piperidylthiambutene

{{Short description|Chemical compound}}

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{{Drugbox

| verifiedrevid = 451982308

| IUPAC_name = 1-[4,4-Di(thiophen-2-yl)but-3-en-2-yl]piperidine

| image = Piperidylthiambutene Structure.svg

| image_class = skin-invert-image

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| routes_of_administration =

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| CAS_number_Ref = {{cascite|correct|??}}

| CAS_number = 54160-31-5

| ATC_prefix = none

| ATC_suffix =

| PubChem = 3041503

| ChemSpiderID = 2304772

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = 4BU0BCP2E1

| C=17 | H=21 | N=1 | S=2

| smiles = C1CCCCN1C(C)C=C(c3cccs3)c2sccc2

| StdInChI = 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

| StdInChIKey = FQRWJLVMJCKSME-UHFFFAOYSA-N

| melting_point = 188

| melting_high = 189

}}

Piperidylthiambutene (Piperidinohton) is a synthetic{{Cite web|date=|title=Piperidylthiambutene|url=https://www.npsdiscovery.org/wp-content/uploads/2019/09/Piperidylthiambutene_091819_NMSLabs_Report.pdf|archive-url=|archive-date=|access-date=2020-09-14|website=NMS Labs}} opioid analgesic drug from the thiambutene family, which has around the same potency as morphine.{{cite journal | vauthors = Adamson DW, Green AF | title = A new series of analgesics | journal = Nature | volume = 165 | issue = 4186 | pages = 122 | date = January 1950 | pmid = 15409854 | doi = 10.1038/165122a0 | bibcode = 1950Natur.165..122A | s2cid = 4190157 | doi-access = free }}{{cite journal | vauthors = Adamson DW, Duffin WM, Green AF | title = Dithienylbutylamines as analgesics | journal = Nature | volume = 167 | issue = 4239 | pages = 153–4 | date = January 1951 | pmid = 14806409 | doi = 10.1038/167153b0 | bibcode = 1951Natur.167..153A | s2cid = 4280042 }}{{cite journal | vauthors = Green AF | title = Analgesic and other properties of 3: 3-dithienylalkenylamines | journal = British Journal of Pharmacology and Chemotherapy | volume = 8 | issue = 1 | pages = 2–9 | date = March 1953 | pmid = 13066683 | pmc = 1509239 | doi = 10.1111/j.1476-5381.1953.tb00739.x }} 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.{{cite web | url = https://www.policija.si/apps/nfl_response_web/0_Analytical_Reports_final/Piperidylthiambutene-ID-2034-18_report.pdf | title = Analytical report Piperidylthiambutene. | work = European Project Response | date = November 2018 }}{{cite journal | vauthors = Vandeputte MM, Cannaert A, Stove CP | title = In vitro functional characterization of a panel of non-fentanyl opioid new psychoactive substances | journal = Archives of Toxicology | volume = 94 | issue = 11 | pages = 3819–3830 | date = November 2020 | pmid = 32734307 | doi = 10.1007/s00204-020-02855-7 | hdl = 1854/LU-8687070 | s2cid = 220881657 | url = https://biblio.ugent.be/publication/8687070 | hdl-access = free }}

Synthesis

File:Piperidylthiambutene synthesis.svg

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

References