Fenetylline

Structural formula
( R ) -form (top) and ( S ) -form (bottom), 1: 1 stereoisomeric mixture
General
Non-proprietary name	Fenetylline
other names	( RS ) -1,3-Dimethyl-7- [2- (1-phenylpropan-2-ylamino) ethyl] -3,7-dihydro-2 H -purine-2,6-dione ( IUPAC ) rac -1,3-dimethyl-7- [2- (1-phenylpropan-2-ylamino) ethyl] -3,7-dihydro-2 H -purine-2,6-dione DL -1,3-Dimethyl-7- [2- (1-phenylpropan-2-ylamino) ethyl] -3,7-dihydro-2 H -purine-2,6-dione Fenetyllinum ( Latin )
Molecular formula	C 18 H 23 N 5 O 2
External identifiers / databases
CAS number 3736-08-1 1892-80-4 fenetylline hydrochloride PubChem 102710 DrugBank DB01482 Wikidata Q415476
Drug information
ATC code	N06 BA10
Drug class	Amphetamine - derivative
Mechanism of action	Sympathomimetic
properties
Molar mass	341.41 g · mol -1
Melting point	227–229 ° C (fenetylline hydrochloride , racemate , polymorph 1 ) 237–239 ° C (fenetylline hydrochloride , racemate , polymorph 2 ) 246–247 ° C (fenetylline hydrochloride , L and D enantiomer )
solubility	almost insoluble in water, soluble in chloroform (fenetylline) soluble in water (fenetyllin hydrochloride)
safety instructions
Please note the exemption from the labeling requirement for drugs, medical devices, cosmetics, food and animal feed GHS hazard labeling no classification available
Toxicological data	100 mg kg −1 ( LD 50 ,  rat ,  oral )
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Fenetylline is a drug that is used as a sympathomimetic and stimulant . He was in traffic under the trade name Captagon .

The substance is one of the wake-up amines and has the phenylethylamine nucleus and the principal mechanism of action in common with the active ingredients amphetamine and methamphetamine . However, there are clear differences in metabolism .

Fenetylline is not available as a finished medicinal product in Germany. However, the Captagon drug , which was approved in Germany until 2003 , could be imported from abroad (Belgium) through international pharmacies until 2010. According to BtMG Annex III, fenetylline is a marketable narcotic drug that can be prescribed , but is practically unavailable due to the lack of an approved ready-to-use drug. Legally, it is the same as amphetamine.

History and use

Fenetylline was launched on the German pharmaceutical market in 1961 and used as an alternative to amphetamine for 25 years . Among other things, it was used for the drug treatment of ADHD , less common in narcolepsy or as an antidepressant , although the indication for amphetamines has changed frequently in the past. In the 1950s, fatigue or asthma were still an application area for these active ingredients.

The supply of fenetylline was subject to the BtMVV from 1972 . Since it was listed as dangerous drugs by UNODC in 1986 , it has been classified as an illicit narcotic drug in many countries . Fenetylline is on the World Anti-Doping Agency's prohibited list . In their laboratories, samples tested positive for fenetylline six times between 2003 and 2005.

During the Syrian civil war in 2013, the country advanced to become one of the largest producers and consumers of fenetylline in the region. In Syria, the stimulant was used to improve the performance of the fighters, while exports generated funds for the procurement of war equipment.

In Naples in July 2020, 14 tons (84 million pills) were tracked down, the largest drug delivery to date of fenetylline, which was produced in Syria by members of the al-Assad family in the course of the Syrian civil war and exported from Latakia via the seaport .

effect

Like amphetamine , fenetylline penetrates the blood-brain barrier and then triggers a cascade of catecholaminergic effects in the central nervous system (CNS). There are also sympathomimetic effects on the cardiovascular system .

Fenetylline is converted by the body into two independently active stimulants: amphetamine (24.5% of the oral dose) and theophylline (13.7% of the oral dose).

The effects on the CNS include a change in the dopaminergic and noradrenergic metabolism of the brain , similar to the drug methylphenidate , which has a similar effect . According to current research, it is assumed that the reduction in dopamine transport density (DAT) on the corpus striatum results in a higher dopamine concentration at the synaptic gap, in short, the dopamine concentration is increased in parts of the brain. In particular, this takes place in the prefrontal cortex (frontal lobe). This leads to the typical amphetamine effects such as increased alertness , motivation and others.

abuse

When overdosing on fenetylline, large amounts of the neurotransmitters norepinephrine and dopamine are released from the storage vesicles in the central nervous system . This can lead to convulsions , cardiovascular breakdown, and emergency psychiatric states . As a rule, the application is carried out orally . As with other active ingredients of this type, other forms of application are also used, some of which involve extreme risks, as described below.

The durable, high-dose, improper administration of fenetylline leads as the high dose, lasting for a similar image, improper administration of methamphetamine (usually in impure form as a street drug Crystal meth known) in nasal or rectal , or intravenous administration.

In particular, these are the attack on (autonomous) reserves of the body, the consumption of energy reserves ( fat , muscle tissue ), the gradual breakdown of personality / consciousness . This is mainly due to a lack of sleep (for several weeks), the significantly increased energy requirement, which, however, is not covered by the very strong appetite inhibition and the lack of food intake and the extremely rapid consumption of vital substances such as vitamins . Such extreme abuse of amphetamine-like active ingredients can therefore lead to death within a few weeks.

An acute overdose can lead to sudden cardiac death in pre-existing cardiovascular diseases , especially if the overdose is combined with high physical exertion.

In other cases, dehydration can result in death after cardiovascular failure , when extreme physical stress over several hours and high or often repeated use of the active ingredient come together (e.g. in the discotheque).

doping

The Bundesliga coach Peter Neururer described doping with Captagon in football as "common practice" in the late 1980s. “I know that Captagon was previously used. Many players were crazy about it, "Neururer is quoted as saying:" It was known everywhere and was practiced. Up to 50 percent have consumed it. Not just in the second division. "

The then national goalkeeper Toni Schumacher also reported on the abuse of Captagon in his book Anpfiff in 1987 . In August 2013 Dieter Schatzschneider also confirmed such doping practices in West German professional football.

In 2015, the former Austrian national soccer player Werner Kriess reported on the widespread use of Captagon in the 1970s when he was active at FC Wacker Innsbruck .

Individual evidence

1. ↑ ^{a b c} Entry on fenetylline. In: Römpp Online . Georg Thieme Verlag, accessed on June 19, 2014.
2. ↑ ^{a b} Merck Index , 9th edition. Merck & Co., 1976, ISBN 0-911910-26-3 , p. 519.
3. ↑ ^{a b} xiuzhengrd.com: Fenetylline: Clarke's Analysis of Drugs and Poisons ( Memento of the original from January 1, 2016 in the Internet Archive ) Info: The archive link was inserted automatically and has not yet been checked. Please check the original and archive link according to the instructions and then remove this notice. , accessed January 1, 2016. 
4. ↑ This substance has either not yet been classified with regard to its hazardousness or a reliable and citable source has not yet been found.
5. ↑ Entry on fenetylline in the ChemIDplus database of the United States National Library of Medicine (NLM) .
6. ↑ Ernst Mutschler u. a .: Mutschler drug effects: textbook of pharmacology and toxicology . Knowledge Verlag-Ges. 2001. ISBN 978-3-8047-1763-3 .
7. ^ Neuro-psychotropic drugs by Riederer / Laux / Pöldinger, Volume 1 (1992): Timeline for the introduction of various psychotropic drugs
8. ↑ DRUGS: Controversial p . Der Spiegel 8/1982, accessed on June 4, 2016.
9. ↑ Michèle Binswanger : The doping of the terrorists. In: Tages-Anzeiger Zurich / Newsnet . November 24, 2015.
10. ^ Amphetamine smuggling in Syria . n-tv.de, March 19, 2016. Accessed June 4, 2016.
11. ↑ Christoph Reuter, DER SPIEGEL: Italy: Has the Islamic State smuggled 14 tons of Capatgon tablets? - DER SPIEGEL - Politics. Retrieved July 3, 2020 . 
12. ↑ Theodore Ellison et al. (1970): The metabolic fate of 3H-fenethylline in man. In: European Journal of Pharmacology. 13, p. 123. doi : 10.1016 / 0014-2999 (70) 90192-5 .
13. ↑ Bernd Nickel et al. (1986): Fenetylline: New results on pharmacology, metabolism and kinetics . In: Drug and Alcohol Dependence . tape 17 , no. 2-3 , p. 235-257 , doi : 10.1016 / 0376-8716 (86) 90011-6 ( researchgate.net ).
14. ^ Johanna Krause , Klaus-Henning Krause : ADHD in adulthood. Schattauer 2014, ISBN 978-3-7945-2782-3 .
15. ↑ Gerfried Kristen, Annelies Schaefer (1986): Fenetylline: Therapeutic use, misuse and / or abuse . In: Drug and Alcohol Dependence . tape 17 , no. 2-3 , p. 259-271 , doi : 10.1016 / 0376-8716 (86) 90012-8 .
16. ↑ Peter Neururer: Doping in football was "common practice". In: sueddeutsche.de . May 17, 2010, accessed April 15, 2015 . 
17. ↑ Toni Schumacher: I felt like cattle for slaughter . In: Der Spiegel . No. 9 , 1987, pp. 196-198 ( online ).
18. ↑ Dieter Schatzschneider: "We also doped" . ndr.de, August 22, 2013, accessed June 4, 2016.
19. ↑ Five years ago today: The doping confession of the ÖFB team captain (April 19, 2020)

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