Piperidylthiambutene

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 ;
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)

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

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

^ ^a ^b "Piperidylthiambutene" (PDF). NMS Labs. Retrieved 2020-09-14.
^ 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.
^ 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.
^ 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.
^ "Analytical report Piperidylthiambutene" (PDF). European Project Response. November 2018.
^ 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.
^ Adamson Donald Wallace, U.S. patent 2,561,899 (1951 to Burroughs Wellcome Co).

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[:0-1] "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.

[pmid32734307-6] 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).

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