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AHFS/Drugs.com | International Drug Names |
Routes of administration | Oral |
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ECHA InfoCard | 100.115.827 |
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Formula | C18H23N5O2 |
Molar mass | 341.415 g·mol−1 |
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Chirality | Racemic 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
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. [6] 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. [7]
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. [7] [ circular reference ]
The fenethylline molecule results when theophylline is covalently linked with amphetamine by an alkyl chain. [8]
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, [9] [10] [11] although how is not entirely clear, and seems to involve a synergistic effect between amphetamine and theophylline produced following metabolism. [7] [12] The pharmacological actions of fenethylline before cleavage also remain poorly established, though it appears to act directly at several serotonin receptors. [13]
Abuse of fenethylline of the brand name Captagon is common in the Middle East, [14] [15] and counterfeit versions of the drug continue to be available despite its illegality. [16] [17] 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. [18] The Assad regime's annual Captagon merchandise is estimated to have been worth US$57 billion in 2022, about three times the total trade of all Mexican drug barons. [19] [20] [4]
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. [21] 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. [22] 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. [23] 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. [24] 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. [14]
According to some leaks, militant groups export the drug in exchange for weapons and cash. [25] [26] 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. In 2017, Captagon was the most popular recreational drug in the Arabian Peninsula. [27]
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. [28] [29] [30] 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. [31]
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. [32]
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. [33]
In May 2017, French customs at Charles de Gaulle Airport seized 750,000 Captagon pills being transported from Lebanon to Saudi Arabia. [34] 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. [35] Further investigation showed that the seized products mainly contained a mixture of amphetamine and theophylline. [36]
In January 2018, Saudi Arabia seized 1.3 million Captagon pills at the Al-Haditha crossing near the border with Jordan. [37] In December 2018, Greece intercepted a Syrian ship sailing for Libya, carrying six tonnes of processed cannabis and three million Captagon pills. [38] In July 2019, a shipment of thirty-three million Captagon pills, weighing 5.25 tonnes, was seized in Greece coming from Syria. [39] In July 2019, eight hundred thousand Captagon pills were found on a boat in the United Arab Emirates. [40] In August 2019, Saudi customs at Al-Haditha seized 2,579,000 Captagon pills found inside a truck and a private vehicle. [41]
In February 2020, the UAE found thirty-five million Captagon pills in a shipment of electric cables from Syria to Jebel Ali. [42] In April 2020, Saudi Arabia seized 44.7 million Captagon pills smuggled from Syria, [43] and citing drug smuggling concerns, imposed an import ban on fruits and vegetables from Lebanon, causing the price of Lebanese lettuce to plummet. [44] [45] 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, [46] [47] [48] which were found in three shipping containers filled with around 84 million pills, in the southern port of Salerno. [46] [47] [48] [49]
In November 2020, Egypt seized two shipments of Captagon pills at Damietta port coming from Syria. The first had 3,251,500 tablets, [50] while the second contained 11 million tablets. [51] 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. [52]
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. [53] 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. [54] In April 2021, Saudi authorities discovered 5.3 million Captagon pills hidden in fruits imported from Lebanon. [55]
The drug is playing a role in the Syrian civil war. [56] [57] 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. [57] [58] [59] Poverty and international sanctions that limit legal exports are contributing factors. [60]
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. [61] In June 2021, Saudi authorities at Jeddah port seized fourteen million Captagon tablets hidden inside a shipment of iron plates coming from Lebanon. [62] In the same month, Saudi authorities seized a shipment of 4.5 million Captagon pills, smuggled inside several orange cartons, at Jeddah port. [63] In July 2021, Saudi customs discovered 2.1 million Captagon pills at Al-Haditha hidden in a tomato paste shipment. [64]
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. [14] 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." [14]
Faith and political agenda are not the only motivations of Jihadists. Just below it, experts suspect, they're powered by something else: captagon. Called the jihad drug, captagon has for years been a staple among jihad fighters. The drug is tailor-made for the battlefield because of its ability to give soldiers superhuman energy and courage. It quickly produces a euphoric intensity in users, allowing fighters to stay up for days. They remain calm and focused. Their senses become very sharp. It helps to eliminate fear and hunger, which is very important in conducting a long fight. [24] [65] [66] Boosting their fervor and resistance to fatigue and hunger, captagon is transforming fighters into killing machines. [67] The drug makes them go to battle not caring if they live or die. It causes a surge of energy and a euphoric high giving sense that they are invincible and that nothing can harm them. [68] [65] Those who go on jihad missions take a lot of it to prepare, says a former fighter associated with the Muslim Brotherhood. He described the effect: "They go blank. Their heart rate spikes. They lose all connection to their emotions and thoughts." Some commented on this effect as a "zombielike detachment." [69] [70] They will have a thirst for fighting and killing and will shoot at whatever they see. [71]
Captagon allows fighters to withstand such pain as being shot by bullets. [68] A drug control officer in the central city of Homs told Reuters had observed the effects of captagon on protesters and fighters held for questioning. If beaten, they would not feel much pain and some of them would even laugh. The interrogators would leave the prisoners for about two days without questioning them while the effects of captagon wore off, and then interrogation would become easier. [24] Doctors report that the drug has dangerous side effects, including psychosis and brain damage. [24] But knowing they are going to die, the Jihadists care little whatever harm or side effects the drugs have. [68]
Captagon fueled the rise of ISIS. [65] [68] One 19-year-old fighter named Kareem, who said he fought alongside ISIS for more than a year, told CNN in 2014: “They gave us drugs, hallucinogenic pills that would make you go to battle not caring if you live or die.” [68]
In February 2023, Israel’s Ministry of Defense thwarted an attempt to smuggle thousands of captagon tablets into the Gaza Strip. [72] Hamas claimed on the occasion that it seized 50,000 captagon pills on the border and blamed Israel for attempt to dope Gaza. [73] Later that year, captagon-like substance was found on at least some Hamas members killed during or after October 7. In the pockets of their clothes and tactical gear along with bullets were found bags with hundreds of pills of captagon. Small bottles of liquid containing a white fluid with traces of captagon also were found on the bodies of the attackers. [74] [75] Videos compiled by the Israeli government of the Hamas attack — cobbled together from cell phones, GoPros, and car and surveillance cameras — definitely leave the impression that at least some of the militants were under the influence of the drug. The length and ferocity of the assault on October 7 also suggests that at least some of the militants were chemically enhanced. [76] [77] Captagon was used by the ISIS attackers in the Crocus City Hall attack in 2024. [78] [79]
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). [82]
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). [82]
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. [83]
The illegal drug trade, drug trafficking, or narcotrafficking is a global black market dedicated to the cultivation, manufacture, distribution and sale of prohibited drugs. Most jurisdictions prohibit trade, except under license, of many types of drugs through the use of drug prohibition laws. The think tank Global Financial Integrity's Transnational Crime and the Developing World report estimates the size of the global illicit drug market between US$426 and US$652 billion in 2014 alone. With a world GDP of US$78 trillion in the same year, the illegal drug trade may be estimated as nearly 1% of total global trade. Consumption of illegal drugs is widespread globally, and it remains very difficult for local authorities to reduce the rates of drug consumption.
Narco-state is a political and economic term applied to countries where all legitimate institutions become penetrated by the power and wealth of the illegal drug trade. The term was first used to describe Bolivia following the 1980 coup of Luis García Meza which was seen to be primarily financed with the help of narcotics traffickers. Other well-known examples are Honduras, Guinea-Bissau, Mexico, Myanmar and Syria, where drug cartels produce, ship and sell drugs such as captagon, cocaine, heroin and marijuana.
Rifaat Ali al-Assad is the younger brother of the late President of Syria, Hafez al-Assad, and Jamil al-Assad, and the uncle of the incumbent President Bashar al-Assad. He was the commanding officer of the ground operations of the 1982 Hama massacre ordered by Hafez al-Assad.
Maher al-Assad is a Syrian general and commander of the Syrian Army's elite 4th Armoured Division, which together with Syria's Military Intelligence form the core of the country's security forces. He is also a member of the Central Committee of the Ba'ath Party's Syrian Regional Branch.
The Syrian civil war is an ongoing multi-sided conflict in Syria involving various state-sponsored and non-state actors. In March 2011, popular discontent with the rule of Bashar al-Assad triggered large-scale protests and pro-democracy rallies across Syria, as part of the wider Arab Spring protests in the region. After months of crackdown by the government's security apparatus, various armed rebel groups such as the Free Syrian Army began forming across the country, marking the beginning of the Syrian insurgency. By mid-2012, the crisis had escalated into a full-blown civil war.
This page provides maps and a list of cities and towns during the Syrian civil war.
The Axis of Resistance is an informal Iranian-led political and military coalition in West Asia and North Africa. It most notably includes the Syrian government, the Lebanese political party and militant group Hezbollah, the Yemeni political and military organization Ansar Allah, and a variety of Palestinian militant groups.
Foreign involvement in the Syrian civil war refers to political, military and operational support to parties involved in the ongoing conflict in Syria that began in March 2011, as well as active foreign involvement. Most parties involved in the war in Syria receive various types of support from foreign countries and entities based outside Syria. The ongoing conflict in Syria is widely described as a series of overlapping proxy wars between the regional and world powers, primarily between the United States and Russia as well as between Iran and Saudi Arabia.
The following is a timeline of the Syrian Civil War from August to December 2015. Information about aggregated casualty counts is found at Casualties of the Syrian Civil War.
Saudi Arabia's involvement in the Syrian Civil War involved the large-scale supply of weapons and ammunition to various rebel groups in Syria during the Syrian Civil War.
Very Big Shot is a 2015 Lebanese black comedy film directed by Mir-Jean Bou Chaaya. It was screened in the Discovery section of the 2015 Toronto International Film Festival. The original soundtrack was composed, arranged and produced by Michel Elefteriades. It was selected as the Lebanese entry for the Best Foreign Language Film at the 89th Academy Awards but it was not nominated.
Collaboration with the Islamic State refers to the cooperation and assistance given by governments, non-state actors, and private individuals to the Islamic State (IS) during the Syrian Civil War, Iraqi Civil War, and Libyan Civil War.
Timber Sycamore was a classified weapons supply and training program run by the United States Central Intelligence Agency (CIA) and supported by some Arab intelligence services, including Saudi intelligence. The aim of the programme was to remove Syrian president Bashar al-Assad from power. Launched in 2012 or 2013, it supplied money, weaponry and training to Syrian opposition militias fighting al-Assad's forces in the Syrian civil war. According to US officials, the program was run by the CIA's Special Activities Division and has trained thousands of rebels. President Barack Obama secretly authorized the CIA to begin arming Syria's embattled rebels in 2013. The program became public knowledge in mid-2016.
The diplomatic relations between Lebanon and Saudi Arabia are the relationship between two Arab nations in the Middle East. Lebanon has an embassy in Riyadh and Saudi Arabia has an embassy in Beirut.
Corruption in Syria follows the familiar patterns of state-based corruption, namely government officials abusing their political powers for private gain in the country of Syria.
Syrian foreign policy during the presidency of Bashar al-Assad is based on continuity from the Cold War-era policies of his father and predecessor, Hafiz al-Assad. Hafiz al-Assad was a strong supporter of Soviet Union and aligned Ba'athist Syria closely with the Eastern Bloc. During this period, Syria adopted a strong anti-Zionist posture in the region, based on its military doctrine of gaining "strategic parity" and forming joint Arab initiatives.
The drug economy in Lebanon refers to the expanding Lebanese involvement in both drug production and trade, a phenomenon substantiated by studies. The economic and political upheaval in Lebanon, as delineated in a study by the Euro-Gulf Information Center, has driven Hezbollah, wherein narcotics serve as a notable revenue stream, to intensify its involvement in the drug economy. Western intelligence agencies estimate that Lebanon produces over 4 million pounds of hashish and 20,000 pounds of heroin annually, generating profits exceeding US$4 billion. According to The Washington Post, Lebanon's drug industry contributes substantially to the country's economy, accounting for over half of its foreign-exchange earnings.
This is an overview of crime in Jordan.
The Syrian Captagon industry is responsible for about 80% of the global production of the Captagon drug. Syria exports the drug to various countries, mainly in the Middle East region, including Jordan, Iraq, Saudi Arabia, Gulf states, and Egypt, as well as to organizations such as Hamas and ISIS. The drug export is one of the main sources of income for the government of Bashar al-Assad, helping it to rebuild the country from the economic crisis that hit it following the civil war that took place in the country.
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.