3-Allylfentanyl

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

3-Allylfentanyl

Legal status
Legal status	US: Schedule I[1]
Identifiers
IUPAC name N-[(3S,4R)-1-Phenethyl-3-prop-2-enylpiperidin-4-yl]-N-phenylpropanamide
CAS Number	86151-80-6 Y
PubChem CID	133866
ChemSpider	118047 Y
UNII	V990X77S2I
Chemical and physical data
Formula	C25H32N2O
Molar mass	376.544 g·mol−1
3D model (JSmol)	Interactive image
SMILES O=C(N(c1ccccc1)[C@@H]3CCN(CCc2ccccc2)C[C@@H]3C\C=C)CC
InChI 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 Y Key:BZXKQFFMDLTPJL-LADGPHEKSA-N Y
NY (what is this?)  (verify)

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

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

• 3-Methylbutyrfentanyl
• 4-Fluorofentanyl
• α-Methylfentanyl
• Acetylfentanyl
• Butyrfentanyl
• List of fentanyl analogues