Acrylfentanyl

Acrylfentanyl

Clinical data
ATC code	None
Legal status
Legal status	CA: Schedule I UK: Class A Illegal in Sweden
Identifiers
IUPAC name N-Phenyl-N-[1-(2-phenylethyl)piperidin-4-yl]prop-2-enamide
CAS Number	82003-75-6 HCl: 79279-03-1
PubChem CID	10314851 HCl: 12782338
ChemSpider	8490316 HCl: 24621155
UNII	T64K7YD33B HCl: QY70U25H9M
ChEMBL	CHEMBL1196205 HCl: CHEMBL556159
Chemical and physical data
Formula	C22H26N2O
Molar mass	334.46 g·mol−1
3D model (JSmol)	Interactive image HCl: Interactive image
SMILES C=CC(=O)N(C1CCN(CC1)CCC2=CC=CC=C2)C3=CC=CC=C3 HCl: C=CC(=O)N(C1CCN(CC1)CCC2=CC=CC=C2)C3=CC=CC=C3.Cl
InChI InChI=1S/C22H26N2O/c1-2-22(25)24(20-11-7-4-8-12-20)21-14-17-23(18-15-21)16-13-19-9-5-3-6-10-19/h2-12,21H,1,13-18H2 Key:RFQNLMWUIJJEQF-UHFFFAOYSA-N HCl: InChI=1S/C22H26N2O.ClH/c1-2-22(25)24(20-11-7-4-8-12-20)21-14-17-23(18-15-21)16-13-19-9-5-3-6-10-19;/h2-12,21H,1,13-18H2;1H Key:YUHNRLIKLNYPDD-UHFFFAOYSA-N

Acrylfentanyl (also known as acryloylfentanyl) is a highly potent opioid analgesic that is an analog of fentanyl and has been sold online as a designer drug. In animal studies the IC₅₀ or half maximal inhibitory concentration for acrylfentanyl to displace naloxone is 1.4 nM, being slightly more potent than fentanyl itself (1.6 nM) as well as having a longer duration of action.

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.

As acrylamide derivatives are often used in drug discovery to make covalent inhibitors which will bind irreversibly to its target, acrylfentanyl is claimed to be naloxone resistant. However, acute intoxications with acrylfentanyl on mice threatened by naloxone (2 mg/kg) have shown that acrylfentanyl could be displaced from the opioid receptor.

Acrylfentanyl has been linked to 20 deaths in Sweden as well as two deaths in Denmark in summer 2016.

As of 16 August 2016, acrylfentanyl is illegal in Sweden.