Chemistry:Fenethylline

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Short description: Codrug of amphetamine and theophylline
Fenethylline
INN: Fenetylline
Skeletal formula
Space-filling model of the captagon molecule
Clinical data
AHFS/Drugs.comInternational Drug Names
Routes of
administration		Oral
ATC code
Legal status
Legal status
Identifiers
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
Chemical and physical data
FormulaC18H23N5O2
Molar mass341.415 g·mol−1
3D model (JSmol)
ChiralityRacemic mixture
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Fenethylline (BAN, USAN) is a codrug of amphetamine and theophylline and a prodrug to both. It is also spelled phenethylline and fenetylline (INN); other names for it are amphetamin​oethyl​theophylline and amfetyline. The drug was marketed for use as a psychostimulant under the brand names Captagon, Biocapton, and Fitton.[1][2] It is now illegal in most countries and is produced primarily for illicit use. Syria is considered to be the world's largest producer of the drug, accounting for about 80% of the global supply.[3][4]

History

Fenethylline was first synthesized by the German pharmaceutical firm Degussa AG in 1961 and used for around 25 years as a milder alternative to amphetamine and related compounds.[5] Although there are no FDA-approved indications for fenethylline, it was used in the treatment of "hyperkinetic children", in what would now be called attention deficit hyperactivity disorder, and, less commonly, for narcolepsy and depression. One of the main advantages of fenethylline was that it does not increase blood pressure to the same extent as an equivalent dose of amphetamine and so could be used in patients with cardiovascular conditions.[6]

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 United States, 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.[6][circular reference]

Pharmacology

The fenethylline molecule results when theophylline is covalently linked with amphetamine by an alkyl chain.[7]

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. The physiological effects of fenethylline therefore seem to result from a combination of these two compounds,[8][9][10] although how is not entirely clear, and seems to involve a synergistic effect between amphetamine and theophylline produced following metabolism.[6][11] The pharmacological actions of fenethylline before cleavage also remain poorly established, though it appears to act directly at several serotonin receptors.[12]

Abuse and illegal trade

Abuse of fenethylline of the brand name Captagon is common in the Middle East,[13][14] and counterfeit versions of the drug continue to be available despite its illegality.[15][16] Captagon is much less common outside of the Middle East, to the point that police may not recognize the drug. Captagon production and export has become a big industry sponsored by the Syrian government, with revenue from its exports contributing to more than 90% of its foreign currency.[17] The Assad regime's annual Captagon merchandise is estimated to have been worth United States dollar 57 billion in 2022, about three times the total trade of all Mexican drug barons.[18][19][3]

Many of these counterfeit "Captagon" tablets contain other amphetamine derivatives that are easier to produce, but are pressed and stamped to look like Captagon pills. Some counterfeit Captagon pills analysed do contain fenethylline, indicating that illicit production of this drug continues to take place.[20] These illicit pills often contain "a mix of amphetamines, caffeine[,] and various fillers", which are sometimes referred to as "captagon" (with a lowercase "c").

Fenethylline is a popular drug in Western Asia, and American media outlet CNN reported in 2015 that it is allegedly used by militant groups in Syria.[21] Later research demonstrated that it was the Syrian government of Bashar al-Assad that has been financing Captagon production and sponsoring networks of its drug dealers in coordination with the Syrian intelligence.[22] It is manufactured locally by a cheap and simple process. In July 2019 in Lebanon, captagon was sold for $1.50 to $2.00 a pill.[23] In 2021 in Syria, low-quality pills were sold locally for less than $1, while high-quality pills are increasingly smuggled abroad and may cost upwards of $14 each in Saudi Arabia.[13]

According to some leaks, militant groups export the drug in exchange for weapons and cash.[24][25] According to Abdelelah Mohammed Al-Sharif, secretary general of the National Committee for Narcotics Control and assistant director of Anti-Drug and Preventative Affairs, forty percent of users between the ages of twelve and twenty-two in Saudi Arabia are addicted to fenethylline.[26] Hamas terrorists who participated in Operation Al-Aqsa Flood, and in the subsequent massacres of Israeli citizens, in the Re'im music festival massacre and in the Sexual and gender-based violence in the 7 October attack on Israel, the casus belli of the 2023 Israel–Hamas War, had reportedly allegedly taken Captagon.[27]

Increasing usage and seizures

According to United Nations Office on Drugs and Crime (UNODC), Saudi Arabia received seven tonnes of Captagon in 2010, a third of the world supply.[28] In 2017, Captagon was the most popular recreational drug in the Arabian Peninsula.[29]

In October 2015, a member of the Saudi royal family, Prince Abdel Mohsen Bin Walid Bin Abdulaziz, and four others were detained in Beirut on charges of drug trafficking after airport security discovered two tons of Captagon (fenethylline) pills and some cocaine on a private jet scheduled to depart for Riyadh, the Saudi capital.[30][31][32] The following month, Agence France-Presse reported that the Turkish authorities had seized two tonnes of Captagon — about eleven million pills — during raids in the Hatay region on the Syrian border. The pills had been produced in Syria and were being shipped to countries in the Arab states of the Persian Gulf.[33]

In December 2015, the Lebanese Army announced that it had discovered two large-scale drug production workshops in the north of the country and seized large quantities of Captagon pills. Two days earlier, three tons of Captagon and hashish were seized at Beirut Airport, concealed in school desks being exported to Egypt.[34]

References to the drug were found on a mobile phone used by Mohamed Lahouaiej Bouhlel, a French-Tunisian who killed eighty-four civilians in Nice on Bastille Day 2016.[35]

In May 2017, French customs at Charles de Gaulle Airport seized 750,000 Captagon pills being transported from Lebanon to Saudi Arabia.[36] In 2017, two other consignments of pills were found at Charles de Gaulle Airport: in January, heading for the Czech Republic, and in February, hidden in steel moulds.[37] Further investigation showed that the seized products mainly contained a mixture of amphetamine and theophylline.[38]

In January 2018, Saudi Arabia seized 1.3 million Captagon pills at the Al-Haditha crossing near the border with Jordan.[39] In December 2018, Greece intercepted a Syrian ship sailing for Libya, carrying six tonnes of processed cannabis and three million Captagon pills.[40] In July 2019, a shipment of thirty-three million Captagon pills, weighing 5.25 tonnes, was seized in Greece coming from Syria.[41] In July 2019, eight hundred thousand Captagon pills were found on a boat in the United Arab Emirates.[42] In August 2019, Saudi customs at Al-Haditha seized 2,579,000 Captagon pills found inside a truck and a private vehicle.[43]

In February 2020, the UAE found thirty-five million Captagon pills in a shipment of electric cables from Syria to Jebel Ali.[44] In April 2020, Saudi Arabia seized 44.7 million Captagon pills smuggled from Syria,[45] and citing drug smuggling concerns, imposed an import ban on fruits and vegetables from Lebanon, causing the price of Lebanese lettuce to plummet.[46][47] On 1 July 2020, an anti-drug operation coordinated in Italy by the Italian Guardia di Finanza and Customs and Monopolies Agency seized fourteen tonnes of amphetamines, labeled as Captagon, smuggled from Syria and initially thought by the Italian authorities to have been produced by ISIS,[48][49][50] which were found in three shipping containers filled with around 84 million pills, in the southern port of Salerno.[48][49][50][51]

In November 2020, Egypt seized two shipments of Captagon pills at Damietta port coming from Syria. The first had 3,251,500 tablets,[52] while the second contained 11 million tablets.[53] In December 2020, Italian authorities seized about 14 tonnes of Captagon arriving from Latakia, Syria, and heading towards Libya, numbering about 85 million pills, worth around $1 billion.[54]

In January 2021, Egyptian authorities seized eight tons of Captagon and another eight tons of hashish at Port Said, from a shipment that arrived from Lebanon.[55] In February 2021, Lebanese customs seized at Beirut port a shipment of 5 million Captagon pills hidden in a tile-making machine, intended for Greece and Saudi Arabia.[56] In April 2021, Saudi authorities discovered 5.3 million Captagon pills hidden in fruits imported from Lebanon.[57]

Production in Syria

127 bags of Captagon seized in Syria before being destroyed in May 2018

The drug is playing a role in the Syrian civil war.[58][59] The production and sale of fenethylline generates large revenues which are likely used to fund weapons, and fenethylline is used as a stimulant by combatants.[59][60][61] Poverty and international sanctions that limit legal exports are contributing factors.[62]

In May 2021, the UK newspaper The Guardian described the effects of Captagon production in Syria on the economy as a dirty business that is creating a near-narco-state. Drug money flowing into Syria is destabilizing legitimate businesses, positioning it as the global centre of Captagon production, with increased industrialization, adaptation, and technical sophistication.[63] In June 2021, Saudi authorities at Jeddah port seized fourteen million Captagon tablets hidden inside a shipment of iron plates coming from Lebanon.[64] In the same month, Saudi authorities seized a shipment of 4.5 million Captagon pills, smuggled inside several orange cartons, at Jeddah port.[65] In July 2021, Saudi customs discovered 2.1 million Captagon pills at Al-Haditha hidden in a tomato paste shipment.[66]

The New York Times reported in December 2021 that the Syrian Army's elite 4th Armoured Division, commanded by Maher al-Assad, whose brother Bashar al-Assad is the ruler of Syria, oversees much of the production and distribution of Captagon, among other drugs. The unit controls manufacturing facilities, packing plants, and smuggling networks all across Syria, and had started to deal in crystal meth.[13] The division's security bureau, headed by Maj. Gen. Ghassan Bilal, provides protection for factories and along smuggling routes to the port city Latakia and to border crossings with Jordan and Lebanon. Jihad Yazigi, editor of The Syria Report, reported that Captagon "has probably become Syria's most important source of foreign currency."[13]

Synthesis

Reaction sequence

Synthesis of fenethylline:[67][68][69]

Theophylline (1) is alkylated using 2-bromochloroethane (2) in a substitution reaction to give 7-(2-Chloroethyl)theophylline (aka Benaphyllin, Eupnophile) (3). 7-(2-Chloroethyl)theophylline forms a three-carbon ring substructure by displacing the remaining halogen leaving group in an intramolecular substitution reaction. The three-carbon ring substructure is deformed by the primary amine in amphetamine (4), giving fenethylline (5).[69]

Reaction conditions

Theophylline (1) is allowed to react with 2-bromochloroethane (2) by refluxing both compounds at 90 °C for 18h. The produced 7-(2-Chloroethyl)theophylline (3) is filtered and purified. After purification, compound 3 is mixed with amphetamine (4) in a mixture at 100 °C for 17 hours to produce fenethylline (5).[69]

Compound identification

Since fenethylline is a highly controlled drug, a variety of identification methods are needed in order to regulate it. Many identification methods with different samples have been tested. Gas chromatography-mass spectrometry (GC-MS) has been proven as an accurate tool to identify fenethylline in solid samples, as well as in urine and hair samples.[70]

See also

References

  1. ↑ Dictionary of Organic Compounds. CRC Press. 1996. pp. 3140–. ISBN 978-0-412-54090-5. https://books.google.com/books?id=x2Su3GKCvtsC&pg=PA3140. 
  2. ↑ Index Nominum 2000: International Drug Directory. Taylor & Francis. 2000. pp. 431–. ISBN 978-3-88763-075-1. https://books.google.com/books?id=5GpcTQD_L2oC&pg=PA431. 
  3. ↑ 3.0 3.1 "A little-known drug brought billions to Syria's coffers. Now it's a bargaining chip". CNN. 11 April 2023. https://edition.cnn.com/2023/04/10/middleeast/syria-drugs-bargaining-chip-mime-intl/index.html. 
  4. ↑ "What is Captagon, the addictive drug mass-produced in Syria?". Al Jazeera News. 9 May 2023. https://www.aljazeera.com/news/2023/5/9/what-is-captagon-the-addictive-drug-mass-produced-in-syria. 
  5. ↑ "Fenetylline: therapeutic use, misuse and/or abuse". Drug and Alcohol Dependence 17 (2–3): 259–271. June 1986. doi:10.1016/0376-8716(86)90012-8. PMID 3743408. 
  6. ↑ 6.0 6.1 6.2 "Fenethylline (Captagon) Abuse - Local Problems from an Old Drug Become Universal". Basic & Clinical Pharmacology & Toxicology 119 (2): 133–140. August 2016. doi:10.1111/bcpt.12584. PMID 27004621. 
  7. ↑ "Fenetylline: new results on pharmacology, metabolism and kinetics". Drug and Alcohol Dependence 17 (2–3): 235–257. June 1986. doi:10.1016/0376-8716(86)90011-6. PMID 3743407. 
  8. ↑ "The metabolic fate of 3H-fenetylline in man". European Journal of Pharmacology 13 (1): 123–128. 1970. doi:10.1016/0014-2999(70)90192-5. PMID 5496920. 
  9. ↑ "Chemical characterization of counterfeit captagon tablets seized in Jordan". Forensic Science International 152 (2–3): 185–188. September 2005. doi:10.1016/j.forsciint.2004.08.004. PMID 15978343. 
  10. ↑ "Vaccine-driven pharmacodynamic dissection and mitigation of fenethylline psychoactivity". Nature 548 (7668): 476–479. August 2017. doi:10.1038/nature23464. PMID 28813419. Bibcode: 2017Natur.548..476W. 
  11. ↑ "Insight of Captagon Abuse by Chemogenomics Knowledgebase-guided Systems Pharmacology Target Mapping Analyses". Scientific Reports 9 (1): 2268. February 2019. doi:10.1038/s41598-018-35449-6. PMID 30783122. 
  12. ↑ "Structural insight into the serotonin (5-HT) receptor family by molecular docking, molecular dynamics simulation and systems pharmacology analysis". Acta Pharmacologica Sinica 40 (9): 1138–1156. September 2019. doi:10.1038/s41401-019-0217-9. PMID 30814658. 
  13. ↑ 13.0 13.1 13.2 13.3 "On Syria's Ruins, a Drug Empire Flourishes". The New York Times. 5 December 2021. ISSN 0362-4331. https://www.nytimes.com/2021/12/05/world/middleeast/syria-drugs-captagon-assad.html. 
  14. ↑ "Middle East's drug of choice" (in en). 2023-07-01. https://mondediplo.com/2023/07/03captagon. 
  15. ↑ "2011 Global Assessment of Amphetamine-Type Stimulants". United Nations Office on Drugs and Crime. http://www.unodc.org/documents/southeastasiaandpacific/2011/09/global-ats-2011/ATS_Global_Assessment_2011_web.pdf. 
  16. ↑ "Why would the Islamic State group try to smuggle the 'drug of the Jihad' into Europe?". 2 July 2020. https://www.abc.net.au/news/2020-07-02/italy-drug-bust-captagon-how-is-it-linked-to-islamic-state/12414804. 
  17. ↑ "How Syria became the world's most profitable narco state". The Spectator. 19 November 2022. https://www.spectator.co.uk/article/how-syria-became-the-worlds-most-profitable-narco-state/. 
  18. ↑ "Assad cousins hit with sanctions over amphetamine trade that funds regime". Financial Times. 28 March 2023. https://www.ft.com/content/de522480-4738-49fb-985e-c0e1538846ff. 
  19. ↑ "Tackling the illicit drug trade fuelling Assad's war machine". 28 March 2023. https://www.gov.uk/government/news/tackling-the-illicit-drug-trade-fuelling-assads-war-machine. 
  20. ↑ "Study of Adulterants and Diluents in Some Seized Captagon-Type Stimulants.". Annals of Clinical Nutrition (MedDocs Publishers) 3 (1): 1017. 2020. https://meddocsonline.org/annals-of-clinical-nutrition/study-of-adulterants-and-diluents-in-some-seized-captagon-type-stimulants.pdf. 
  21. ↑ "Syria fighters may be fueled by amphetamines". CNN. 21 November 2015. http://www.cnn.com/2015/11/20/world/syria-fighters-amphetamine/index.html. 
  22. ↑ "The Syrian Economy at War: Captagon, Hashish, and the Syrian Narco-State". 27 April 2021. https://coar-global.org/2021/04/27/the-syrian-economy-at-war-captagon-hashish-and-the-syrian-narco-state/. "Whereas attention has been lavished on drug use among combatants, little attention has been paid to the societal and individual costs of the pervasive spread of narcotics during the conflict. Even more neglected are the structural dynamics of drug trafficking and their impact on the trajectory of the conflict itself. As the Syrian state has re-consolidated control over much of the country since 2018, narcotics trafficking in Syria has become more expansive and widespread. In parallel, the decimation of conventional economic activities has increased the relative attractiveness of industrial-scale drug profiteering, which has been largely captured and controlled by narco-entrepreneurs linked to the regime of Syrian President Bashar al-Assad and the regime's foreign allies. Ironically, the armed group commonly thought to be most closely associated with the Captagon trade — Islamic State — is, in fact, among the few conflict actors that has had no demonstrable institutional connection to the trade of this drug. This association has persisted in large part because of sensational foreign media coverage. the narcotics trade was decisively reconfigured to the advantage of pro-Government forces. Increasingly prominent in this period are narco-entrepreneurs affiliated with the Assad regime. Record-setting foreign drug interceptions since 2018 evince the evolution of Syria's drug industry, with exports of Captagon and hashish suggesting new levels of mass production." 
  23. ↑ "The tiny pill fueling Syria's war and turning fighters into superhuman soldiers". The Washington Post. 19 November 2015. https://www.washingtonpost.com/news/worldviews/wp/2015/11/19/the-tiny-pill-fueling-syrias-war-and-turning-fighters-into-super-human-soldiers/?tid=pm_pop_b. 
  24. ↑ "Syria's civil war being fought with fighters high on drugs". The Telegraph. 12 January 2014. https://www.telegraph.co.uk/news/worldnews/middleeast/syria/10567021/Syrias-civil-war-being-fought-with-fighters-high-on-drugs.html. 
  25. ↑ "Insight: War turns Syria into major amphetamines producer, consumer". Reuters. 12 January 2014. https://www.reuters.com/article/us-syria-crisis-drugs-insight-idUSBREA0B04H20140112. 
  26. ↑ "40% of young Saudi drug addicts taking Captagon". Arab News (Jeddah, Saudi Arabia). 28 October 2015. http://www.arabnews.com/saudi-arabia/news/826906. 
  27. ↑ "High on Captagon and Antisemitism: Everything About 'The ISIS Drug' Used by Hamas". Haaretz. https://www.haaretz.com/israel-news/2023-11-21/ty-article-magazine/.premium/high-on-captagon-and-antisemitism-everything-about-the-isis-drug-used-by-hamas/0000018b-f230-d558-a3eb-f73face80000. 
  28. ↑ "Insight - War turns Syria into major amphetamines producer, consumer". Reuters. 13 January 2014. https://www.reuters.com/article/uk-syria-crisis-drugs-idUKBREA0B04K20140113?edition-redirect=uk. 
  29. ↑ "A new drug of choice in the Gulf". The Economist. 18 July 2017. https://www.economist.com/news/middle-east-and-africa/21725167-dangerous-arrival-dangerous-region-new-drug-choice-gulf. 
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  32. ↑ "Saudi Royal, Four Others Detained in Beirut Captagon Bust". NBC News. 26 October 2015. https://www.nbcnews.com/news/world/saudi-royal-four-others-detained-beirut-captagon-bust-n451486. 
  33. ↑ "Turkey seizes 11 million pills of 'Syria war drug': Reports". Agence France-Presse (Istanbul). 20 November 2015. http://timesofindia.indiatimes.com/world/middle-east/Turkey-seizes-11-million-pills-of-Syria-war-drug-reports/articleshow/49860478.cms. 
  34. ↑ The Daily Star (Lebanon): Tuesday raids in east Lebanon netted 800 kg of hash:police and Lebanese Army busts two drug factories
  35. ↑ "Attacker in Nice plotted for months with 'accomplices'". CNN. 21 July 2016. http://www.cnn.com/2016/07/21/europe/nice-france-attacker-plot-accomplices/index.html. 
  36. ↑ "In a first, authorities say they found 750,000 'Captagon' pills in France". The Washington Post. 30 May 2017. https://www.washingtonpost.com/news/worldviews/wp/2017/05/30/in-a-first-authorities-say-they-found-750000-captagon-pills-in-france/. 
  37. ↑ "Customs seize 135 kg of captagon for first time in France". 30 May 2017. http://www.rfi.fr/en/france/20170530-jihadist-drug-captagon-seized-first-time-france. 
  38. ↑ "Les 135 kilos de drogue saisis n'étaient pas du Captagon, "la drogue des djihadistes"". Le Parisien. 2017. https://www.leparisien.fr/faits-divers/les-135-kilos-de-drogue-saisis-n-etaient-pas-du-captagon-la-drogue-des-djihadistes-06-06-2017-7022343.php. 
  39. ↑ "Saudi customs bust drug smugglers with haul of 1.3m pills". 12 January 2018. https://www.arabnews.com/node/1224416/saudi-arabia. 
  40. ↑ "Greece seizes big drugs haul from Syrian freighter sailing for Libya". London: Reuters. 14 December 2018. https://www.reuters.com/article/us-greece-drugs/greece-seizes-big-drugs-haul-from-syrian-freighter-sailing-for-libya-idUSKBN1OD1RF. 
  41. ↑ "Greece seizes record amount of amphetamine Captagon shipped from Syria". London: Reuters. 5 July 2019. https://www.reuters.com/article/us-greece-drugs/greece-seizes-record-amount-of-amphetamine-captagon-shipped-from-syria-idUSKCN1U01IH. 
  42. ↑ "Dogs help seize 800,000 Captagon pills worth Dh3 million". 24 July 2019. https://gulfnews.com/uae/dogs-help-seize-800000-captagon-pills-worth-dh3-million-1.65412113. 
  43. ↑ "Saudi officials stop Captagon smuggling plots". 21 August 2019. https://www.arabianbusiness.com/culture-society/426154-saudi-officials-stop-captagon-smuggling-plots. 
  44. ↑ "Video: Massive drug bust in Dubai, 5.6 tonnes of captagon seized". 26 February 2020. https://www.khaleejtimes.com/uae/dubai/video-massive-drug-bust-in-dubai-56-tonnes-of-captagon-seized. 
  45. ↑ "Saudi Arabia busts drug smuggling operation from Assad's Syria". 30 April 2020. https://www.middleeastmonitor.com/20200430-saudi-arabia-busts-drug-smuggling-operation-from-assads-syria/. 
  46. ↑ "Saudi Arabia bans fruit, vegetable imports from Lebanon". https://www.aa.com.tr/en/middle-east/saudi-arabia-bans-fruit-vegetable-imports-from-lebanon/2218829. 
  47. ↑ "Lebanese fear fruit and vegetables going to waste with Saudi market shut". Reuters. 12 May 2021. https://www.reuters.com/world/middle-east/lebanese-fear-fruit-vegetables-going-waste-with-saudi-market-shut-2021-05-12/. 
  48. ↑ 48.0 48.1 "Salerno, sequestrate 84 milioni di pasticche di droga dell'Isis: le stesse usate dai terroristi del Bataclan" (in it). La Repubblica (Rome). 1 July 2020. https://napoli.repubblica.it/cronaca/2020/07/01/news/salerno_sequestrate_14_tonnellate_di_droga_dell_isis_valgono_un_miliardo-260651827/. ; ""La droga dell'Isis non-era dell'Isis": quelle 14 tonnellate di anfetamine sequestrate in Italia e il legame con la Siria di Assad" (in it). La Repubblica (Rome). 10 July 2020. https://rep.repubblica.it/pwa/generale/2020/07/10/news/la_droga_dell_isis_non_era_dell_isis_quelle_14_tonnellate_di_anfetamine_sequestrate_in_italia_e_il_legame_con_la_siria_di-261584585/. 
  49. ↑ 49.0 49.1 "Italian police seize 14 tons of amphetamines with possible ISIS link". London: NBC News. 1 July 2020. https://www.nbcnews.com/news/world/italian-police-seize-14-tons-amphetamines-possible-isis-link-n1232633. 
  50. ↑ 50.0 50.1 "Italian Police on Amalfi Coast Seize 84 Million 'Captagon' Pills Shipped by ISIS From Syria". The Daily Beast. 1 July 2020. https://www.thedailybeast.com/italian-police-on-amalfi-coast-seize-84-million-captagon-pills-shipped-by-isis-from-syria. 
  51. ↑ "Captagon: Italy seizes €1bn of amphetamines 'made to fund IS'". BBC News. 1 July 2020. https://www.bbc.com/news/world-europe-53254879. 
  52. ↑ "Egyptian police seize container with 1,858 Captagon drug packets". 15 November 2020. https://egyptindependent.com/managed-to-seize-a-container-police-seizes-container-containing-1858-packets-of-captagon-drug-hidden-in-canned-corn-shipmentcontaining-1858-packets-of-captagon-drug-hidden-in-canned-corn-shipment/. 
  53. ↑ "Attempt to smuggle 11M drug tablets in container thwarted". 30 November 2020. https://www.egypttoday.com/Article/1/94822/Attempt-to-smuggle-11M-drug-tablets-in-container-thwarted. 
  54. ↑ "Captagon: Destroying the frontline drug". BBC News. 21 December 2020. https://www.bbc.com/news/av/world-55378461. 
  55. ↑ "Egypt busts massive drugs haul worth Dh143m". 6 January 2021. https://gulfnews.com/world/mena/egypt-busts-massive-drugs-haul-worth-dh143m-1.76292594. 
  56. ↑ "Lebanon seizes 5m captagon pills at Beirut port". 3 February 2021. https://www.arabnews.com/node/1803386/middle-east. 
  57. ↑ "Lebanon vows to punish drug smugglers as Saudi import ban bites". 25 April 2021. https://www.arabnews.com/node/1848171/middle-east. 
  58. ↑ "Captagon, ISIS's favorite amphetamine, explained". 20 November 2015. https://www.vox.com/world/2015/11/20/9769264/captagon-isis-drug. 
  59. ↑ 59.0 59.1 "Captagon: the amphetamine fuelling Syria's civil war". The Guardian. 13 January 2014. https://www.theguardian.com/world/shortcuts/2014/jan/13/captagon-amphetamine-syria-war-middle-east. 
  60. ↑ "Insight – War turns Syria into major amphetamines producer, consumer" (in en-GB). Reuters. http://uk.reuters.com/article/uk-syria-crisis-drugs-idUKBREA0B04K20140113. 
  61. ↑ "Syria's Breaking Bad: Are Amphetamines Funding the War?". Time. ISSN 0040-781X. http://world.time.com/2013/10/28/syrias-breaking-bad-are-amphetamines-funding-the-war/. Retrieved 2016-02-03. 
  62. ↑ "The Arab World's New Drug of Choice". 4 June 2022. https://www.bbc.co.uk/programmes/m00180hs. 
  63. ↑ "'A dirty business': how one drug is turning Syria into a narco-state". 7 May 2021. https://www.theguardian.com/world/2021/may/07/drug-captagon-turning-syria-into-narco-state. 
  64. ↑ "14 million Captagon amphetamine pills coming from Lebanon seized". 26 June 2021. https://saudigazette.com.sa/article/608191/SAUDI-ARABIA/14-million-Captagon-amphetamine-pills-coming-from-Lebanon-seized. 
  65. ↑ "Saudi Arabia seizes 4.5m amphetamine pills hidden in oranges". 30 June 2021. https://www.aljazeera.com/news/2021/6/30/saudi-arabia-seizes-4-5m-amphetamine-pills-hidden-in-oranges. 
  66. ↑ "Saudis bust bid to smuggle 2 million Captagon pills". 24 July 2021. https://gulfnews.com/world/gulf/saudi/saudis-bust-bid-to-smuggle-2-million-captagon-pills-1.80876785. 
  67. ↑ "Zur chemischen Stabilität des Fenetyllins" (in de). Archiv der Pharmazie 320 (12): 1272–1275. December 1987. doi:10.1002/ardp.198700045. PMID 3439867. 
  68. ↑ Kohlstaedt E, Klingler KH, DE patent 1123329, issued 1962, assigned to Chemiewerk Homburg Zweignieder.
  69. ↑ 69.0 69.1 69.2 You, Z.-Y., Chen, Y.-J., Wang, Y.-Y., & Chen, C. (2008). Synthesis of Deuterium Labeled Standards of 1-Benzylpiperazine, Fenetylline, Nicocodeine and Nicomorphine. Journal of the Chinese Chemical Society, 55(3), 663–667. https://doi.org/10.1002/jccs.200800099
  70. ↑ Kikura, R., & Nakahara, Y. (1997). Hair analysis for drugs of abuse. XVI. Disposition of fenethylline and its metabolite into hair and discrimination between fenethylline use and amphetamine use by hair analysis. Journal of Analytical Toxicology, 21(4), 291–296. https://doi.org/10.1093/jat/21.4.291



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