Carfentanil

Source: Wikipedia, the free encyclopedia.
Not to be confused with
Carfenil
.

Carfentanil
Clinical data
Trade namesWildnil
Other names(4-Methoxycarbonyl)fentanyl, R-33799
AHFS/Drugs.comInternational Drug Names
ATC code
  • None
Legal status
Legal status
Pharmacokinetic data
Elimination half-life7.7 hours
Identifiers
  • Methyl 1-(2-phenylethyl)-4-[phenyl(propanoyl)amino]piperidine-4-carboxylate
JSmol)
  • CCC(=O)N(c1ccccc1)C2(C(=O)OC)CCN(CC2)CCc3ccccc3
  • 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, sold under the brand name Wildnil, is an extremely

inhalation.[1] Deaths have been reported in association with carfentanil.[1][2]

Effects and

synthetic opioid analgesic fentanyl.[4] It acts as an ultrapotent and highly selective agonist of the μ-opioid receptor.[1]

Carfentanil was first synthesized in 1974 by a team of chemists at Janssen Pharmaceuticals which included Paul Janssen.[5] It was introduced into veterinary medicine in 1986.[1] Carfentanil is legally controlled in most jurisdictions.[2]

Uses

Veterinary use

Chosen for its high

compounded form.[7] Since then, etorphine has become the standard tranquilizing agent for large mammals, with diprenorphine as the preferred reversal agent. Diprenorphine was also used previously to reverse the effects of carfentanil.[8]

Clinical use

Carfentanil has been used at doses of less than 7 μg as a

radiotracer for positron emission tomography imaging of the μ-opioid receptor in the brain in humans.[1]

Pharmacology

Pharmacodynamics

Carfentanil acts as a highly

analgesic potency of morphine, 4,000 times the potency of heroin, and 20 to 100 times the potency of fentanyl in animal studies.[10][1][2] The effects of carfentanil are reversed by μ-opioid receptor antagonists like naloxone and naltrexone, though higher than normal doses of these agents may be necessary in humans due to the extremely high potency of carfentanil.[1][2]

Pharmacokinetics

A

norcarfentanil were estimated to be 5.7 hours and 11.8 hours, respectively.[1][11]

Chemistry

Nomenclature for derivatives of fentanyl

Carfentanil is an

phenylfentanyl, lofentanil (3‑methylcarfentanyl), N-Methylnorcarfentanil, R-30490 (4‑methoxymethylfentanyl), sufentanil, and thiafentanil
.

History

Increase in illicit use

See also: Gray death
US penny
is 19.05 mm, or 0.75 inches.

Over three hundred cases of overdose related to fentanyl and fentanyl analogues were reported between August and November 2016 in several of the United States, including Ohio, West Virginia, Indiana, Kentucky and Florida.[15] In 2017, a Milwaukee, Wisconsin, man died from a Carfentanil overdose, likely taken unknowingly with another illegal drug such as heroin or cocaine.[16] In 2022, 71,269 fatal overdose victims tested positive for Carfentanil.[17] 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 is less expensive, easier to obtain, and easier to manufacture than heroin.[18]

Importation from China

Authorities in Latvia and Lithuania reported seizing Carfentanil as an illicit drug in the early 2000s.[18][19]

Around 2016, the United States and Canada reported 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 labeled "printer accessories". According to the Canada Border Services Agency, the shipment contained 50 million potentially lethal doses of the drug, in containers labeled as toner cartridges for HP LaserJet printers.[18]

Carfentanil was not a controlled substance in China until 1 March 2017,[20] and until then was manufactured legally and sold openly over the Internet, being actively marketed by several Chinese chemical companies.[18]

Moscow theater hostage crisis

Main article: Moscow theater hostage crisis

In 2012, a team of researchers at the British chemical and biological defence laboratories at

emergency services had not been informed of the use of the agent, despite being instructed to bring opioid antagonists to the scene. Unaware that hundreds of patients had been exposed to high doses of strong opioids, the emergency workers failed to bring sufficient quantities of naloxone and naltrexone to counteract the effects of carfentanil and remifentanil. One hundred twenty-five people exposed to the aerosol are confirmed to have died from respiratory failure during the incident.[22]

Potential as a chemical weapon

The toxicity of carfentanil in humans and its ready commercial availability has raised concerns over its potential use as a chemical

terrorist groups. The toxicity of carfentanil has been compared to that of nerve gas.[18]

Society and culture

Legal status

China

Carfentanil has been controlled in China since 1 March 2017.[3]: 21  The trade war between China and the United States has included controversy over the effectiveness of this control.[23][24][25]

Germany

Carfentanil and its

Anlage I
substance and can only be used with the special permission of the authorities.

United States

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 (less than 0.7 oz.).[26] Carfentanil has been manufactured under the brand-name Wildnil by Wildlife Laboratories Inc.[27] Wildlife Laboratories Inc. is also the manufacturer of diprenorphine and etorphine for veterinary use.

United Kingdom

Carfentanil has been specifically controlled as a Class A drug since 1986.[28]

See also

References

  1. ^
    S2CID 231918983
    .
  2. ^
    PMID 29367860
    .
  3. ^ a b c d "Report on the risk assessment of methyl 1-(2-phenylethyl)-4-[phenyl(propanoyl) amino]piperidine-4-carboxylate in the framework of the Council Decision on new psychoactive substances" (PDF). European Monitoring Centre for Drugs and Drug Addiction. 8 July 2018.
  4. ^ "Fentanyl drug profile". EMCDDA.
  5. ^
    S2CID 20490363
    .
  6. JSTOR 20094842
    .
  7. ^ "Carfentanil Critical Review Report" (PDF). World Health Organisation. Retrieved 3 September 2018.
  8. PMID 30456980
    .
  9. ^
    S2CID 30414509
    .
  10. ^
    S2CID 58642995
    .
  11. S2CID 5029164
    .
  12. ^ "Fentanyl. Image 4 of 17". Drug Enforcement Administration.
  13. ^ "DEA Issues Carfentanil Warning To Police And Public". United States Drug Enforcement Administration. 22 September 2016. The lethal dose range for carfentanil in humans is unknown
  14. PMID 30416445
    . 26 October 2018. From the conclusion: "Postmortem concentrations seemed to correlate with their potency, although the presence of other CNS depressants, such as ethanol and benzodiazepines has to be taken into account."
  15. ^ Sanburn J. "Heroin Is Being Laced With a Terrifying New Substance". Time. Retrieved 24 November 2016.
  16. ^ Stephenson C (17 April 2017). "Carfentanil, 10,000 times more potent than morphine, kills homeless man in Milwaukee". Milwaukee Journal Sentinel. Retrieved 17 April 2017.
  17. ^ "Drug Overdoses - Data Details - Injury Facts".
  18. ^ a b c d e Kinetz E, Butler D (7 October 2016). "Chemical weapon for sale: China's unregulated narcotic". AP News. New York, NY. The Associated Press. Archived from the original on 30 July 2018. Retrieved 12 April 2016.
  19. PMID 25976511
    .
  20. ^ "China makes deadly opioid carfentanil a controlled substance". Associated Press via theday.com. 15 February 2017. Retrieved 29 July 2019.
  21. PMID 23002178
    .
  22. S2CID 44761840
    .
  23. ^ Bernstein L (3 October 2018). "Drug trade war: Chinese fentanyl is fueling the US opioid crisis". WJLA. Retrieved 25 August 2020.
  24. ^ Landay J (2 August 2019). "Trump accuses China's Xi of failing to halt fentanyl exports to U.S." Reuters. Retrieved 25 August 2020.
  25. ^ Myers SL (1 December 2019). "China Cracks Down on Fentanyl. But Is It Enough to End the U.S. Epidemic?". The New York Times. Retrieved 25 August 2020.
  26. ^ "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.
  27. S2CID 231918983
    .
  28. ^ "Misuse of Drugs Act 1971 (c. 38): SCHEDULE 2: Controlled Drugs". Office of Public Sector Information. Retrieved 15 June 2009.
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