Brifentanil

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

Brifentanil
Clinical data
Other namesBrifentanil
ATC code
  • none
Identifiers
IUPAC name
  • N-[(3R,4S)-1-[2-(4-Ethyl-5-oxotetrazol-1-yl)ethyl] -3-methylpiperidin-4-yl]-N-(2-fluorophenyl)-2-methoxyacetamide
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC20H29FN6O3
Molar mass420.489 g·mol−1
3D model (JSmol)
SMILES
  • 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 Y
  • Key:KKMGCTVJCQYQPV-WBVHZDCISA-N Y
  (verify)

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] The risk of respiratory depression is especially high with potent fentanyl analogues such as alfentanil and brifentanil, and these drugs pose a significant risk of death if used outside of a hospital setting without an appropriate artificial breathing apparatus available.

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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