Thenylfentanyl

Not to be confused with Thiafentanil or Thiofentanyl.

Thenylfentanyl is an analogue of fentanyl where the phenethylamine side-chain has been replaced by a thiophenylmethyl group.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.

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

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

Statue of Paul Janssen

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 Belgian physician Paul Janssen.

See also

• Homofentanyl
• Isofentanyl
• Benzylfentanyl