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Fenethylline

Fenethylline
Systematic (IUPAC) name
(RS)-1,3-dimethyl- 7-[2-(1-phenylpropan-2-ylamino)ethyl]purine- 2,6-dione
Identifiers
CAS number 3736-08-1
ATC code N06BA10
PubChem CID 19527
DrugBank N/A
ChemSpider 18398 YesY
Chemical data
Formula C18H23N5O2 
Mol. mass 341.408 g/mol
SMILES eMolecules & PubChem
Therapeutic considerations
Pregnancy cat.  ?
Legal status Schedule III (CA) Schedule I (US)
Routes Oral
 YesY(what is this?)  (verify)

Fenethylline, also spelled phenethylline, is a synthetic prodrug used as a stimulant and marketed under the brand name Captagon.

History

Fenethylline was invented in 1963 and used for around 25 years as a milder alternative to amphetamines. It was used in applications such as treating "hyperkinetic children" (what would now be referred to as Attention Deficit Hyperactivity Disorder), and also less commonly for treating narcolepsy or as an antidepressant. One of the main advantages of fenethylline was that it does not tend to increase blood pressure to the same extent as amphetamines and so could be used in patients with cardiovascular conditions.

Although fenethylline was considered to have fewer side effects and less potential for abuse than amphetamine, it nevertheless became illegal in most countries in 1986 after being listed by the World Health Organization for international scheduling under the Convention on Psychotropic Substances, even though the actual incidence of fenethylline abuse was quite low.

Pharmacology

Fenethylline is metabolized by the body to form two drugs amphetamine (24.5% of oral dose) and theophylline (13.7% of oral dose), both of which are active stimulants themselves. The physiological effects of fenethylline therefore result from a combination of all three drugs.

Abuse

Abuse of fenethylline as the brand Captagon is most common in Arab countries, and counterfeit versions of the legal drug continue to be available despite now being illegal for 20 years. Many of these counterfeit "Captagon" tablets actually contain other amphetamine derivatives that are easier to produce, but are pressed and stamped to look like Captagon pills. Some Captagon pills analyzed do contain fenethylline however, indicating that illicit production of this drug continues to take place.[1]

References

General
  • Kristen G, Schaefer A, von Schlichtegroll A. Fenethylline: therapeutic use, misuse and/or abuse. Drug and Alcohol Dependence. 1986 Jun;17(2-3):259-71.
  • Ellison T, Levy L, Bolger JW, Okun R. The metabolic fate of 3H-fenethylline in man. European Journal of Pharmacology 13:123, 1970.
  • United States. Drug Enforcement Administration. Forensic Sciences, Washington DC, 20537: DEA Microgram Bulletin. Mar. 2009.
Specific

 

The content of this section is licensed under the GNU Free Documentation License (local copy). It uses material from the Wikipedia article "Fenethylline" modified November 23, 2010 with previous authors listed in its history.