Etonitazepipne

{{Short description|Benzimidazole derivative}}

{{cs1 config|name-list-style=vanc|display-authors=6}}

{{infobox drug

| drug_name = Etonitazepipne

| image = Etonitazepipne.svg

| legal_UK = PSA

| legal_DE = NpSG

| C = 23 | H = 28 | N = 4 | O = 3

| IUPAC_name = 2-[(4-Ethoxyphenyl)methyl]-5-nitro-1-(2-piperidin-1-ylethyl)benzimidazole

| CAS_number = 734496-28-7

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

| UNII = 7AF6EZ8PMY

| ChemSpiderID =

| PubChem = 162623834

| smiles = CCOC1=CC=C(C=C1)CC2=NC3=C(N2CCN4CCCCC4)C=CC(=C3)[N+](=O)[O-]

| StdInChI= 1S/C23H28N4O3/c1-2-30-20-9-6-18(7-10-20)16-23-24-21-17-19(27(28)29)8-11-22(21)26(23)15-14-25-12-4-3-5-13-25/h6-11,17H,2-5,12-16H2,1H3

| StdInChIKey = UMGXRAISFRUVKD-UHFFFAOYSA-N

}}

Etonitazepipne (N-piperidino etonitazene) is a benzimidazole derivative with opioid effects around 100 times more potent than morphine,{{cite journal | vauthors = Hunger A, Kebrle J, Rossi A, Hoffmann K | title = Benzimidazol-Derivate und verwandte Heterocyclen III. Synthese von 1-Aminoalkyl-2-benzyl-nitro-benzimidazolen. | journal = Helvetica Chimica Acta | date = 1960 | volume = 43 | issue = 4 | pages = 1032–1046 | doi = 10.1002/hlca.19600430412 }}{{cite journal | vauthors = Berardinelli D, Taoussi O, Carlier J, Tini A, Zaami S, Sundermann T, Busardò FP, Auwärter V | title = In vitro, in vivo metabolism and quantification of the novel synthetic opioid N-piperidinyl etonitazene (etonitazepipne) | journal = Clinical Chemistry and Laboratory Medicine | volume = 62 | issue = 8 | pages = 1580–1590 | date = July 2024 | pmid = 38311816 | doi = 10.1515/cclm-2023-1360 }} which has been sold over the internet as a designer drug.{{cite journal | title = Alert from NDEWS Web Monitoring Team: Increase in discussion of etonitazepipne | url = https://ndews.org/?wysija-page=1&controller=email&action=view&email_id=168&wysijap=subscriptions | journal = National Drug Early Warning System. Weekly Briefing | issue = 43 | date = 9 July 2021 }}{{cite web | url = https://knowdrugs.app/drugs/Vm3RqXhdeiyRUXx7oRwW/Etonitazepipne | title = Warnings Etonitazepipne | work = Knowdrugs.app | date = 9 August 2021 }}{{cite journal | vauthors = Vandeputte MM, Verougstraete N, Walther D, Glatfelter GC, Malfliet J, Baumann MH, Verstraete AG, Stove CP | title = First identification, chemical analysis and pharmacological characterization of N-piperidinyl etonitazene (etonitazepipne), a recent addition to the 2-benzylbenzimidazole opioid subclass | journal = Archives of Toxicology | volume = 96 | issue = 6 | pages = 1865–1880 | date = June 2022 | pmid = 35449307 | doi = 10.1007/s00204-022-03294-2 | s2cid = 253718213 | hdl = 1854/LU-8751259 | hdl-access = free }}{{cite journal | vauthors = Calello DP, Aldy K, Jefri M, Nguyen TT, Krotulski A, Logan B, Brent J, Wax P, Walton S, Manini AF | title = Identification of a novel opioid, N-piperidinyl etonitazene (etonitazepipne), in patients with suspected opioid overdose | journal = Clinical Toxicology | volume = 60 | issue = 9 | pages = 1067–1069 | date = September 2022 | pmid = 35708103 | pmc = 9815205 | doi = 10.1080/15563650.2022.2084406 }}