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Structural formula
Structural formula of fentanyl
Non-proprietary name Fentanyl
other names
  • N - (1-Phenethyl-4-piperidyl) propionanilide ( IUPAC )
  • Fentanylum ( Latin )
  • Fentanyli citras ( Latin , as citrate)
Molecular formula C 22 H 28 N 2 O
Brief description

White to almost white, polymorphic powder

External identifiers / databases
CAS number
  • 437-38-7
  • 990-73-8 (citrate salt)
PubChem 3345
DrugBank DB00813
Wikidata Q407541
Drug information
ATC code

N02 AB03 N01 AH01

Drug class

Opioid - analgesic

Molar mass 336.47 g · mol -1
Melting point
safety instructions
Please note the exemption from the labeling requirement for drugs, medical devices, cosmetics, food and animal feed
GHS labeling of hazardous substances
06 - Toxic or very toxic 08 - Dangerous to health


H and P phrases H: 300-310-317-330-334
P: 260-264-280-284-302 + 350-310
Toxicological data
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Fentanyl is a synthetic opioid that is used as a pain reliever in anesthesia (during anesthesia) and for the treatment of acute and chronic pain that can only be adequately treated with opioid analgesics. Fentanyl acts as an agonist on the μ- opioid receptor . Fentanyl falls under the German and Swiss Narcotics Act as well as the Austrian Narcotics Act .


In 1960, Paul Janssen developed Fentanyl as the first anilinopiperidine (4-anilinopiperidine-4-carboxamide). Since then, a number of more controllable derivatives have been developed from fentanyl by modifying the molecular structure.


Fentanyl is commonly used as fentanyl dihydrogen citrate. There are four forms of application:

  • as intravenous administration (e.g. in anesthesia or emergency medicine )
  • as a transdermal therapeutic system (i.e. as a membrane plaster stuck to the skin , which then releases the active ingredient (at either 12.5, 25, 37.5, 50, 75 or 100 micrograms per hour) in a controlled manner for absorption through the skin; e.g. . Durogesic SMAT , generics )
  • as a fast-releasing formulation such as the oral-transmucosal therapeutic system ( Actiq from Elan Pharma ), which is used for breakthrough pain as a lozenge containing 200 to 1600 µg active ingredient with an integrated applicator on the oral mucosa, as a buccal tablet (trade name Effentora ) with 100 to 800 µg active ingredient or as a sublingual tablet (trade name Abstral ) with 50 to 800 µg fentanyl.
  • the fentanyl nasal spray ( PecFent from Archimedes Pharma or Instanyl from Takeda )

These rapid-release formulations are indicated for the treatment of breakthrough pain (very intense, minute-long pain, typical of advanced cancer) in adults who are already receiving basic opioid therapy for their tumor pain.


Fentanyl has a strong pain-relieving ( analgesic ) and sedating effect , as well as respiratory depressive , antitussive , pulse-slowing, blood pressure lowering, constipating and euphoric. It is about 70 to 100 or 120 times as potent as morphine (measured by mass, only a hundred twentieth the amount of fentanyl is necessary to achieve the same effect), has a higher effectiveness (the maximum effect is higher), while its duration of action is usually significantly shorter. Fentanyl works after five to twenty seconds when given intravenously . The maximum effect occurs after four to five minutes. The half-life is three to twelve hours. The effective dose ( ED 50 ) for treatment is 0.002 to 0.02 mg / kg body weight with constant breathing monitoring.

The analgesic duration of action of fentanyl depends on the drug form used: 48 to 72 hours for a transdermal patch, for transmucosal application 0.5 to 2 hours, for buccal tablets and sublingual tablets 4 to 6 hours.

Fentanyl is lipophilic , i. H. easily soluble in fat and therefore spreads quickly in fatty tissue. Fentanyl is mainly metabolized in the liver and less than ten percent of the time it is excreted unchanged by the kidneys .

The main area of ​​application of the intravenous form is the administration as pain reliever during operations in connection with a sleeping aid and optionally a muscle relaxant ( muscle relaxant ). Depending on the choice of sleeping aid, one speaks of “balanced anesthesia” or “total intravenous anesthesia” ( TIVA ). Because of the risk of respiratory depression, constant monitoring and the availability of a ventilation option is necessary. Due to its lipophilicity , fentanyl is sometimes stored and released again in adipose tissue, which is difficult to control. That is why the related substances alfentanil , remifentanil and sufentanil are often used today instead of fentanyl .

In the case of fentanyl-containing active substance patches, continuous monitoring of the vital functions is not necessary after a setting phase due to the uniform effect and the usually significantly lower dose compared to anesthesia.


The sedative effects of fentanyl can be increased by sedatives and alcohol. Serious circulatory and respiratory disorders can occur in connection with monoamine oxidase inhibitors . There should be at least 14 days between the use of MAOIs and fentanyl. Due to the plasma protein binding of 90%, there may be interactions with preparations such as furosemide , glibenclamide or omeprazole when used in pain plasters . The pathway of fentanyl via the cytochrome oxidase 450 , so that with simultaneous administration of CYP 3A4 - inducers (eg. St. John's wort preparations; accelerate the degradation of fentanyl) or CYP 3A4 inhibitors (eg. Ketoconazole , erythromycin , nefazodone , Diltiazem , grapefruit juice ; slow down the breakdown of fentanyl and can lead to increased plasma levels ) Interactions may occur.

Calcium antagonists: The combination of fentanyl (and other opioids) with calcium antagonists can lead to a potentiation of the analgesic effect in addition to reducing the development of tolerance. In 1985 the potentiating effect of nimodipine compared to the analgesic effect of fentanyl was described. The combined administration of 0.1 mg fentanyl together with nimodipine (1 µg / kg / min infusion) is said to have the same effectiveness as 2.45 mg fentanyl, which corresponds to a potentiation of 24.5 times. Further human experiments showed that, unlike nimodipine , nifedipine did not potentiate the fentanyl effect, but the effect of nimodipine in this study was also significantly weaker (3-fold potentiation) than in the first study.

The simultaneous administration of fentanyl-containing drugs with serotonergic drugs (SSRI / SNRI) poses a risk of developing a dangerous serotonin syndrome with symptoms such as agitation , coma , hallucinations , blood pressure crises , neuromuscular changes and palpitations , as was warned in March 2013.

Side effects

Like other opioids, fentanyl overdoses provokes a disorder of the central nervous system with impaired consciousness, somnolence and respiratory depression . The acute picture essentially shows pronounced sedation , miosis (constriction of the pupil) and respiratory depression, with this up to and including respiratory arrest. Fentanyl can be antagonized with naloxone .

Since 2005, the FDA has repeatedly reported serious side effects and deaths associated with fentanyl-containing transdermal therapeutic systems , 397 deaths in 2009 alone. In 2012, the Drugs Commission of the German Medical Association (AkdÄ) also pointed out that the indication for transdermal, fentanyl-containing patches must be strict. They should only be prescribed for chronic pain that can only be adequately alleviated with opioids and requires constant, continuous treatment. While the FDA only allows its use in patients who have taken 60 mg morphine per day or more for at least a week (or another opioid, respectively), the German specialist information advises that patients who have not previously taken opioids should initially give low-dose, non-delayed opioids. until the dose of the dose of 12.5 μg / h fentanyl (= 45 mg morphine / day ). and only then switch to a plaster.

In 2014, a Rote-Hand-Brief warned against "accidental transfer of the fentanyl patch to the skin of another person (e.g. while sharing a bed or during closer physical contact)". "To protect against accidental ingestion by children, the application site should be carefully selected and regularly monitored to ensure that the patch is still there."


For the reliable qualitative and quantitative determination of fentanyl in blood / blood plasma samples and urine , the coupling of gas chromatography or HPLC with mass spectrometry is used after appropriate sample preparation . These procedures are also used for forensic examinations. For doping control , these methods are also used. Also immunoassays used.

Substance Abuse, Overdose, and Potential Hazards

Since 2006 at the latest, the abuse of fentanyl has been increasing in the USA. In a report, the CDC spoke of 1,000 deaths between 2005 and 2007; most of the cases were recorded in Chicago , Philadelphia, and Detroit . In 2014 there were 4,200 dead. Preliminary data shows that fentanyl was responsible for a large proportion of the estimated 59,000 to 65,000 drug deaths in the US in 2016 (see opioid epidemic in the US ). In the district of Montgomery County drug deaths fentanyl or an analog was detected in January and February 2017 99 of the 100th According to the New York Times , at least 220 people died from fentanyl abuse in 2016 in Long Island alone .

One reason for the high death rate with fentanyl applications is the extremely high efficacy or narrow therapeutic range . While a therapeutic dose above 0.02 mg / kg body weight is only possible when using the heart-lung machine , the lethal dose for (rhesus) monkeys is already 0.03 mg / kg body weight. Fentanyl can be fatal in an amount as low as 2 mg for an adult of normal weight.

Fentanyl in powder form also poses a particular risk, as it is acquired as a pure substance before processing into finished medicinal products, but is also traded on the black market in order to then e.g. B. to be taken as an injection, or by nasal consumption. There are known incidents in which the powder was involuntarily swirled in the air - for example when a container with the substance was dropped. Fentanyl aerosol can unintentionally get into the nasal and / or oral mucosa. Unintentional absorption through the skin is also possible here.

Fentanyl is also used to stretch heroin. If the fentanyl is not evenly distributed, each dose contains different amounts of fentanyl and there can be deadly fentanyl hot spots in the stretched drug mass. Fentanyl, which is used in this way or sold directly on the black market, comes partly from legal pharmaceutical and partly from illegal production.

By introducing various chemical structural elements into the fentanyl molecule , a number of designer drugs have been synthesized, such as methylfentanyl and benzylfentanyl.

Warfare agent

In addition to their use in medicine, fentanyl derivatives were also examined for their usefulness as chemical warfare agents . Suspicions have been made as to whether a particularly potent fentanyl derivative, carfentanyl , which has not been approved in human medicine , was used in aerosol form in the rescue of the hostages in Moscow's Dubrowka Theater in October 2002 and was one of the causes of 127 deaths from respiratory failure .

A derivative of fentanyl was used by an Israeli Mossad commando in the 1997 assassination attempt on Chalid Maschal in Jordan. Much more potent than fentanyl, it was absorbed through the skin like this (sprayed on the head) and should kill with the appearance of natural death in a few days. The agents were immediately arrested and, under diplomatic pressure, Israel gave the Jordanians the type of active ingredient and the effective antidote ( naloxone ) with instructions on treatment.

Use of fentanyl in executions

Fentanyl was first a drug mixture for as part of the August 14, 2018 execution of double murderer Carey Dean Moore in the state prison of Nebraska used. The reason for the use in lethal injections in the USA is the increasingly difficult procurement of the previously used toxins (including thiopental ) due to a delivery or production stop on the part of the manufacturer. The US state of Nevada was also planning to use fentanyl for executions. After the manufacturer filed a lawsuit against what it believed to be the illegal use of its preparation in July 2018, the execution of Scott Dozier was initially suspended.

Trade names


Abstral (D), Actiq (D, A, CH), Durogesic (D, A, CH), Effentora (D, A), Ernsdolor (A), Fentadolon (D), Fentamed (A), Fentaplast (A), Fentarichtex (A), Fentoron (A), Gelitanyl (A), Ionsys (A), Instanyl (D), Matrifen (D, A), Sintenyl (CH), numerous generics (D, A, CH)


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Web links

Commons : Fentanyl  - collection of pictures, videos and audio files

Individual evidence

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