Thenylfentanyl

Thenylfentanyl
	Chemical structure of thenylfentanyl
Legal status
Legal status	US: Unscheduled;
Identifiers
	IUPAC name N-Phenyl-N-[1-(thiophen-2-ylmethyl)piperidin-4-yl]propanamide;
CAS Number	122861-39-6;
PubChem CID	21595404;
ChemSpider	10551387;
UNII	7O0847NUE9;
ChEMBL	ChEMBL2365725;
CompTox Dashboard (EPA)	DTXSID30861242 ;
Chemical and physical data
Formula	C19H24N2OS
Molar mass	328.47 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CCC(=O)N(C1CCN(CC1)CC2=CC=CS2)C3=CC=CC=C3;
	InChI InChI=InChI=1S/C19H24N2OS/c1-2-19(22)21(16-7-4-3-5-8-16)17-10-12-20(13-11-17)15-18-9-6-14-23-18/h3-9,14,17H,2,10-13,15H2,1H3; Key:JSOSWRYHPGIWGT-UHFFFAOYSA-N;

Thenylfentanyl is an analogue of fentanyl where the phenethylamine side-chain has been replaced by a thiophenylmethyl group. It was temporarily scheduled by the Drug Enforcement Administration in 1985,^[1] due to fears it would be used as a designer drug. But in 2010 the DEA acknowledged it was essentially inactive.^[2] Subsequently, the substance was since deregulated.

Legal status

The legality of fentanyl analogues vary by country. In the United States, thenylfentanyl is unscheduled.

Uses

In much the same way that benzylfentanyl can be used to synthesize fentanyl, thenylfentanyl could ostensibly be used for the same purpose. In such a procedure, thenylfentanyl would first be de-thiophenylmethylated to norfentanyl. This would be followed by amination to fentanyl using phenethyl bromide.^[3]

Chemistry

Thenylfentanyl is a N-arylalkylamide derivative of norfentanyl. The substance is also a structural isomer of acetylthiofentanyl, wherein a methyl group on the thiophene sidechain has been relocated to the carboxamide group nearest the aniline. It is due to this reduced sidechain length that Thenylfentanyl has dramatically diminished MOR activity compared to other fentanyl analogues. Many of fentanyl’s analogues were discovered by Paul Janssen.

References

^ "Schedules of Controlled Substances: Temporary Placement of Acetyl-alpha-methylfentanyl, Alpha-methylthiofentanyl, Benzylfentanyl, Beta-hydroxyfentanyl, Beta-hydroxy-3-methylfentanyl, 3-Methylthiofentanyl, Thenylfentanyl, and Thiofentanyl into Schedule I of the Controlled Substances Act" (PDF). Isomer Design. Drug Enforcement Administration. October 29, 1985. Archived (PDF) from the original on March 3, 2022. Retrieved January 16, 2023.
^ "Removal of Temporary Listing of Benzylfentanyl and Thenylfentanyl as Controlled Substances". Federal Register. Drug Enforcement Administration. June 29, 2010.
^ "Fentanyl Synthesis". GPTA India. June 18, 2020. Archived from the original on December 28, 2022.

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[1] "Schedules of Controlled Substances: Temporary Placement of Acetyl-alpha-methylfentanyl, Alpha-methylthiofentanyl, Benzylfentanyl, Beta-hydroxyfentanyl, Beta-hydroxy-3-methylfentanyl, 3-Methylthiofentanyl, Thenylfentanyl, and Thiofentanyl into Schedule I of the Controlled Substances Act" (PDF). Isomer Design. Drug Enforcement Administration. October 29, 1985. Archived (PDF) from the original on March 3, 2022. Retrieved January 16, 2023.

[2] "Removal of Temporary Listing of Benzylfentanyl and Thenylfentanyl as Controlled Substances". Federal Register. Drug Enforcement Administration. June 29, 2010.

[3] "Fentanyl Synthesis". GPTA India. June 18, 2020. Archived from the original on December 28, 2022.

[1]

[2]

[3]

Legal status

Uses

Chemistry

See also

References