|Biological half-life||7.7 hrs|
IUPAC name: 4-((1-oxopropyl)-phenylamino)-1-(2-phenylethyl)-4-piperidinecarboxylic acid methyl ester
|Chemical and physical data|
|Molar mass||394.514 g/mol|
|3D model (Jmol)||Interactive image|
Carfentanil or carfentanyl (also known as 4-carbomethoxyfentanyl) is an analog of the synthetic opioid analgesic fentanyl. It was found to be four orders of magnitude or 10,000 times more potent than morphine, making it one of the most potent known and the most potent commercially used opioids. Carfentanil was first synthesized in 1974 by a team of chemists at Janssen Pharmaceutica which included Paul Janssen. It is marketed under the trade name Wildnil as a general anaesthetic agent for large animals.
Side effects of fentanyl analogs are similar to those of fentanyl itself, which include itching, nausea and potentially serious respiratory depression, which can be life-threatening. Fentanyl analogs have killed hundreds of people throughout Europe and the former Soviet republics since the most recent resurgence in use began in Estonia in the early 2000s, and novel derivatives continue to appear.
Carfentanil is a Schedule II Narcotic controlled substance in the United States with a DEA ACSCN of 9743 and a 2016 annual aggregate manufacturing quota of 19 grams, unchanged from the prior year.
In 2016, carfentanil was identified as an additive in heroin sold in Ohio, leading to a spike in the number of overdose cases.
Moscow theater hostage crisis
A 2012 study found evidence supporting the claim that during the 2002 Moscow theater hostage crisis, the Russian military made use of an aerosol form of carfentanil and another similar drug, remifentanil, to subdue Chechen hostage takers. Its short action, easy reversibility and therapeutic index (10,600 vs. 300 for fentanyl) would make it a potential agent for this purpose. Riches, et al., found evidence from liquid chromatography-tandem mass spectrometry analysis of extracts of clothing from two British survivors, and urine from a third survivor, that the aerosol contained a mixture of the two anesthetics, the exact proportions of which the study was unable to determine. Previously, Wax et al. had surmised from the available evidence that the Moscow emergency services had not been informed of the use of the agent, but were instructed to bring opioid antagonists. Because of the lack of information provided, the emergency workers did not bring adequate supplies of naloxone (opioid inverse agonist) or naltrexone (opioid antagonist) to prevent complications in many of the victims and there were subsequently over 125 confirmed deaths from both respiratory failure and aerosol inhalation during the incident. Assuming that carfentanil and remifentanil were the only active constituents, which has not been verified by the Russian military, the primary acute toxic effect to the theater victims would have been opioid-induced apnea; in this case mechanical ventilation or treatment with opioid antagonists could have been life-saving for many victims.
- Lofentanil (3-Methylcarfentanyl)
- Opioid comparison
- R-30490 (4-Methoxymethylfentanyl)
- "Fentanyl drug profile". EMCDDA.
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- Riches, James R.; Read, Robert W.; Black, Robin M.; Cooper, Nicholas J.; Timperley, Christopher M. (November 2012). "Analysis of Clothing and Urine from Moscow Theatre Siege Casualties Reveals Carfentanil and Remifentanil Use". Journal of Analytical Toxicology. 36 (9): 647–656. doi:10.1093/jat/bks078. ISSN 1945-2403. PMID 23002178.
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