Carfentanil

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Not to be confused with Carfenil.
Carfentanil
Carfentanil.svg
Clinical data
Trade names Wildnil
ATC code
  • none
Legal status
Legal status
Pharmacokinetic data
Biological half-life 7.7 hrs
Identifiers
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
ChEBI
ChEMBL
Chemical and physical data
Formula C24H30N2O3
Molar mass 394.514 g/mol
3D model (Jmol)
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Carfentanil or carfentanyl (also known as 4-carbomethoxyfentanyl) is an analog of the synthetic opioid analgesic fentanyl. It is 10,000 times more potent than morphine, making it among the most potent commercially used opioids.[1] Carfentanil was first synthesized in 1974 by a team of chemists at Janssen Pharmaceutica which included Paul Janssen.[2] It is marketed under the trade name Wildnil as a general anaesthetic agent for large animals, such as elephants.[3]

Side effects of carfentanil are similar to those of fentanyl, including itching, nausea and respiratory depression, which can be life-threatening. The post-2000 surge in illicit sale and use of fentanyl analogues in Eastern Europe included seizures of carfentanil in Lithuania and Latvia.[4] As of around 2016, carfentanil and other highly potent derivatives of fentanyl started appearing in heroin and were connected to hundreds of overdoses and several deaths in the United States.[5] The extreme toxicity of carfentanil in humans and its ready commercial availability has aroused concerns over its potential use as a weapon of mass destruction by rogue nations and terrorist groups.[6]

Carfentanil is classified as Schedule II under the Controlled Substances Act in the United States with a DEA ACSCN of 9743 and a 2016 annual aggregate manufacturing quota of 19 grams.[7]

Moscow theater hostage crisis[edit]

In 2012, a team of researchers at the British chemical and biological defense laboratories at Porton Down found carfentanil and remifentanil in clothing from two British survivors of the 2002 Moscow theater hostage crisis and urine from a third survivor. The team concluded that the Russian military used an aerosol mist of carfentanil and remifentanil to subdue Chechen hostage takers.[8]

Authors of a previous paper in the Annals of Emergency Medicine 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. Not knowing to expect hundreds of patients exposed to high doses of strong opioids, the emergency workers did not bring enough naloxone or naltrexone (the two most commonly-used opioid antagonists) to counteract the carfentanil and remifentanil and save the lives of many of the victims. 125 people exposed to the gas used in the rescue attempt are confirmed to have died from both respiratory failure and aerosol inhalation during the incident. The authors state that, assuming carfentanil and remifentanil were the only active ingredients of the knockout gas, that the worst danger to the theater victims would have been apnea (loss of breathing), and that mechanical ventilation and/or treatment with opioid antagonists could have saved many lives.[9]

Importation from China and increase in illicit use[edit]

According to an Associated Press article, "Chemical weapon for sale: China's unregulated narcotic", fentanyl, carfentanil and other highly potent derivatives of fentanyl are actively marketed by several Chinese chemical companies. Carfentanil is not a controlled substance in China, where it is manufactured legally and sold openly over the Internet.

Authorities in Latvia and Lithuania have reported seizing carfentanil as an illicit drug in the early 2000s.[6] Around 2016, the US and Canada started reporting a dramatic increase in shipment of carfentanil and other strong opioid drugs to customers in North America from Chinese chemical supply firms. In June, 2016 the Royal Canadian Mounted Police seized one kilogram of carfentanil shipped from China in a box labelled "printer accessories". According to the Canada Border Services Agency, the shipment contained 50 million lethal doses of the drug, more than enough carfentanil to wipe out the entire population of the country, in containers labeled as toner cartridges for Hewlett-Packard LaserJet printers. Allan Lai, an officer-in-charge at the Royal Canadian Mounted Police in Calgary who helped oversee the criminal investigation said, "With respect to carfentanil, we don't know why a substance of that potency is coming into our country."[6]

An article in Time, "Heroin Is Being Laced With a Terrifying New Substance: What to Know About Carfentanil", reports over 300 cases of carfentanil overdose and several deaths connected to the drug since August 2016 in several of the United States, including Ohio, West Virginia, Indiana, Kentucky and Florida.[5] In 2017, a Milwaukee, Wisconsin man died from a carfentanil overdose, likely taken unknowingly with another illegal drug such as heroin or cocaine.[10] Carfentanil is most often taken with heroin or by users who believe they are taking heroin. Carfentanil is added to or sold as heroin because it's less expensive, easier to get (Chinese firms advertise and sell carfentanil over the Internet, offering advice to customers in other countries on how to import it illegally) and easier to make than genuine heroin.[6]

Potential as a chemical weapon[edit]

The toxicity of carfentanil has been compared to that of nerve gas, according to the Associated Press' article "Chemical weapon for sale: China's unregulated narcotic". The article quoted Andrew C. Weber, Assistant US Secretary of Defense for Nuclear, Chemical and Biological Defense Programs from 2009 to 2014, as saying "It's a weapon. Companies shouldn't be just sending it to anybody." Mr. Weber added "Countries that we are concerned about were interested in using it for offensive purposes... We are also concerned that groups like ISIS could order it commercially." Mr. Weber described various ways carfentanil could be used as a weapon, such as knocking troops out and taking them hostage or killing civilians in closed spaces such as train stations.[6]

See also[edit]

References[edit]

  1. ^ "Fentanyl drug profile". EMCDDA. 
  2. ^ Stanley, Theodore H.; Egan, Talmage D.; Aken, Hugo Van (February 2008). "A Tribute to Dr. Paul A. J. Janssen: Entrepreneur Extraordinaire, Innovative Scientist, and Significant Contributor to Anesthesiology". Anesthesia & Analgesia. 106 (2): 451–462. doi:10.1213/ane.0b013e3181605add. PMID 18227300. 
  3. ^ Vos, V. De (22 July 1978). "Immobilisation of free-ranging wild animals using a new drug". Veterinary Record. 103 (4): 64–68. doi:10.1136/vr.103.4.64. ISSN 2042-7670. PMID 685103. 
  4. ^ Mounteney, Jane; Giraudon, Isabelle; Denissov, Gleb; Griffiths, Paul (July 2015). "Fentanyls: Are we missing the signs? Highly potent and on the rise in Europe". International Journal of Drug Policy. 26 (7): 626–631. doi:10.1016/j.drugpo.2015.04.003. PMID 25976511. 
  5. ^ a b Sanburn, Josh. "Heroin Is Being Laced With a Terrifying New Substance". TIME.com. Retrieved 2016-11-24. 
  6. ^ a b c d e Kinetz, Erika; Butler, Desmond (7 October 2016). "Chemical weapon for sale: China's unregulated narcotic". AP News. New York, NY 10281 USA. The Associated Press. Retrieved 12 April 2016. 
  7. ^ "Established Aggregate Production Quotas for Schedule I and II Controlled Substances and Assessment of Annual Needs for the List I Chemicals Ephedrine, Pseudoephedrine, and Phenylpropanolamine for 2016". Federal Register. 6 October 2015. 
  8. ^ 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. 
  9. ^ Wax, Paul M.; Becker, Charles E.; Curry, Steven C. (May 2003). "Unexpected "gas" casualties in Moscow: A medical toxicology perspective". Annals of Emergency Medicine. 41 (5): 700–705. doi:10.1067/mem.2003.148. PMID 12712038. 
  10. ^ Stephenson, Crocker (17 April 2017). "Carfentanil, 10,000 times more potent than morphine, kills homeless man in Milwaukee". Milwaukee Journal Sentinel. Retrieved 17 April 2017.