3-Methylthiofentanyl

3-Methylthiofentanyl

Legal status
Legal status	CA: Schedule I DE: Anlage I (Controlled) UK: Class A US: Schedule I
Identifiers
IUPAC name (RS)-N-{3-methyl-1-[2-(2-thienyl)ethyl]piperidin-4-yl}-N-phenylpropanamide
Synonyms	N-[3-methyl-1-(2-thiophen-2-ylethyl)-4-piperidyl]-N-phenyl-propanamide; 3-methyl-thiofentanyl
CAS Number	86052-04-2
PubChem (CID)	62296
DrugBank	DB01439
ChemSpider	56092
ChEBI	CHEBI:53763
Chemical and physical data
Formula	C21H28N2OS
Molar mass	356.526 g/mol
3D model (Jmol)	Interactive image
SMILES O=C(N(c1ccccc1)C2CCN(CC2C)CCc3sccc3)CC
InChI InChI=1S/C21H28N2OS/c1-3-21(24)23(18-8-5-4-6-9-18)20-12-14-22(16-17(20)2)13-11-19-10-7-15-25-19/h4-10,15,17,20H,3,11-14,16H2,1-2H3 Key:SRARDYUHGVMEQI-UHFFFAOYSA-N
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3-Methyl-thiofentanyl is an opioid analgesic and analogue of fentanyl.

3-Methyl-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]

3-Methyl-thiofentanyl has similar effects to fentanyl. 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]

See also

• 3-Methylbutyrfentanyl
• 4-Fluorofentanyl
• 4-Methylfentanyl (also Serbian chemical society).^[3]
• α-Methylfentanyl
• Acetylfentanyl
• Butyrfentanyl
• List of Fentanyl analogues

References

1. Henderson, GL (1988). "Designer Drugs: Past History and Future Prospects". Journal of Forensic Sciences. 33 (2): 569–575.
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 of drug policy. 26 (7): 626–631. doi:10.1016/j.drugpo.2015.04.003. PMID 25976511.
3. Mićović, I. V.; Ivanović, M. D.; Vuckovic, S. M.; Prostran, M. Š.; Došen-Mićović, L.; Kiricojević, V. D. (2000). "The Synthesis and preliminary pharmacological evaluation of 4-Methyl fentanyl". Bioorganic & Medicinal Chemistry Letters. 10 (17): 2011–2014. doi:10.1016/S0960-894X(00)00394-2.