Denopamine (

INN Inns are generally establishments or buildings where travelers can seek lodging, and usually, food and drink. Inns are typically located in the country or along a highway; before the advent of motorized transportation they also provided accommo ...

) is a cardiotonic drug which acts as a β₁ adrenergic receptor

agonist An agonist is a chemical that activates a receptor to produce a biological response. Receptors are cellular proteins whose activation causes the cell to modify what it is currently doing. In contrast, an antagonist blocks the action of the ago ...

. It is used in the treatment of

angina Angina, also known as angina pectoris, is chest pain or pressure, usually caused by ischemia, insufficient blood flow to the Cardiac muscle, heart muscle (myocardium). It is most commonly a symptom of coronary artery disease. Angina is typical ...

and may also have potential uses in the treatment of

congestive heart failure Heart failure (HF), also known as congestive heart failure (CHF), is a syndrome, a group of signs and symptoms caused by an impairment of the heart's blood pumping function. Symptoms typically include shortness of breath, excessive fatigue, a ...

and for clearing

pulmonary oedema Pulmonary edema, also known as pulmonary congestion, is excessive liquid accumulation in the tissue and air spaces (usually alveoli) of the lungs. It leads to impaired gas exchange and may cause hypoxemia and respiratory failure. It is due to ...

. It is marketed in Japan under the brand name Kalgut (カルグート) and available as tablets of 5 and 10 mg, and 5% fine granules.

Synthesis

According to the patent, Denopamine can be used as either an antidiabetic or a cardiotonic. Denopamine synthesis

The reaction between 1-(4-benzyloxyphenyl)-2-chloroethanone 3365-56-0(1) and 3,4-Dimethoxyphenethylamine 20-20-7(

DMPEA DMPEA can refer to two subclasses of substituted phenethylamines: Dimethoxy-phenethylamines * 2,3-Dimethoxyphenethylamine * 2,4-Dimethoxyphenethylamine * 2,5-Dimethoxyphenethylamine * 2,6-Dimethoxyphenethylamine * 3,4-Dimethoxyphenethylamine ...

) (2) give
CID:10993165
(3). The reduction of the ketone with sodium borohydride gav
CID:12940814
(4). Catalytic hydrogenation cleaves the benzyl group giving (5).

References

Beta1-adrenergic agonists Phenylethanolamines Catechol ethers Phenols {{cardiovascular-drug-stub