ethaverine

Chemical Properties

Crystals.Insoluble in water; very soluble in hot alcohol; slightly soluble in ether and chloroform.

Originator

Ethaverine,Shanghai Lansheng

Uses

Ethaverine is an analogue of Papaverine (P190500), an antispasmodic. An isoquinoline derivative with the potential for antimicrobial, antimalarial and cytotoxic antiviral agents.

Definition

ChEBI: 1-[(3,4-diethoxyphenyl)methyl]-6,7-diethoxyisoquinoline is a member of isoquinolines.

Manufacturing Process

(1) 1 part of 2-(3,4-diethoxy-phenyl)-N-[2-(3,4-diethoxy-phenyl)-2-hydroxyethyl]acetamide (homoveratroyl hydroxyhomo-veratrylamine), prepared from 2-amino-1-(3,4-diethoxy-phenyl)ethanol and (3,4-diethoxy-phenyl)acetyl chloride, is dissolved in a neutral solvent, such as, for example, chloroform or benzene. Thereupon, 1 to 3 parts of phosphorus oxychloride are added to the resulting solution and the no whole is heated for some hours under a reflux condenser. It should be pointed out here that it is also possible to occur by allowing the amide solution to flow on to the phosphorus oxychloride with the application of heat or in the cold. Instead of this, it is also possible to carry out the reaction in such a way that the reaction mixture is first allowed to stand in the cold. Then it completed by heating. The base produced in both cases is obtained by shaking with chloroform after distilling off the solvent and after alkalization. MP: 145°-147°C.
(2) 1 part of 2-(3,4-dimethoxyphenyl)ethylamine is dissolved in 2 parts of benzene, 1 to 2 parts of phosphorus pentachloride are added thereto and the whole is heated to boiling. After heating for several hours, the base, which is formed can be isolated as above described. MP: 147°C.
(3) 1 part of N-(3,4-diethoxyphenylacetyl)-β-oxy-β-(3,4- diethoxyphenyl)ethylamine is dissolved in benzene or chloroform, mixed with 1 to 3 parts by weight of phosphorus oxychloride and boiled under a reflux condenser for 3 hours whereupon 6,7-diethoxy-1-(3',4'- diethoxybenzyl)isoquinoline base can be isolated in the usual way. MP: 99°- 101°C.

Therapeutic Function

Spasmolytic, Vasodilator, Antiarrhythmic