Furanylfentanyl

Furanylfentanyl (Fu-F) is an opioid analgesic that is an analog of fentanyl^[1] and has been sold as a designer drug.^[2][3] It has an ED₅₀ value of 0.02 mg/kg in mice.^[4] This makes it approximately one fifth as potent as fentanyl.^[5]

Furanylfentanyl

Clinical data
ATC code	none
Legal status
Legal status	BR: Class F1 (Prohibited narcotics) CA: Schedule I DE: Anlage II (Authorized trade only, not prescriptible) UK: Under Psychoactive Substances Act US: Schedule I UN: Narcotic Schedule I Illegal in Sweden
Identifiers
IUPAC name N-Phenyl-N-[1-(2-phenylethyl)piperidin-4-yl]furan-2-carboxamide
CAS Number	101345-66-8
PubChem CID	13653606
ChemSpider	14921702
UNII	3F7C9J1LS7
KEGG	C22761
CompTox Dashboard (EPA)	DTXSID601032311
Chemical and physical data
Formula	C24H26N2O2
Molar mass	374.484 g·mol−1
3D model (JSmol)	Interactive image
SMILES O=C(N(C1CCN(CC1)CCc2ccccc2)c3ccccc3)c4occc4
InChI InChI=1/C24H26N2O2/c27-24(23-12-7-19-28-23)26(21-10-5-2-6-11-21)22-14-17-25(18-15-22)16-13-20-8-3-1-4-9-20/h1-12,19,22H,13-18H2 Key:FZJVHWISUGFFQV-UHFFFAOYSA-N

Side effects

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.^[6]

Life-threatening adverse reactions caused by furanylfentanyl use have been observed in Sweden^[7] and Canada.^[8] At least seven deaths in Cook County, Illinois, have been linked to furanylfentanyl in 2016, with additional deaths in suburban Chicago in 2017.^[9][10][11]

Detection in biological fluids

Furanylfentanyl may be measured in blood or urine to monitor for use, confirm a diagnosis of poisoning, or assist in a medicolegal death investigation. Commercially available immunoassays are often used as initial screening tests, but chromatographic techniques are generally used for confirmation and quantitation. Blood furanylfentanyl concentrations are expected to be in a range of 1-45 μg/L in victims of fatal overdosage.^[12][13][14]

Legal status

Furanylfentanyl is illegal in Sweden as of January 2016.^[15]

The United States Drug Enforcement Administration (DEA) proposed a temporary placement of furanylfentanyl into Schedule I of the Controlled Substances Act on 27 September 2016.^[16] On November 29, 2016, the DEA issued its final rule, making furanylfentanyl Schedule I.^[17][18]

See also

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

References

1. Bagley JR, Wynn RL, Rudo FG, Doorley BM, Spencer HK, Spaulding T (March 1989). "New 4-(heteroanilido)piperidines, structurally related to the pure opioid agonist fentanyl, with agonist and/or antagonist properties". Journal of Medicinal Chemistry. 32 (3): 663–671. doi:10.1021/jm00123a028. PMID 2563773.
2. Kanamori T, Okada Y, Segawa H, Yamamuro T, Kuwayama K, Tsujikawa K, Togawa-Iwata Y (August 2020). "Detection and confirmation of the ring-opened carboxylic acid metabolite of a new synthetic opioid furanylfentanyl". Forensic Toxicology. 39: 114–122. doi:10.1007/s11419-020-00546-7. ISSN 1860-8973.
3. 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.
4. Huang BS, Terrell RC, Deutsche KH, Kudzma LV, Lalinde NL (9 April 1984). "Patent US4584303 - N-aryl-N-(4-piperidinyl)amides and pharmaceutical compositions and method employing such compounds". The Boc Group, Inc.
5. Chen Q, Shang Y, Xu Y, Li P, Li P, Liu GL (February 2016). "Analgesic effect and pharmacological mechanism of fentanyl and butorphanol in a rat model of incisional pain". Journal of Clinical Anesthesia. 28: 67–73. doi:10.1016/j.jclinane.2015.08.010. PMID 26440441.
6. Mounteney J, Giraudon I, Denissov G, Griffiths P (July 2015). "Fentanyls: Are we missing the signs? Highly potent and on the rise in Europe". The International Journal on Drug Policy. 26 (7): 626–631. doi:10.1016/j.drugpo.2015.04.003. PMID 25976511.
7. Helander A, Bäckberg M, Beck O (20 April 2016). "Intoxications involving the fentanyl analogs acetylfentanyl, 4-methoxybutyrfentanyl and furanylfentanyl: results from the Swedish STRIDA project". Clinical Toxicology. 54 (4): 324–332. doi:10.3109/15563650.2016.1139715. PMID 26850293. S2CID 41668288.
8. Klar SA, Brodkin E, Gibson E, Padhi S, Predy C, Green C, Lee V (September 2016). "Notes from the Field: Furanyl-Fentanyl Overdose Events Caused by Smoking Contaminated Crack Cocaine - British Columbia, Canada, July 15-18, 2016". MMWR. Morbidity and Mortality Weekly Report. 65 (37): 1015–1016. doi:10.15585/mmwr.mm6537a6. PMID 27657853.
9. Preckwinkle T (18 April 2016). "Medical Examiner Reports Deaths from Powerful Opioids on the Rise". Cook County Government. Archived from the original on 2016-06-02.
10. Mohr AL, Friscia M, Papsun D, Kacinko SL, Buzby D, Logan BK (November 2016). "Analysis of Novel Synthetic Opioids U-47700, U-50488 and Furanyl Fentanyl by LC-MS/MS in Postmortem Casework". Journal of Analytical Toxicology. 40 (9): 709–717. doi:10.1093/jat/bkw086. PMID 27590036.
11. Marrazzo A. "New form of synthetic heroin showing up in Chicago-area deaths". McHenry County. Retrieved 2017-02-04.
12. Baselt, R. (2017) Disposition of Toxic Drugs and Chemicals in Man, 11th edition, Biomedical Publications, Foster City, CA, p. 2315.
13. Mohr AL, Friscia M, Papsun D, Kacinko SL, Buzby D, Logan BK (November 2016). "Analysis of Novel Synthetic Opioids U-47700, U-50488 and Furanyl Fentanyl by LC-MS/MS in Postmortem Casework". Journal of Analytical Toxicology. 40 (9): 709–717. doi:10.1093/jat/bkw086. PMID 27590036.
14. Dybowski MP, Dawidowicz AL (January 2020). "Furanylfentanyl in whole blood measured by GC–MS/MS after QuEChERS extraction in a fatal case". Forensic Toxicology. 38 (2): 496–504. doi:10.1007/s11419-019-00515-9. ISSN 1860-8973. S2CID 209897483.
15. "31 nya ämnen kan klassas som narkotika eller hälsofarlig vara" (in Swedish). Folkhälsomyndigheten. 17 November 2015.
16. Drug Enforcement Administration (DEA) (27 September 2016). "Proposed Rule: Schedules of Controlled Substances: Temporary Placement of Furanyl Fentanyl Into Schedule I". Federal Register.
17. "2016 - Final Order: Temporary Placement of Furanyl Fentanyl Into Schedule I". www.deadiversion.usdoj.gov.
18. Kroll D. "Furanyl Fentanyl Joins U-47,700 As The Second Illicit Opioid Banned By DEA In November". forbes.com.