Trefentanil

Trefentanil (A-3665) is an opioid analgesic that is an analogue of fentanyl and was developed in 1992.[1]

Trefentanil
Clinical data
ATC code
  • none
Identifiers
IUPAC name
  • N-{1-[2-(4-ethyl-5-oxo-4,5-dihydro-1H-tetrazol-1-yl)ethyl]-4-phenylpiperidin-4-yl}-N-(2-fluorophenyl)propanamide
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC25H31FN6O2
Molar mass466.561 g·mol−1
3D model (JSmol)
SMILES
  • Fc1ccccc1N(C(=O)CC)C4(c2ccccc2)CCN(CCN3\N=N/N(C3=O)CC)CC4
InChI
  • InChI=1S/C25H31FN6O2/c1-3-23(33)32(22-13-9-8-12-21(22)26)25(20-10-6-5-7-11-20)14-16-29(17-15-25)18-19-31-24(34)30(4-2)27-28-31/h5-13H,3-4,14-19H2,1-2H3 Y
  • Key:RJSCINHYBGMIFT-UHFFFAOYSA-N Y
 NY (what is this?)  (verify)

Trefentanil is most similar to short-acting fentanyl analogues such as alfentanil. In comparative studies, trefentanil was slightly more potent and shorter acting than alfentanil as an analgesic,[2] but induced significantly more severe respiratory depression.[1] For this reason trefentanil has not been adopted for clinical use, although it is still used in research.

Trefentanil has very similar effects to alfentanil, much like those of fentanyl itself but more potent and shorter lasting. 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 trefentanil, and these drugs pose a significant risk of death if used outside of a hospital setting with appropriate artificial breathing apparatus available.

References
  1. Cambareri JJ, Afifi MS, Glass PS, Esposito BF, Camporesi EM (April 1993). "A-3665, a new short-acting opioid: a comparison with alfentanil". Anesthesia and Analgesia. 76 (4): 812–6. doi:10.1213/00000539-199304000-00023. PMID 8466023. S2CID 22230595.
  2. Lemmens HJ, Dyck JB, Shafer SL, Stanski DR (September 1994). "Pharmacokinetic-pharmacodynamic modeling in drug development: application to the investigational opioid trefentanil". Clinical Pharmacology and Therapeutics. 56 (3): 261–71. doi:10.1038/clpt.1994.136. PMID 7924121. S2CID 2058962.
  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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