Tetrahydrofuranylfentanyl

Tetrahydrofuranylfentanyl
Legal status
Legal status	BR: Class F1 (Prohibited narcotics); CA: Schedule I; DE: Anlage II (Authorized trade only, not prescriptible); UK: Class A; US: Schedule I;
Identifiers
	IUPAC name N-Phenyl-N-[1-(2-phenylethyl)piperidin-4-yl]oxolane-2-carboxamide;
CAS Number	2142571-01-3;
PubChem CID	137332293;
UNII	Z3UD65Z8B2;
KEGG	C22758;
CompTox Dashboard (EPA)	DTXSID201036785 ;
Chemical and physical data
Formula	C24H30N2O2
Molar mass	378.516 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES C1(=CC=CC=C1)N(C(=O)C1OCCC1)C1CCN(CC1)CCC1=CC=CC=C1;
	InChI InChI=1S/C24H30N2O2/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/h1-6,8-11,22-23H,7,12-19H2; Key:OHJNHKUFSKAANI-UHFFFAOYSA-N;

Tetrahydrofuranylfentanyl is an opioid analgesic that is an analog of fentanyl and has been sold online as a designer drug, first appearing in Europe in late 2016.^[1]^[2]

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.^[3] A new wave of fentanyl analogues and associated deaths began in around 2014 in the US, and have continued to grow in prevalence; especially since 2016 these drugs have been responsible for hundreds of overdose deaths every week.^[4]

Legal status

Tetrahydrofuranylfentanyl was placed into Schedule I in the US in October 2017, in order to avoid an imminent hazard to public safety.^[5]

References

^ "EMCDDA–Europol Joint Report on a new psychoactive substance: N-phenyl-N-[1-(2-phenylethyl)piperidin-4-yl]tetrahydrofuran-2-carboxamide (tetrahydrofuranylfentanyl; THF-F)". September 2017.
^ Kanamori T, Segawa H, Yamamuro T, Kuwayama K, Tsujikawa K, Iwata YT (April 2020). "Metabolism of a new synthetic opioid tetrahydrofuranylfentanyl in fresh isolated human hepatocytes: Detection and confirmation of ring-opened metabolites". Drug Testing and Analysis. 12 (4): 439–448. doi:10.1002/dta.2743. PMID 31797567. S2CID 208627099.
^ 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.
^ Armenian P, Vo KT, Barr-Walker J, Lynch KL (May 2018). "Fentanyl, fentanyl analogs and novel synthetic opioids: A comprehensive review". Neuropharmacology. 134 (Pt A): 121–132. doi:10.1016/j.neuropharm.2017.10.016. PMID 29042317. S2CID 21404877.
^ Drug Enforcement Administration, Department of Justice (October 2017). "Schedules of Controlled Substances: Temporary Placement of ortho-Fluorofentanyl, Tetrahydrofuranyl Fentanyl, and Methoxyacetyl Fentanyl Into Schedule I. Temporary amendment; temporary scheduling order". Federal Register. 82 (206): 49504–49508. PMID 29091366.

[1] "EMCDDA–Europol Joint Report on a new psychoactive substance: N-phenyl-N-[1-(2-phenylethyl)piperidin-4-yl]tetrahydrofuran-2-carboxamide (tetrahydrofuranylfentanyl; THF-F)". September 2017.

[2] Kanamori T, Segawa H, Yamamuro T, Kuwayama K, Tsujikawa K, Iwata YT (April 2020). "Metabolism of a new synthetic opioid tetrahydrofuranylfentanyl in fresh isolated human hepatocytes: Detection and confirmation of ring-opened metabolites". Drug Testing and Analysis. 12 (4): 439–448. doi:10.1002/dta.2743. PMID 31797567. S2CID 208627099.

[pmid25976511-3] 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.

[pmid29042317-4] Armenian P, Vo KT, Barr-Walker J, Lynch KL (May 2018). "Fentanyl, fentanyl analogs and novel synthetic opioids: A comprehensive review". Neuropharmacology. 134 (Pt A): 121–132. doi:10.1016/j.neuropharm.2017.10.016. PMID 29042317. S2CID 21404877.

[pmid29091366-5] Drug Enforcement Administration, Department of Justice (October 2017). "Schedules of Controlled Substances: Temporary Placement of ortho-Fluorofentanyl, Tetrahydrofuranyl Fentanyl, and Methoxyacetyl Fentanyl Into Schedule I. Temporary amendment; temporary scheduling order". Federal Register. 82 (206): 49504–49508. PMID 29091366.

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Side effects

Legal status

See also

References