Definition and meaning of Fenethylline

Fenethylline

Systematic (IUPAC) name
(RS)-1,3-dimethyl- 7-[2-(1-phenylpropan-2-ylamino)ethyl]purine- 2,6-dione
Clinical data
AHFS/Drugs.com	International Drug Names
Pregnancy cat.	?
Legal status	Schedule III (CA) Schedule I (US)
Routes	Oral
Identifiers
CAS number	3736-08-1
ATC code	N06BA10
PubChem	CID 19527
DrugBank	DB01482
ChemSpider	18398 Y
UNII	YZ0N7VL5R3 Y
KEGG	D07944 Y
Chemical data
Formula	C18H23N5O2
Mol. mass	341.408 g/mol
SMILES O=C2N(c1ncn(c1C(=O)N2C)CCNC(C)Cc3ccccc3)C
InChI InChI=1S/C18H23N5O2/c1-13(11-14-7-5-4-6-8-14)19-9-10-23-12-20-16-15(23)17(24)22(3)18(25)21(16)2/h4-8,12-13,19H,9-11H2,1-3H3 Y Key:NMCHYWGKBADVMK-UHFFFAOYSA-N Y
Y (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 by Degussa AG in 1961^[1] and used for around 25 years as a milder alternative to amphetamines. Despite no accepted FDA indication for fenethylline, 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.

Fenethylline was considered to have fewer side effects and less potential for abuse than amphetamine. Nevertheless, fenethylline was listed in 1981 as a schedule I controlled substance in the US, and it 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.^[2] The physiological effects of fenethylline therefore result from a combination of all three drugs.^[3]

  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.^[4]

  References