2894. Denopamine

Nomenclature

CAS number: 71771-90-9
(αR)-α-[[[2-(3,4-Dimethoxyphenyl)ethyl]amino]methyl]-4-hydroxybenzenemethanol; (-)-(R)-α-[[(3,4-dimethoxyphenethyl)amino]methyl]-p-hydroxybenzyl alcohol; (-)-(R)-1-(4-hydroxyphenyl)-2-(3,4-dimethoxyphenethylamino)ethanol; TA-064; Carguto (Tanabe Seiyaku); Kalgut (Tanabe Seiyaku).
C18H23NO4; mol wt 317.38.
C 68.12%, H 7.30%, N 4.41%, O 20.16%.

Description and references

Selective β1-adrenoceptor agonist with positive inotropic activity. Prepn: M. Ikezaki et al., BE 833731; eidem, US 4032575 (1976, 1977 both to Tanabe Seiyaku); N. Umino et al., Chem. Pharm. Bull. 27, 1479 (1979). Effect on carbohydrate and lipid metabolism in rats: M. Inamasu et al., Biochem. Pharmacol. 33, 2171 (1984). Cardiovascular pharmacology in animals: T. Nagao et al., Jpn. J. Pharmacol. 35, 415 (1984); in humans: M. Kino et al., Am. J. Cardiol. 51, 802 (1983). Metabolism in humans: T. Suzuki et al., Drug Metab. Dispos. 11, 377 (1983). GC-MS determn in human urine: eidem, Chem. Pharm. Bull. 33, 2549 (1985). Binding affinity and selectivity: K. Naito et al., Jpn. J. Pharmacol. 38, 235 (1985). Clinical efficacy in congestive cardiomyopathy: J. Thormann et al., Am. Heart J. 110, 426 (1985). Series of articles on pharmacokinetics, metabolism and disposition in animals: Arzneim.-Forsch. 36, 643-667 (1986).

Chemical structure

Derivative

l-Form hydrochloride.
C18H23NO4.HCl; mol wt 353.84.
C 61.10%, H 6.84%, N 3.96%, O 18.09%, Cl 10.02%.

Properties

Crystals from isopropanol, mp 138-139.5°. [α]D25 -38.0° (c = 1 in methanol).

Derivative

dl-Form hydrochloride.

Properties

Crystals from isopropanol + isopropyl ether, mp 164-167°.

Therapeutic Category

Cardiotonic.

Keywords

β-Adrenergic Agonist; Cardiotonic