Piperidylthiambutene
Clinical data
ATC code
  • none
Identifiers
  • 1-[4,4-Di(thiophen-2-yl)but-3-en-2-yl]piperidine
CAS Number
PubChem CID
ChemSpider
UNII
Chemical and physical data
FormulaC17H21NS2
Molar mass303.48 g·mol−1
3D model (JSmol)
Melting point188 to 189 °C (370 to 372 °F)
  • C1CCCCN1C(C)C=C(c3cccs3)c2sccc2
  • 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)

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]

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.

References

  1. ^ a b "Piperidylthiambutene" (PDF). NMS Labs. Retrieved 2020-09-14.
  2. ^ Adamson DW, Green AF (January 1950). "A new series of analgesics". Nature. 165 (4186): 122. Bibcode:1950Natur.165..122A. doi:10.1038/165122a0. PMID 15409854. S2CID 4190157.
  3. ^ Adamson DW, Duffin WM, Green AF (January 1951). "Dithienylbutylamines as analgesics". Nature. 167 (4239): 153–4. Bibcode:1951Natur.167..153A. doi:10.1038/167153b0. PMID 14806409. S2CID 4280042.
  4. ^ Green AF (March 1953). "Analgesic and other properties of 3: 3-dithienylalkenylamines". British Journal of Pharmacology and Chemotherapy. 8 (1): 2–9. doi:10.1111/j.1476-5381.1953.tb00739.x. PMC 1509239. PMID 13066683.
  5. ^ "Analytical report Piperidylthiambutene" (PDF). European Project Response. November 2018.
  6. ^ Vandeputte MM, Cannaert A, Stove CP (November 2020). "In vitro functional characterization of a panel of non-fentanyl opioid new psychoactive substances". Archives of Toxicology. 94 (11): 3819–3830. doi:10.1007/s00204-020-02855-7. hdl:1854/LU-8687070. PMID 32734307. S2CID 220881657.
  7. ^ Adamson Donald Wallace, U.S. patent 2,561,899 (1951 to Burroughs Wellcome Co).


Categories