Fenetylline

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Fenethylline
Clinical data
AHFS/Drugs.com	International Drug Names
Routes of; administration	Oral
ATC code	N06BA10 (WHO) ;
Legal status
Legal status	CA: Schedule III ; US: Schedule I ;
Identifiers
	IUPAC name (RS)-1,3-dimethyl- 7-[2-(1-phenylpropan-2-ylamino)ethyl]purine- 2,6-dione;
CAS Number	3736-08-1 ;
PubChem CID	19527;
DrugBank	DB01482 ;
ChemSpider	18398 ;
UNII	YZ0N7VL5R3;
KEGG	D07944 ;
E number	{{#property:P628}}
ECHA InfoCard	{{#property:P2566}}Lua error in Module:EditAtWikidata at line 36: attempt to index field 'wikibase' (a nil value).
Chemical and physical data
Formula	C18H23N5O2
Molar mass	341.408 g/mol
3D model (JSmol)	Interactive image;
	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 ; Key:NMCHYWGKBADVMK-UHFFFAOYSA-N ;
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Editor-In-Chief: C. Michael Gibson, M.S., M.D. [1]

Overview

Fenethylline (BAN, USAN), also spelled phenethylline and fenetylline (INN), and also known as amphetaminoethyltheophylline and amfetyline, is a chemical linkage of amphetamine and theophylline which behaves as a prodrug to both of the aforementioned drugs.^[1]^[2] It is marketed for use as a psychostimulant under the brand names Captagon, Biocapton, and Fitton.^[1]^[2]

History

Fenethylline was invented by Degussa AG in 1961^[3] 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.^[4] The physiological effects of fenethylline therefore result from a combination of all three drugs.^[5]

Abuse

Abuse of fenethylline of the brand name Captagon is most common in Arab countries and counterfeit versions of the drug continue to be available despite its illegality.^[6] ^[7]

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 counterfeit Captagon pills analyzed do contain fenethylline however, indicating that illicit production of this drug continues to take place.^{[citation needed]}

Fenethylline is a popular drug, allegedly used by militant groups in Syria and Lebanon. It is manufactured locally in a cheap and simple process. According to some leaks, militant groups would also export the drug in exchange for weapons and cash.^[8]^[9]

References

↑ ^1.0 ^1.1 Dictionary of Organic Compounds. CRC Press. pp. 3140–. ISBN 978-0-412-54090-5.
↑ ^2.0 ^2.1 Index Nominum 2000: International Drug Directory. Taylor & Francis. January 2000. pp. 431–. ISBN 978-3-88763-075-1.
↑ Fenetylline: therapeutic use, misuse and/or abuse. Kristen G, Schaefer A, von Schlichtegroll A. Drug 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.
↑ Chemical characterization of counterfeit captagon tablets seized in Jordan. Alabdalla MA. Forensic Science International. 2005 Sep 10;152(2-3):185-8.
↑ "2011 Global Assessment of Amphetamine-Type Stimulants" (PDF). United Nations Office on Drugs and Crime.
↑ "Le Captagon®, arme principale des jihadistes". Reseau Voltaire.
↑ Colin Freeman (2014-01-12). "Syria's civil war being fought with fighters high on drugs". The Telegraph. Retrieved 2014-01-13.
↑ Stephen Kalin (2014-01-12). "Insight: War turns Syria into major amphetamines producer, consumer". Reuters. Retrieved 2014-04-21.

Template:Stimulants

[Buckingham1995-1] 1.0 ^1.1 Dictionary of Organic Compounds. CRC Press. pp. 3140–. ISBN 978-0-412-54090-5.

[IndexNominum2000-2] 2.0 ^2.1 Index Nominum 2000: International Drug Directory. Taylor & Francis. January 2000. pp. 431–. ISBN 978-3-88763-075-1.

[misuse-3] Fenetylline: therapeutic use, misuse and/or abuse. Kristen G, Schaefer A, von Schlichtegroll A. Drug Alcohol Dependence. 1986 Jun;17(2-3):259-71.

[4] Ellison T, Levy L, Bolger JW, Okun R. The metabolic fate of 3H-fenethylline in man. European Journal of Pharmacology 13:123, 1970.

[5] Chemical characterization of counterfeit captagon tablets seized in Jordan. Alabdalla MA. Forensic Science International. 2005 Sep 10;152(2-3):185-8.

[6] "2011 Global Assessment of Amphetamine-Type Stimulants" (PDF). United Nations Office on Drugs and Crime.

[7] "Le Captagon®, arme principale des jihadistes". Reseau Voltaire.

[8] Colin Freeman (2014-01-12). "Syria's civil war being fought with fighters high on drugs". The Telegraph. Retrieved 2014-01-13.

[9] Stephen Kalin (2014-01-12). "Insight: War turns Syria into major amphetamines producer, consumer". Reuters. Retrieved 2014-04-21.

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