Betahydroxythiofentanyl

Betahydroxythiofentanyl
Clinical data
Other names	β-hydroxythiofentanyl
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 ;
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 ; Key:GLAAETOTOUGGSB-UHFFFAOYSA-N ;
	(verify)

Betahydroxythiofentanyl (β-hydroxythiofentanyl) is an opioid analgesic that is an analogue of fentanyl.

Betahydroxythiofentanyl 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 analogues by opiate addicts, but nevertheless its brief career as a street drug did not survive the introduction of the Analogues Act.

Betahydroxythiofentanyl 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.^[3]

Legal status

As of October 2015, betahydroxythiofentanyl is a controlled substance in China.^[4]

As of May 2016, betahydroxythiofentanyl is a Schedule I controlled substance in the United States.^[5]

References

^ Valter K, Arrizabalaga P. Designer Drugs Directory (1998), p150. ISBN 0-444-20525-X
^ Henderson, GL (1988). "Designer Drugs: Past History and Future Prospects". Journal of Forensic Sciences. 33 (2): 569–575.
^ Jane Mounteney; Isabelle Giraudon; Gleb Denissov; Paul Griffiths (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.
^ "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. Retrieved 1 October 2015.
^ "Schedules of Controlled Substances: Temporary Placement of Butyryl Fentanyl and Beta-Hydroxythiofentanyl into Schedule I" (PDF). Drug Enforcement Administration. 12 May 2016.

[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.

[3] Jane Mounteney; Isabelle Giraudon; Gleb Denissov; Paul Griffiths (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.

[4] "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. Retrieved 1 October 2015.

[5] "Schedules of Controlled Substances: Temporary Placement of Butyryl Fentanyl and Beta-Hydroxythiofentanyl into Schedule I" (PDF). Drug Enforcement Administration. 12 May 2016.

[1]

[2]

[3]

[4]

[5]