Brifentanil

Opioid analgesic drug
  • none
Identifiers
  • N-[(3R,4S)-1-[2-(4-Ethyl-5-oxotetrazol-1-yl)ethyl] -3-methylpiperidin-4-yl]-N-(2-fluorophenyl)-2-methoxyacetamide
CAS Number
  • 101345-71-5
PubChem CID
  • 60672
ChemSpider
  • 54682 checkY
UNII
  • 6GDT77PQBW
ChEMBL
  • ChEMBL2220476
CompTox Dashboard (EPA)
  • DTXSID20143867 Edit this at Wikidata
Chemical and physical dataFormulaC20H29FN6O3Molar mass420.489 g·mol−13D model (JSmol)
  • Interactive image
  • Fc1ccccc1N(C(=O)COC)[C@H]3CCN(CCN2\N=N/N(C2=O)CC)C[C@H]3C
InChI
  • InChI=1S/C20H29FN6O3/c1-4-25-20(29)26(23-22-25)12-11-24-10-9-17(15(2)13-24)27(19(28)14-30-3)18-8-6-5-7-16(18)21/h5-8,15,17H,4,9-14H2,1-3H3/t15-,17+/m1/s1 checkY
  • Key:KKMGCTVJCQYQPV-WBVHZDCISA-N checkY
  (verify)

Brifentanil (A-3331) is an opioid analgesic that is an analogue of fentanyl and was developed in the early 1990s.[1]

Brifentanil is most similar to highly potent, short-acting fentanyl analogues such as alfentanil. The effects of brifentanil are very similar to those of alfentanil, with strong but short lasting analgesia and sedation, and particularly notable itching and respiratory depression.[2]

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.[3]

References

  1. ^ Lalinde N, Moliterni J, Wright D, Spencer HK, Ossipov MH, Spaulding TC, Rudo FG (October 1990). "Synthesis and pharmacological evaluation of a series of new 3-methyl-1,4-disubstituted-piperidine analgesics". Journal of Medicinal Chemistry. 33 (10): 2876–82. doi:10.1021/jm00172a032. PMID 2170652.
  2. ^ Camporesi EM, Esposito B, Cigada M (September 1991). "[Ventilatory response to hypoxia and hypercapnia after intravenous brifentanyl (a new synthetic narcotic)]". Minerva Anestesiologica (in Italian). 57 (9): 618. PMID 1798508.
  3. ^ Mounteney J, Giraudon I, Denissov G, Griffiths P (July 2015). "Fentanyls: Are we missing the signs? Highly potent and on the rise in Europe". The International Journal on Drug Policy. 26 (7): 626–31. doi:10.1016/j.drugpo.2015.04.003. PMID 25976511.
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