fenetylline hydrochloride

Description

Fenethylline is a combination of the drugs amphetamine and theophylline. It was formerly used to treat conditions such as ADHD, narcolepsy, and depression; but its use has been banned because of the potential for abuse.
Chemists at the German drug company Degussa AG first synthesized fenethylline in 1961 from amphetamine and 7-(2-chloroethyl)theophylline. The company soon began to market its hydrochloride salt (shown) under the trade name Captagon. Its sales continued until 1986, when most countries outlawed it.
Fenethylline re-emerged this year because of its widespread abuse by Middle Eastern young adults. It is promoted by terrorist groups such as the Islamic State to enhance what they consider to be desirable characteristics—aggressiveness, alertness, and fearlessness—in their recruits.
In the body, enzymes oxidize fenethylline to produce its original components, amphetamine and theophylline, each of which has its own undesirable characteristics when taken in large quantities. To counteract these effects, Cody J. Wenthur, Bin Zhou, and Kim D. Janda* at the Scripps Research Institute (La Jolla, CA) developed?protein-conjugate vaccines that disarm fenethylline and its constituents’ abilities to affect brain activity. ?
The authors’ next objective is to develop a combination vaccine for treating fenethylline addiction.

Originator

Captagon,Homburg,W. Germany,1961

The Uses of fenetylline hydrochloride

CNS stimulant. Controlled substance.

Manufacturing Process

1 mol of 7-(β-chloroethyl)-theophylline and 2? mols of α-methyl-β-phenyl ethylamine are heated for 6 hours in an oil bath, if necessary with addition of alcohol or toluene. The reaction mixture is diluted with alcohol and acidified with alcoholic hydrochloric acid. The crystalline mass formed is filtered with suction and extracted by boiling with alcohol. A product having a melting point of 237°C to 239°C is formed. With prolonged extraction by boiling with alcohol, the melting point of the mass falls, preferably due to a change in modification, to 227°C to 229°C. However, analysis shows that both products are the pure condensation product.
Instead of the chloroethyl theophylline, it is also possible to use the corresponding bromine derivative. It was found that in this way the process is facilitated and the yield is improved

Therapeutic Function

Central stimulant