3-Allylfentanyl

3-Allylfentanyl
Legal status
Legal status	US: Schedule I;
Identifiers
	IUPAC name N-[(3S,4R)-1-Phenethyl-3-prop-2-enylpiperidin-4-yl]-N-phenylpropanamide;
CAS Number	86151-80-6 ;
PubChem CID	133866;
ChemSpider	118047 ;
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 ; Key:BZXKQFFMDLTPJL-LADGPHEKSA-N ;
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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

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.

References

^ 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.
^ 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
^ ^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.

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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

[pmid6121908-3] 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.

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Side Effects

See also

References