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3-Allylfentanyl

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3-Allylfentanyl
Legal status
Legal status
Identifiers
  • N-[(3S,4R)-1-Phenethyl-3-prop-2-enylpiperidin-4-yl]-N-phenylpropanamide
CAS Number
PubChem CID
ChemSpider
UNII
Chemical and physical data
FormulaC25H32N2O
Molar mass376.544 g·mol−1
3D model (JSmol)
  • O=C(N(c1ccccc1)[C@@H]3CCN(CCc2ccccc2)C[C@@H]3C\C=C)CC
  • InChI=1S/C25H32N2O/c1-3-11-22-20-26(18-16-21-12-7-5-8-13-21)19-17-24(22)27(25(28)4-2)23-14-9-6-10-15-23/h3,5-10,12-15,22,24H,1,4,11,16-20H2,2H3/t22-,24+/m0/s1 checkY
  • Key:BZXKQFFMDLTPJL-LADGPHEKSA-N checkY
 ☒NcheckY (what is this?)  (verify)

3-Allylfentanyl is an opioid analgesic that is an analogue of fentanyl.

3-Allylfentanyl[2] has effects similar to fentanyl, although it is only 0.13x-0.14x as potent by weight.[3]

The decreased potency of this analogue caused by the addition of the allyl group makes it somewhat less dangerous than fentanyl itself (ED50(rat) of 80μg/kg vs 11μg/kg for fentanyl), although this is relative.[3] For comparison, carfentanil is at least 20-30x as potent as fentanyl.

Side Effects

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Side effects of fentanyl analogs vary based on strength and are similar to those of fentanyl itself, which include itching, nausea and potentially serious respiratory depression, which can be life-threatening.

See also

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References

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  1. ^ Drug Enforecement Administration, Department of Justice (February 2018). "Schedules of Controlled Substances:Temporary Placement of Fentanyl-Related Substances in Schedule I. Temporary amendment; temporary scheduling order". Federal Register. 83 (25): 5188–92. PMID 29932611.
  2. ^ US Expired USRE33495E, Linas V. Kudzma, H. Kenneth Spencer, Sherry A. Savernak, "Stereoselective preparation of 3-substituted-4-anilino-piperidine compounds and derivatives", published 1990-12-18, issued 1990-12-18, assigned to Anaquest, INC. A DE Corporation 
  3. ^ a b Casy AF, Ogungbamila FO (March 1982). "3-Allyl analogues of fentanyl". The Journal of Pharmacy and Pharmacology. 34 (3): 210. doi:10.1111/j.2042-7158.1982.tb04229.x. PMID 6121908. S2CID 41011062.