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Carfentanil

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Carfentanil
Clinical data
Trade namesWildnil
ATC code
  • none
Legal status
Legal status
Pharmacokinetic data
Elimination half-life7.7 hrs
Identifiers
  • 4-((1-oxopropyl)-phenylamino)-1-(2-phenylethyl)-4-piperidinecarboxylic acid methyl ester
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.352.183 Edit this at Wikidata
Chemical and physical data
FormulaC24H30N2O3
Molar mass394.514 g/mol g·mol−1
3D model (JSmol)
  • O=C(C1(CCN(CC1)CCC2=CC=CC=C2)N(C(CC)=O)C3=CC=CC=C3)OC
  • InChI=1S/C24H30N2O3/c1-3-22(27)26(21-12-8-5-9-13-21)24(23(28)29-2)15-18-25(19-16-24)17-14-20-10-6-4-7-11-20/h4-13H,3,14-19H2,1-2H3 checkY
  • Key:YDSDEBIZUNNPOB-UHFFFAOYSA-N checkY
  (verify)

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.[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.[3]

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.[4]

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.[5]

In 2016, carfentanil was identified as an additive in heroin sold in Ohio, leading to a spike in the number of overdose cases.[6]

Moscow theater hostage crisis

Main article: 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.[7][8] Its short action, easy reversibility and therapeutic index (10,600 vs. 300 for fentanyl)[citation needed] 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.

See also

References

  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. ^ "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.
  6. ^ Sanburn, Josh. "Heroin Is Being Laced With a Terrifying New Substance". TIME.com. Retrieved 2016-11-24.
  7. ^ 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.
  8. ^ 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.
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