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Fentanyl (Molecule of the Month for June 2007)

Sublimaze, Duragesic, Actiq



Fentanyl is an opioid and is extensively used for anesthesia and analgesia, most often in the operating room and intensive care unit. It was first synthesized by Janssen Pharmaceutica (Belgium) in the late 1950s, and has an analgesic potency of about 80 times that of morphine. Fentanyl is frequently given intrathecally as part of spinal anesthesia or epidurally for epidural anesthesia and analgesia. Duragesic, by Janssen Pharmaceutica, is a fentanyl transdermal patch used in chronic pain management. Duragesic patches work by releasing fentanyl into body fats, which then slowly release the drug into the blood stream over 72 hours, allowing for long lasting relief from pain. Actiq, by Cephalon, is a recently-developed solid formulation of fentanyl citrate on a stick in the form of a lollipop that dissolves slowly in the mouth for transmucosal absorption. Actiq is intended for opioid-tolerant individuals and is effective in treating breakthrough cancer pain. It is also useful for breakthrough pain for those suffering bone injuries, severe back pain, neuropathy, arthritis, and some other examples of chronic nonmalignant pain. Like other lipid soluble drugs, the pharmacokinetics of fentanyl are poorly understood.

On 26th October 2002 Russian special forces used Fentanyl to end the siege of the theatre building in Moscow where Chechen separatists have been holding hundreds of hostages. At least 119 civilians died in the storming of the theatre, where about 50 armed Chechens were holding almost 800 people hostage, with 245 hospitalized. Russian Health Minister Yuri Shevchenko lifted a veil of official secrecy about the gas following pressure from Western governments, whose citizens were among the hundreds of hostages poisoned by the gas. The minister stressed that the fentanyl gas, widely used in medical practice, "cannot in itself be called lethal". He attributed the hostage deaths to the use of the chemical compound on people who were in a poor condition after three days of captivity - dehydrated, hungry, lacking oxygen and suffering acute stress.

In the United States, fentanyl is a Schedule II drug. Illicit use of pharmaceutical fentanyls first appeared in the mid-1970s in the medical community and continues in the present. United States authorities classify fentanyl as a narcotic. To date, over 12 different analogues of fentanyl have been produced clandestinely and identified in the U.S. drug traffic. The biological effects of the fentanyls are similar to those of heroin, with the exception that there is less of a euphoric 'high' associated with the drug and a stronger analgesic effect. Additionally, fentanyl may be hundreds of times more potent though in some places, it is sold as heroin, often leading to overdoses. In December 2006, a mix of fentanyl and either cocaine or heroin has caused an outbreak in overdose deaths in the United States

Formal Chemical Name (IUPAC)
N-(1-(2-phenylethyl)-4-piperidinyl)-N-phenyl-propanamide

References

http://en.wikipedia.org/wiki/Fentanyl

http://news.bbc.co.uk/1/hi/world/europe/2377563.stm

Picture of Fentanyl 3D model

click on the picture of  Fentanyl above to interact
with the 3D model of the
Fentanyl structure
(this will open a new browser window)

Picture of Fentanyl

C22 H28 N2 O



Update by Karl Harrison
(Molecule of the Month for June 2007 )

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