Β-Hydroxythiofentanyl

β-Hydroxythiofentanyl (beta-hydroxythiofentanyl) is an opioid analgesic that is an analog of fentanyl and thiofentanyl.

β-Hydroxythiofentanyl

Clinical data
ATC code	none
Legal status
Legal status	CA: Schedule I UK: Class A US: Schedule I
Identifiers
IUPAC name N-{1-[2-Hydroxy-2-(thiophen-2-yl)ethyl]piperidin-4-yl}-N-phenylpropanamide
CAS Number	1474-34-6
PubChem CID	62278
ChemSpider	21106268 Y
UNII	MG6JW60TUG
CompTox Dashboard (EPA)	DTXSID101014172
Chemical and physical data
Formula	C20H26N2O2S
Molar mass	358.50 g·mol−1
3D model (JSmol)	Interactive image
SMILES CCC(=O)N(c1ccccc1)C2CCN(CC2)CC(c3cccs3)O
InChI InChI=1S/C20H26N2O2S/c1-2-20(24)22(16-7-4-3-5-8-16)17-10-12-21(13-11-17)15-18(23)19-9-6-14-25-19/h3-9,14,17-18,23H,2,10-13,15H2,1H3 Y Key:GLAAETOTOUGGSB-UHFFFAOYSA-N Y
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β-Hydroxythiofentanyl was sold briefly on the black market from around 1985,^[1] before the introduction of the Federal Analog Act in 1986 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.^[2] β-hydroxythiofentanyl was anecdotally said to be one of the more favored fentanyl analogs by opiate addicts^{[citation needed]}.

Side Effects

β-Hydroxythiofentanyl has effects and side effects similar to fentanyl. Side effects of fentanyl analogs include itching, nausea and potentially serious respiratory depression, which can be life-threatening.^{[citation needed]}

Legal status

As of October 2015, β-hydroxythiofentanyl is a controlled substance in China.^[3]

As of May 2016, β-hydroxythiofentanyl was temporarily listed as a Schedule I controlled substance in the United States.^[4] A final ruling placing it in Schedule I was issued by the DEA on May 8, 2019 after a 1 year notice of proposed permanent scheduling.^[5] There were no petitions for hearings on the matter.^[6][7]

See also

• Sufentanil
• Thiafentanil

References

1. Valter K, Arrizabalaga P. Designer Drugs Directory (1998), p150. ISBN 0-444-20525-X
2. Henderson GL (1988). "Designer Drugs: Past History and Future Prospects". Journal of Forensic Sciences. 33 (2): 569–575. doi:10.1520/JFS11976J. PMID 3286815.
3. "关于印发《非药用类麻醉药品和精神药品列管办法》的通知" (in Chinese). China Food and Drug Administration. 27 September 2015. Archived from the original on 1 October 2015. Retrieved 1 October 2015.
4. "Schedules of Controlled Substances: Temporary Placement of Butyryl Fentanyl and Beta-Hydroxythiofentanyl into Schedule I" (PDF). Drug Enforcement Administration. 12 May 2016.
5. 5 U.S.C. § 556-557
6. Drug Enforcement Administration (May 8, 2019). "Schedules of Controlled Substances: Placement of beta-Hydroxythiofentanyl in Schedule I". Federal Register. 84 (89). Department of Justice: 20023–20027. Docket No. DEA–484. Retrieved 7 March 2024.
7. 21 CFR 1308.11