Acrylfentanyl

Acrylfentanyl
Clinical data
ATC code
  • None
Legal status
Legal status
Identifiers
  • N-Phenyl-N-[1-(2-phenylethyl)piperidin-4-yl]prop-2-enamide
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC22H26N2O
Molar mass334.463 g·mol−1
3D model (JSmol)
  • C=CC(=O)N(c2ccccc2)C1CCN(CC1)CCc3ccccc3

  • HCl: C=CC(=O)N(c2ccccc2)C1CCN(CC1)CCc3ccccc3.Cl
  • 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.[1][2][3][4][5] In animal studies the IC50 (the 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.[6][7][8][9]

  1. ^ "Acrylfentanyl (hydrochloride)". Cayman Chemical.
  2. ^ Ujváry I, Jorge R, Christie R, Le Ruez T, Danielsson HV, Kronstrand R, Elliott S, Gallegos A, Sedefov R, Evans-Brown M (July 2017). "Acryloylfentanyl, a recently emerged new psychoactive substance: a comprehensive review". Forensic Toxicology. 35 (2): 232–243. doi:10.1007/s11419-017-0367-8. S2CID 30184205.
  3. ^ Breindahl T, Kimergård A, Andreasen MF, Pedersen DS (March 2017). "Identification of a new psychoactive substance in seized material: the synthetic opioid N-phenyl-N-[1-(2-phenethyl)piperidin-4-yl]prop-2-enamide (Acrylfentanyl)". Drug Testing and Analysis. 9 (3): 415–422. doi:10.1002/dta.2046. PMC 5396312. PMID 27476446.
  4. ^ Helander A, Bäckberg M (January 2017). "New Psychoactive Substances (NPS) - the Hydra monster of recreational drugs". Clinical Toxicology. 55 (1): 1–3. doi:10.1080/15563650.2016.1217003. PMID 27549399. S2CID 35645218.
  5. ^ Bilel S, Azevedo Neto J, Arfè R, Tirri M, Gaudio RM, Fantinati A, et al. (May 2022). "In vitro and in vivo pharmaco-dynamic study of the novel fentanyl derivatives: Acrylfentanyl, Ocfentanyl and Furanylfentanyl". Neuropharmacology. 209: 109020. doi:10.1016/j.neuropharm.2022.109020. hdl:11392/2497907. PMID 35247453. S2CID 247172069.
  6. ^ Maryanoff BE, Simon EJ, Gioannini T, Gorissen H (August 1982). "Potential affinity labels for the opiate receptor based on fentanyl and related compounds". Journal of Medicinal Chemistry. 25 (8): 913–919. doi:10.1021/jm00350a006. PMID 6288945.
  7. ^ Dong N, Lu WC, Chen NY, Zhu YC, Chen KX (January 2005). "Using support vector classification for SAR of fentanyl derivatives". Acta Pharmacologica Sinica. 26 (1): 107–112. doi:10.1111/j.1745-7254.2005.00014.x. PMID 15659122.
  8. ^ Essawi MY (April 1999). "Fentanyl analogues with a modified propanamido group as potential affinity labels: synthesis and in vivo activity". Die Pharmazie. 54 (4): 307–308. PMID 10234745.
  9. ^ Zhu YQ, Ge GL, Fang SN, Zhu YC, Dai QY, Tan ZY, et al. (March 1981). "[Studies on potent analgesics. I. Synthesis and analgesic activity of derivatives of fentanyl (author's transl)]". Yao Xue Xue Bao = Acta Pharmaceutica Sinica (in Chinese). 16 (3): 199–210. PMID 6264735.