Piperidylthiambutene

Piperidylthiambutene (Piperidinohton) is a synthetic^[1] opioid analgesic drug from the thiambutene family, which has around the same potency as morphine.^[2][3][4] Piperidylthiambutene is structurally distinct from fentanyl, its analogues, and other synthetic opioids previously reported.^[1] If sold or obtained for the purpose of human consumption it could be considered a controlled substance analogue in some countries such as the US, Australia and New Zealand. Piperidylthiambutene has been sold as a designer drug, first appearing in late 2018.^[5][6]

Piperidylthiambutene

Clinical data
ATC code	none
Identifiers
IUPAC name 1-[4,4-Di(thiophen-2-yl)but-3-en-2-yl]piperidine
CAS Number	54160-31-5 Y
PubChem CID	3041503
ChemSpider	2304772
UNII	4BU0BCP2E1
CompTox Dashboard (EPA)	DTXSID50903299
Chemical and physical data
Formula	C17H21NS2
Molar mass	303.48 g·mol−1
3D model (JSmol)	Interactive image
Melting point	188 to 189 °C (370 to 372 °F)
SMILES C1CCCCN1C(C)C=C(c3cccs3)c2sccc2
InChI InChI=1S/C17H21NS2/c1-14(18-9-3-2-4-10-18)13-15(16-7-5-11-19-16)17-8-6-12-20-17/h5-8,11-14H,2-4,9-10H2,1H3 Key:FQRWJLVMJCKSME-UHFFFAOYSA-N
(verify)

Synthesis

Patent:^[7]

The Grignard reaction between 3-Piperidinobutyric acid ethyl ester, CID:10774378 (1) and 2-Bromothiophene [1003-09-4] (2) gives 3. Dehydration in acid completes the synthesis.