What is Fenethylline, and what are its primary components?

Fenethylline, also spelled fenetylline or phenethylline, is a codrug of amphetamine and theophylline, meaning it is a single molecule that acts as a mutual prodrug for both of these active stimulants. A prodrug is a medication that is administered in an inactive or less active form and is then metabolized in the body into its active drug components.

What are some other names and historical brand names for Fenethylline?

Other names for Fenethylline include amphetaminoethyltheophylline and amfetyline. Historically, it was marketed as a psychostimulant under the brand names Captagon, Biocapton, and Fitton. The brand name 'Captagon' is now frequently used generically to refer to illicitly produced fenethylline.

What is the current legal status of Fenethylline in most countries?

Fenethylline is currently illegal in most countries and is primarily produced for illicit use.

What was the estimated global market value of illicit Fenethylline in 2023?

In 2023, the illicit global market for fenethylline was estimated to be worth approximately US$57 billion.

Which region is the main area for illicit Fenethylline use?

Abuse of fenethylline, often referred to by its former brand name Captagon, is common primarily in the Middle East.

What was Syria's role in the global supply and export of Captagon under the Assad regime?

Under the Assad regime, Syria was the world's largest producer of Captagon, responsible for about 80% of the global supply. Smuggling of Captagon became Syria's principal export, surpassing the total value of all other exports during the Syrian civil war from 2011 to 2024.

What impact did the fall of the Assad government in December 2024 have on Captagon trade in Syria?

Following the fall of the Assad government in Syria in December 2024, anti-Assad forces discovered warehouses filled with Captagon and manufacturing equipment. The new government destroyed the seized Captagon, and the trade reportedly decreased by approximately 90%.

For how long was Fenethylline used therapeutically, and what was its perceived advantage over amphetamine?

Fenethylline was used for approximately 25 years as a milder alternative to amphetamine and related compounds. A key advantage was that it did not increase blood pressure to the same extent as an equivalent dose of amphetamine, making it potentially suitable for patients with cardiovascular conditions.

What were the historical therapeutic uses of Fenethylline, despite lacking FDA approval?

Despite not having FDA-approved indications, Fenethylline was used in the treatment of 'hyperkinetic children,' a condition now known as attention deficit hyperactivity disorder (ADHD), and less commonly for narcolepsy and depression.

When and why was Fenethylline classified as a Schedule I controlled substance in the United States?

Fenethylline was listed as a Schedule I controlled substance in the United States in 1981. This classification was due to its chemical similarity to amphetamine, despite being considered to have fewer side effects and less potential for abuse at the time.

How is the Fenethylline molecule chemically structured?

The fenethylline molecule is formed when theophylline is covalently linked with amphetamine by an alkyl chain. A covalent bond is a chemical bond that involves the sharing of electron pairs between atoms.

How is Fenethylline metabolized in the body, and what are the active stimulant drugs it forms?

Fenethylline is metabolized by the body to form two active stimulant drugs: amphetamine, which accounts for 24.5% of an oral dose, and theophylline, which accounts for 13.7% of an oral dose. Metabolism is the set of chemical reactions that occur in living organisms to maintain life.

What is the nature of the physiological effects of Fenethylline?

The physiological effects of fenethylline appear to result from a synergistic effect between the amphetamine and theophylline produced following its metabolism. A synergistic effect occurs when the combined effect of two or more substances is greater than the sum of their individual effects.

Does Fenethylline have any direct pharmacological actions before being metabolized?

While its actions before cleavage are not entirely clear, fenethylline appears to act directly at several serotonin receptors. Serotonin receptors are a group of G protein-coupled receptors and ligand-gated ion channels found in the central and peripheral nervous systems.

What types of substances are often found in counterfeit 'Captagon' tablets?

Counterfeit 'Captagon' tablets often contain other amphetamine derivatives that are easier to produce, as well as a mix of amphetamines, caffeine, and various fillers. However, some analyzed counterfeit pills still contain actual fenethylline, indicating ongoing illicit production of the drug itself.

What was the estimated value of the Assad regime's annual fenethylline revenues in 2022, in comparison to the Mexican illicit drug market?

The Assad regime's annual fenethylline revenues were estimated to be worth US$57 billion in 2022, which was approximately three times the total trade of the entire Mexican illicit drug market.

What were the reported prices for Captagon pills in Lebanon in July 2019 and in Saudi Arabia in 2021?

In July 2019, Captagon pills were sold for $1.50 to $2.00 each in Lebanon. By 2021, low-quality pills were sold locally in Syria for less than $1, while high-quality pills smuggled abroad could cost upwards of $14 each in Saudi Arabia.

What percentage of young people in Saudi Arabia were reported to be addicted to fenethylline in 2017?

According to Abdelelah Mohammed Al-Sharif, secretary general of the National Committee for Narcotics Control, 40% of users between the ages of 12 and 22 in Saudi Arabia were addicted to fenethylline in 2017.

Describe the significant drug trafficking incident involving a Saudi royal family member in Beirut in October 2015.

In October 2015, Prince Abdel Mohsen Bin Walid Bin Abdulaziz, a member of the Saudi royal family, and four other individuals were detained in Beirut on drug trafficking charges. Airport security had discovered two tons of fenethylline pills and some cocaine on a private jet that was scheduled to depart for Riyadh, the capital of Saudi Arabia.

What large seizure of fenethylline was made by Turkish authorities in November 2015?

In November 2015, Turkish authorities seized two tonnes of fenethylline, amounting to about eleven million pills, during raids conducted in the Hatay region along the Syrian border. These pills had been produced in Syria and were being shipped to countries in the Arab states of the Persian Gulf.

What drug-related discoveries were made by the Lebanese Army in December 2015?

In December 2015, the Lebanese Army announced the discovery of two large-scale drug production workshops in the north of the country, where they seized significant quantities of fenethylline pills. Additionally, three tons of fenethylline and hashish were seized at Beirut Airport, having been concealed in school desks intended for export to Egypt.

What connection was found between Fenethylline and the 2016 Nice truck attack?

Traces of fenethylline were found on a mobile phone used by Mohamed Lahouaiej Bouhlel, the French-Tunisian individual responsible for the 2016 Nice truck attack, which killed eighty-four civilians on Bastille Day.

What notable seizure of fenethylline pills occurred at Charles de Gaulle Airport in May 2017?

In May 2017, French customs at Charles de Gaulle Airport seized 750,000 fenethylline pills that were being transported from Lebanon and destined for Saudi Arabia.

What did investigations reveal about the composition of seized 'Captagon' products in France in 2017?

Further investigations into 'Captagon' products seized in France in 2017 indicated that they primarily contained a mixture of amphetamine and theophylline, rather than pure fenethylline.

Describe a significant seizure of fenethylline pills at the Al-Haditha crossing in Saudi Arabia in January 2018.

In January 2018, Saudi Arabia seized 1.3 million fenethylline pills at the Al-Haditha crossing, which is located near the border with Jordan, during an anti-smuggling operation.

What illicit cargo was intercepted by Greek authorities from a Syrian ship in December 2018?

In December 2018, Greece intercepted a Syrian ship that was sailing towards Libya, carrying six tonnes of processed cannabis and three million fenethylline pills.

What record amount of amphetamine Captagon was seized in Greece in July 2019?

In July 2019, Greek authorities seized a record amount of amphetamine Captagon, totaling 33 million pills and weighing 5.25 tonnes, which had been shipped from Syria.

What quantity of fenethylline pills was discovered on a boat in the United Arab Emirates in July 2019?

In July 2019, authorities in the United Arab Emirates found 800,000 fenethylline pills on a boat.

How did Saudi customs at Al-Haditha prevent drug smuggling in August 2019?

In August 2019, Saudi customs at Al-Haditha successfully seized over 2.5 million fenethylline pills that were discovered hidden inside a truck and a private vehicle.

What large shipment of fenethylline pills was found in electric cables from Syria to Jebel Ali in February 2020?

In February 2020, the UAE discovered 35 million fenethylline pills concealed within a shipment of electric cables that originated from Syria and was destined for Jebel Ali.

What action did Saudi Arabia take in April 2020 following a large seizure of fenethylline pills smuggled from Syria?

In April 2020, after seizing 44.7 million fenethylline pills smuggled from Syria, Saudi Arabia imposed an import ban on fruits and vegetables from Lebanon, citing concerns about drug smuggling. This action caused the price of Lebanese lettuce to plummet.

Describe the large-scale anti-drug operation in Italy in July 2020 involving Captagon.

In July 2020, an anti-drug operation in Italy, coordinated by the Guardia di Finanza and Customs and Monopolies Agency, resulted in the seizure of fourteen tonnes of amphetamines, labeled as Captagon. These drugs, initially thought by Italian authorities to have been produced by ISIS, were found in three shipping containers filled with approximately 84 million pills in the southern port of Salerno.

What significant fenethylline seizures were made by Egyptian authorities in November 2020?

In November 2020, Egyptian authorities seized two shipments of fenethylline pills at Damietta port that originated from Syria. The first shipment contained over 3.2 million tablets, while the second contained 11 million tablets.

What was the estimated value of the 14 tonnes of fenethylline seized by Italian authorities in December 2020?

In December 2020, Italian authorities seized approximately 14 tonnes of fenethylline, consisting of about 85 million pills, which had arrived from Latakia, Syria, and was destined for Libya. This seizure was estimated to be worth around $1 billion.

What large drug haul from Lebanon was intercepted by Egyptian authorities at Port Said in January 2021?

In January 2021, Egyptian authorities at Port Said intercepted a shipment that had arrived from Lebanon, seizing eight tons of fenethylline and an additional eight tons of hashish.

How were 5 million fenethylline pills concealed in a shipment seized at Beirut port in February 2021?

In February 2021, Lebanese customs at Beirut port seized a shipment of 5 million fenethylline pills that were hidden inside a tile-making machine. These pills were intended for Greece and Saudi Arabia.

What method of concealment was used for 5.3 million fenethylline pills seized by Saudi authorities in April 2021?

In April 2021, Saudi authorities discovered 5.3 million fenethylline pills that had been hidden within fruits imported from Lebanon.

The source material includes an image depicting 127 bags of fenethylline seized in Syria before being destroyed in May 2018. What does this image illustrate?

The image illustrates a significant seizure of fenethylline, specifically 127 bags, that took place in Syria in May 2018, prior to the destruction of the illicit drug.

What role did fenethylline play in the Syrian civil war?

Fenethylline played a significant role in the Syrian civil war, as its production and sale generated large revenues that were likely used to fund the purchase of weapons, and the drug itself was used as a stimulant by combatants.

What factors contributed to the industrialization and increased production of fenethylline in Syria?

Poverty and international sanctions that limited legal exports were contributing factors to the increased production of fenethylline in Syria. This led to increased industrialization, adaptation, and technical sophistication in its manufacture.

How did *The Guardian* characterize the impact of fenethylline production on Syria's economy in May 2021?

In May 2021, *The Guardian* described the effects of fenethylline production on Syria's economy as 'a dirty business that is creating a near-narco-state,' highlighting Syria's position as the global center of fenethylline production.

What was found hidden in a shipment of iron plates from Lebanon to Jeddah port in June 2021?

In June 2021, Saudi authorities at Jeddah port seized 14 million fenethylline tablets that were hidden inside a shipment of iron plates originating from Lebanon.

Which elite division of the Syrian Army was reported to oversee fenethylline production and distribution?

The Syrian Army's elite 4th Armoured Division, commanded by Maher al-Assad, the brother of Syrian President Bashar al-Assad, was reported to oversee much of the production and distribution of fenethylline, along with other drugs like crystal meth. This unit controlled manufacturing facilities, packing plants, and smuggling networks across Syria.

What nickname is sometimes given to fenethylline due to its use by jihadist fighters?

Fenethylline is sometimes dubbed the 'jihad drug' because it is used by some jihadist fighters as a major stimulant.

What are the reported effects of fenethylline on users, particularly combatants, according to the source?

Fenethylline quickly produces a euphoric intensity, enabling users to stay awake for extended periods, remain calm and focused, and helps to suppress feelings of fear and hunger during prolonged operations. It can also induce a sense of invincibility.

What extreme behavioral effects were described by an illegal Syrian manufacturer regarding high doses of fenethylline?

An illegal Syrian manufacturer stated that if someone takes a large number of pills, such as 30 or more, they can become violent, crazy, paranoid, and unafraid of anything. They develop a strong urge for fighting and killing, shooting at whatever they see, and losing all feeling or empathy for others.

What dangerous side effects of fenethylline have doctors reported?

Doctors have reported that fenethylline has dangerous side effects, including psychosis and brain damage. Psychosis is a severe mental disorder in which thought and emotions are so impaired that contact is lost with external reality.

How did a former fighter associated with the Muslim Brotherhood describe the effect of high doses of fenethylline on combatants?

A former fighter associated with the Muslim Brotherhood described that combatants taking high doses of fenethylline 'go blank,' experience spiking heart rates, and lose all connection to their emotions and thoughts, sometimes resulting in a 'zombie-like detachment.'

What was the alleged connection between fenethylline use and the jihadist group ISIS?

Fenethylline use was associated with the rise of the jihadist group ISIS. A 19-year-old fighter named Kareem, who claimed to have fought with ISIS, told CNN in 2014 that they were given 'hallucinogenic pills that would make you go to battle not caring if you live or die.'

Fenethylline Wiki: Fenethylline Unveiled: The Complex Legacy of a Potent Stimulant

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Overview

A Unique Codrug

Fenethylline, also known by its International Nonproprietary Name (INN) fenetylline, is a fascinating pharmaceutical compound classified as a codrug. It is essentially a molecular fusion of two active stimulants: amphetamine and theophylline. This unique structure means it functions as a mutual prodrug, delivering both components upon metabolism within the body.

Naming & Branding

Beyond its chemical designation, Fenethylline has been known by several other names, including phenethylline, amphetaminoethyltheophylline, and amfetyline. Historically, it was marketed under brand names such as Captagon, Biocapton, and Fitton. Today, the brand name "Captagon" has become a generic term, frequently used to refer to illicitly produced fenethylline, highlighting its pervasive presence in the black market.

Legal Status

Despite its initial medical applications, Fenethylline is now illegal in the vast majority of countries worldwide. Its classification as a Schedule I controlled substance in the United States in 1981, followed by its listing by the World Health Organization for international scheduling under the Convention on Psychotropic Substances in 1986, solidified its global prohibition. This legal shift underscores the significant concerns regarding its potential for abuse and its societal impact.

History

Origins and Early Use

Fenethylline was first synthesized in 1961 by the German pharmaceutical company Degussa AG. For approximately 25 years, it was utilized as a therapeutic agent, offering a perceived milder alternative to traditional amphetamine and its related compounds. This initial period saw its application in various medical contexts, reflecting a different understanding of stimulant pharmacology at the time.

Therapeutic Applications

While never receiving FDA approval in the United States, Fenethylline found use in treating "hyperkinetic children," a condition now recognized as Attention Deficit Hyperactivity Disorder (ADHD). Less commonly, it was also prescribed for narcolepsy and certain forms of depression. A notable advantage cited for Fenethylline was its reduced impact on blood pressure compared to equivalent doses of amphetamine, making it a potentially safer option for patients with pre-existing cardiovascular conditions.

Global Prohibition

Despite its perceived benefits and lower abuse potential compared to amphetamine, the chemical similarity between the two compounds ultimately led to Fenethylline's reclassification. In 1981, it was designated a Schedule I controlled substance in the United States. This was followed by a global consensus in 1986, when the World Health Organization recommended its international scheduling under the Convention on Psychotropic Substances, effectively rendering it illegal in most nations and marking the end of its legitimate medical use.

Chemistry

Molecular Architecture

The Fenethylline molecule is a sophisticated construct where theophylline, a xanthine derivative, is covalently bonded to amphetamine via an alkyl chain. This structural linkage is key to its function as a prodrug, allowing the combined entity to be absorbed and then broken down into its active components within the body.

Metabolic Transformation

Upon oral administration, Fenethylline undergoes metabolism, yielding its two primary active constituents: amphetamine and theophylline. Studies indicate that approximately 24.5% of an oral dose is metabolized into amphetamine, while 13.7% converts to theophylline. The physiological effects observed in users are believed to stem from a complex interplay and synergistic action between these two potent stimulants.

Receptor Interactions

While the precise pharmacological actions of the intact Fenethylline molecule, prior to its metabolic cleavage, are not fully elucidated, research suggests it may exert direct effects on several serotonin receptors. This indicates a more nuanced mechanism of action than simply being a delivery vehicle for amphetamine and theophylline, potentially contributing to its overall psychoactive profile.

Illicit Trade

A Global Phenomenon

The abuse of Fenethylline, predominantly under its former brand name Captagon, is particularly widespread in the Middle East. Despite its global illegality, counterfeit versions of the drug are readily available, often indistinguishable from genuine pills to the untrained eye. The illicit global market for Fenethylline was estimated to be a staggering US$57 billion in 2023, underscoring its significant economic footprint in the shadow economy.

The Counterfeit Landscape

Many illicit "Captagon" tablets circulating contain a variety of substances, including other amphetamine derivatives that are simpler and cheaper to produce, along with caffeine and various fillers. These are often pressed and stamped to mimic the appearance of authentic Captagon pills. However, forensic analyses confirm that some counterfeit pills do indeed contain Fenethylline, indicating ongoing clandestine production of the original compound.

Syria's Narco-State Status

For over a decade, under the Assad regime (2011-2024), Syria emerged as the world's largest producer of Fenethylline, accounting for approximately 80% of the global supply. The production and export of this drug became the country's principal export, generating over 90% of its foreign currency revenue and earning it the moniker of a "narco-state." Following the fall of the Assad government in December 2024, reports indicate a significant decline in the Captagon trade, with former rebels seizing and destroying vast quantities of the drug and manufacturing equipment.

The scale of illicit Fenethylline trafficking is evidenced by numerous large-scale seizures:

2015: Saudi prince detained in Beirut with two tons; Turkey seizes 11 million pills (2 tons) from Syria; Lebanese Army busts two factories and seizes three tons.
2016: Traces found on Nice truck attacker.
2017: French customs at Charles de Gaulle Airport seize 750,000 pills (135 kg) from Lebanon, and two other consignments.
2018: Saudi Arabia seizes 1.3 million pills at Al-Haditha crossing; Greece intercepts Syrian ship with three million pills.
2019: Greece seizes 33 million pills (5.25 tonnes) from Syria; UAE finds 800,000 pills; Saudi customs seize over 2.5 million pills.
2020: UAE finds 35 million pills in electric cables from Syria; Saudi Arabia seizes 44.7 million pills from Syria, leading to an import ban on Lebanese produce; Italy seizes 14 tonnes (84 million pills) from Syria; Egypt seizes 3.2 million and 11 million tablets from Syria; Italian authorities seize 14 tonnes (85 million pills) from Latakia, Syria, valued at $1 billion.
2021: Egyptian authorities seize eight tons of Fenethylline from Lebanon; Lebanon seizes five million pills hidden in a tile-making machine; Saudi authorities discover 5.3 million pills hidden in fruits from Lebanon, 14 million in iron plates, 4.5 million in orange cartons, and 2.1 million in tomato paste.

Conflict Use

The "Jihad Drug"

Fenethylline has gained notoriety as the "jihad drug," allegedly used by certain Islamist militants and terrorists in conflict zones, particularly during the Syrian civil war. Its stimulant properties are believed to induce a state of euphoric intensity, enabling users to remain awake for extended periods, maintain focus, and suppress feelings of fear and hunger during prolonged operations.

Altered Perception

Psychiatrists describe the drug's effects as imparting a "sense of well-being and euphoria," coupled with a dangerous belief in one's "invincibility." Former fighters have reported experiencing a "blank" state, spiking heart rates, and a profound detachment from emotions and thoughts, sometimes described as a "zombie-like" effect. High doses are said to lead to extreme violence, paranoia, and a complete lack of empathy, allowing individuals to engage in brutal acts without remorse.

Health Ramifications

Beyond its psychological effects, Fenethylline use carries severe health risks, including psychosis and potential brain damage. Many combatants, unaware of the substance they were consuming, reportedly developed addictions. Claims of Fenethylline use by Hamas fighters during the October 7 attacks have been made by Israeli officials, though experts have expressed skepticism regarding the reported forms (liquid and powder) of the drug found, suggesting the possibility of other stimulants or factors like sleep deprivation.

Synthesis

Simplicity and Cost-Effectiveness

The clandestine chemical synthesis of Fenethylline is remarkably straightforward and inexpensive, a factor contributing significantly to its widespread illicit production. This ease of manufacture allows for large-scale operations in illicit laboratories, particularly in regions like the Middle East, where it has become a major source of illicit revenue.

Two-Step Laboratory Process

The synthesis of Fenethylline can be achieved in two primary laboratory steps, each requiring careful extraction and purification:

Alkylation of Theophylline: Theophylline (1) is subjected to an alkylation reaction using 1-bromo-2-chloroethane (2). This reaction yields 7-(β-chloroethyl)theophylline (3), also known as Benaphyllin or Eupnophile. This step involves a substitution reaction where the bromo-chloroethane attaches to the theophylline molecule.
Amine Displacement with Amphetamine: In the second step, the primary amine group present in amphetamine (4) acts as a nucleophile, displacing the terminal halide (chlorine) from the 7-(β-chloroethyl)theophylline (3). This displacement reaction forms the final Fenethylline molecule (5).

This process can be adapted using analogous reagents and solvents. For instance, employing tetradeutero-vic-dichloroethane instead of 1-bromo-2-chloroethane can produce a perdeuterated-bridge analogue of Fenethylline, useful for research and analytical purposes.

Detection

Analytical Methods

To identify Fenethylline and its related metabolites in biological samples, advanced analytical techniques are employed. A prominent method is Gas Chromatography-Mass Spectrometry (GC-MS). This technique allows for the precise separation and identification of Fenethylline and its breakdown products, such as amphetamine and theophylline, in various matrices like plasma, urine, and hair.

Hair Analysis

Hair testing has proven to be a particularly valuable tool for determining a history of Fenethylline use. Unlike blood or urine tests, which typically detect recent drug exposure, hair analysis can reveal drug use over a longer period due to the incorporation of substances into the growing hair shaft. Furthermore, hair analysis can aid in discriminating between direct Fenethylline use and the use of its precursor, amphetamine, by identifying specific metabolic markers.

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References

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Fenethylline Unveiled

💡 Dive in with Flashcard Learning! 💡

Overview ℹ️

💊 A Unique Codrug

🏷️ Naming & Branding

⚖️ Legal Status

History 📜

🔬 Origins and Early Use

🧠 Therapeutic Applications

🚫 Global Prohibition

Chemistry ⚛️

🔗 Molecular Architecture

🔄 Metabolic Transformation

🧠 Receptor Interactions

Illicit Trade 💸

🌐 A Global Phenomenon

🎭 The Counterfeit Landscape

🇸🇾 Syria's Narco-State Status

Conflict Use ⚔️

🛡️ The "Jihad Drug"

🎭 Altered Perception

⚠️ Health Ramifications

Synthesis 🧪

💰 Simplicity and Cost-Effectiveness

⚙️ Two-Step Laboratory Process

Detection 🔍

🧪 Analytical Methods

💇‍♀️ Hair Analysis

Teacher's Corner 🧑‍🏫

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References

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Disclaimer ⚠️

📜 Important Notice

Dive in with Flashcard Learning!

Overview

A Unique Codrug

Naming & Branding

Legal Status

History

Origins and Early Use

Therapeutic Applications

Global Prohibition

Chemistry

Molecular Architecture

Metabolic Transformation

Receptor Interactions

Illicit Trade

A Global Phenomenon

The Counterfeit Landscape

Syria's Narco-State Status

Conflict Use

The "Jihad Drug"

Altered Perception

Health Ramifications

Synthesis

Simplicity and Cost-Effectiveness

Two-Step Laboratory Process

Detection

Analytical Methods

Hair Analysis

Teacher's Corner

True or False?

Test Your Knowledge!

Gamer's Corner

Discover other topics to study!

References

Feedback & Support

Disclaimer

Important Notice