4356. Gallopamil

Nomenclature

CAS number: 16662-47-8
α-[3-[[2-(3,4-Dimethoxyphenyl)ethyl]methylamino]propyl]-3,4,5-trimethoxy-α-(1-methylethyl)benzeneacetonitrile; 5-[(3,4-dimethoxyphenethyl)methylamino]-2-isopropyl-2-(3,4,5-trimethoxyphenyl)valeronitrile; α-isopropyl-α-[(N-methyl-N-homoveratryl)-γ-aminopropyl]-3,4,5-trimethoxyphenylacetonitrile; methoxyverapamil; D-600.
C28H40N2O5; mol wt 484.63.
C 69.39%, H 8.32%, N 5.78%, O 16.51%.

Description and references

Calcium channel blocking agent; methoxy analog of verapamil, q.v. Prepn: F. Dengel, BE 615861; idem, US 3261859 (1962, 1966 to Knoll). Stereoselective synthesis of enantiomers: L. J. Theodore, W. L. Nelson, J. Org. Chem. 52, 1309 (1987). Pharmacology: H. Haas, E. Busch, Arzneim.-Forsch. 17, 257 (1967); eidem, ibid. 18, 401 (1968); A. Fleckenstein, ibid. 20, 1317 (1970). Clinical trial in stable angina pectoris: N. S. Khurmi et al., Am. J. Cardiol. 53, 684 (1984). Symposium on pharmacology and clinical efficacy: J. Cardiovasc. Pharmacol. 20, Suppl. 7, S1-S95 (1992). Review of pharmacokinetics and therapeutic potential in ischemic heart disease: R. N. Brogden, P. Benfield, Drugs 47, 93-115 (1994).

Chemical structure

Properties

Pale yellow viscous oil. nD25 1.5402.

Derivative

Hydrochloride.

Nomenclature

CAS number: 16662-46-7
Algocor (Ravizza); Procorum (Knoll).
C28H40N2O5.HCl; mol wt 521.09.
C 64.54%, H 7.93%, N 5.38%, O 15.35%, Cl 6.80%.

Properties

mp 145-148°.

Derivative

d-Form hydrochloride.

Nomenclature

CAS number: 38176-09-9

Properties

White crystalline solid from propanol/cyclohexane, mp 160.5-161.5°. [α]D25 +11.7° (c = 5.02 in ethanol).

Derivative

l-Form hydrochloride.

Nomenclature

CAS number: 36222-39-6

Properties

White crystalline solid from propanol/cyclohexane, mp 160.5-161.5°. [α]D23 11.7° (c = 5.04 in ethanol).

Therapeutic Category

Antianginal.

Keywords

Antianginal; Calcium Channel Blocker; Arylalkylamines