Piperidylthiambutene Explained

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. 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]}

Synthesis

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.

Notes and References

1. Web site: Piperidylthiambutene. 2020-09-14. NMS Labs.
2. Adamson DW, Green AF . A new series of analgesics . Nature . 165 . 4186 . 122 . January 1950 . 15409854 . 10.1038/165122a0 . 1950Natur.165..122A . 4190157 . free .
3. Adamson DW, Duffin WM, Green AF . Dithienylbutylamines as analgesics . Nature . 167 . 4239 . 153–4 . January 1951 . 14806409 . 10.1038/167153b0 . 1951Natur.167..153A . 4280042 .
4. Green AF . Analgesic and other properties of 3: 3-dithienylalkenylamines . British Journal of Pharmacology and Chemotherapy . 8 . 1 . 2–9 . March 1953 . 13066683 . 1509239 . 10.1111/j.1476-5381.1953.tb00739.x .
5. Web site: Analytical report Piperidylthiambutene. . European Project Response . November 2018 .
6. Vandeputte MM, Cannaert A, Stove CP . In vitro functional characterization of a panel of non-fentanyl opioid new psychoactive substances . Archives of Toxicology . 94 . 11 . 3819–3830 . November 2020 . 32734307 . 10.1007/s00204-020-02855-7 . 1854/LU-8687070 . 220881657 . free .