Thiofentanyl

Thiofentanyl is an opioid analgesic that is an analogue of fentanyl.

Not to be confused with Thiafentanil.

Thiofentanyl

Clinical data
Pregnancy category	C
ATC code	none
Legal status
Legal status	AU: S9 (Prohibited substance) CA: Schedule I DE: Anlage I (Authorized scientific use only) UK: Class A US: Schedule I
Identifiers
IUPAC name N-phenyl-N-{1-[2-(2-thienyl)ethyl]piperidin-4-yl}propanamide
CAS Number	1165-22-6^N
PubChem CID	62380
ChemSpider	56168^Y
UNII	954535Y32Y
ChEBI	CHEBI:61099^Y
CompTox Dashboard (EPA)	DTXSID00151400
Chemical and physical data
Formula	C20H26N2OS
Molar mass	342.50 g·mol^−1
3D model (JSmol)	Interactive image
SMILES O=C(CC)N(C1CCN(CCC2=CC=CS2)CC1)C3=CC=CC=C3
InChI InChI=1S/C20H26N2OS/c1-2-20(23)22(17-7-4-3-5-8-17)18-10-13-21(14-11-18)15-12-19-9-6-16-24-19/h3-9,16,18H,2,10-15H2,1H3^Y Key:YMRFZDHYDKZXPA-UHFFFAOYSA-N^Y
^NY (what is this?)  (verify)

Thiofentanyl was sold briefly on the black market in the early 1980s, before the introduction of the Federal Analog Act which for the first time attempted to control entire families of drugs based on their structural similarity rather than scheduling each drug individually as they appeared.[1] Thiofentanyl is made with the same synthetic route as fentanyl, but by substituting 2-(2-bromoethyl)thiophene for phenethyl bromide in the synthesis.

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.[2]

References

1. Henderson GL (March 1988). "Designer drugs: past history and future prospects". Journal of Forensic Sciences. 33 (2): 569–75. doi:10.1520/JFS11976J. PMID 3286815.
2. 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): 626–31. doi:10.1016/j.drugpo.2015.04.003. PMID 25976511.