from a second heart attack after a first heart attack ( secondary prevention ...

with additional weak alpha-blocking properties and

intrinsic sympathomimetic activity Beta blockers, also spelled β-blockers, are a class of medications that are predominantly used to manage abnormal heart rhythms (arrhythmia), and to protect the heart from a second heart attack after a first heart attack (secondary prevention). ...

in some model systems but not in human hearts. It was under review by the

FDA The United States Food and Drug Administration (FDA or US FDA) is a federal agency of the Department of Health and Human Services. The FDA is responsible for protecting and promoting public health through the control and supervision of food ...

in the

United States The United States of America (USA), also known as the United States (U.S.) or America, is a country primarily located in North America. It is a federal republic of 50 U.S. state, states and a federal capital district, Washington, D.C. The 48 ...

for the treatment of

heart failure Heart failure (HF), also known as congestive heart failure (CHF), is a syndrome caused by an impairment in the heart's ability to Cardiac cycle, fill with and pump blood. Although symptoms vary based on which side of the heart is affected, HF ...

in 2009, but was rejected due to issues pertaining to integrity of data submitted.

Synthesis

The displacement of the dimethylamino group in

gramine Gramine (also called donaxine) is a naturally occurring indole alkaloid present in several plant species. Gramine may play a defensive role in these plants, since it is toxic to many organisms. Occurrence Gramine has been found in the giant reed, ...

(1) by the anion from

2-nitropropane 2-Nitropropane (2-NP) is an organic compound with the formula . It is used as a solvent. It is a colorless liquid and is classified as a nitro compound. Preparation 2-Nitropropane is produced by the high-temperature vapor-phase nitration of pro ...

gives 3-(2-methyl-2-nitropropyl)indole (2), which is

reduced Reduction, reduced, or reduce may refer to: Science and technology Chemistry * Reduction (chemistry), part of a reduction-oxidation (redox) reaction in which atoms have their oxidation state changed. ** Organic redox reaction, a redox reacti ...

to the

amine In chemistry, amines (, ) are organic compounds that contain carbon-nitrogen bonds. Amines are formed when one or more hydrogen atoms in ammonia are replaced by alkyl or aryl groups. The nitrogen atom in an amine possesses a lone pair of elec ...

alpha,alpha-dimethyltryptamine (3). Separately, the reaction of 2-hydroxybenzonitrile (4) with

epichlorohydrin Epichlorohydrin (abbreviated ECH) is an organochlorine compound and an epoxide. Despite its name, it is not a halohydrin. It is a colorless liquid with a pungent, garlic-like odor, moderately soluble in water, but miscibility, miscible with most p ...

gives the

epoxide In organic chemistry, an epoxide is a cyclic ether, where the ether forms a three-atom ring: two atoms of carbon and one atom of oxygen. This triangular structure has substantial ring strain, making epoxides highly reactive, more so than other ...

(5). Combination of the two intermediates (3) and (5) gives bucindolol.

References

Antihypertensive agents Beta blockers 2-Hydroxybenzonitrile ethers N-Monoalkyltryptamines N-tert-butyl-phenoxypropanolamines {{antihypertensive-stub

Synthesis

See also

References