Etonitazepipne

Etonitazepipne
Legal status
Legal status	DE: NpSG (Industrial and scientific use only); UK: Under Psychoactive Substances Act;
Identifiers
	IUPAC name 2-[(4-Ethoxyphenyl)methyl]-5-nitro-1-(2-piperidin-1-ylethyl)benzimidazole;
CAS Number	734496-28-7;
PubChem CID	162623834;
UNII	7AF6EZ8PMY;
CompTox Dashboard (EPA)	DTXSID401337650 ;
Chemical and physical data
Formula	C23H28N4O3
Molar mass	408.502 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CCOC1=CC=C(C=C1)CC2=NC3=C(N2CCN4CCCCC4)C=CC(=C3)[N+](=O)[O-];
	InChI InChI=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; Key:UMGXRAISFRUVKD-UHFFFAOYSA-N;

Etonitazepipne (N-piperidino etonitazene) is a benzimidazole derivative with opioid effects around 100 times more potent than morphine,^[1]^[2] which has been sold over the internet as a designer drug.^[3]^[4]^[5]^[6]

References

^ Hunger A, Kebrle J, Rossi A, Hoffmann K (1960). "Benzimidazol-Derivate und verwandte Heterocyclen III. Synthese von 1-Aminoalkyl-2-benzyl-nitro-benzimidazolen". Helvetica Chimica Acta. 43 (4): 1032–1046. doi:10.1002/hlca.19600430412.
^ Berardinelli D, Taoussi O, Carlier J, Tini A, Zaami S, Sundermann T, et al. (July 2024). "In vitro, in vivo metabolism and quantification of the novel synthetic opioid N-piperidinyl etonitazene (etonitazepipne)". Clinical Chemistry and Laboratory Medicine. 62 (8): 1580–1590. doi:10.1515/cclm-2023-1360. PMID 38311816.
^ "Alert from NDEWS Web Monitoring Team: Increase in discussion of etonitazepipne". National Drug Early Warning System. Weekly Briefing (43). 9 July 2021.
^ "Warnings Etonitazepipne". Knowdrugs.app. 9 August 2021.
^ Vandeputte MM, Verougstraete N, Walther D, Glatfelter GC, Malfliet J, Baumann MH, et al. (June 2022). "First identification, chemical analysis and pharmacological characterization of N-piperidinyl etonitazene (etonitazepipne), a recent addition to the 2-benzylbenzimidazole opioid subclass". Archives of Toxicology. 96 (6): 1865–1880. doi:10.1007/s00204-022-03294-2. hdl:1854/LU-8751259. PMID 35449307. S2CID 253718213.
^ Calello DP, Aldy K, Jefri M, Nguyen TT, Krotulski A, Logan B, et al. (September 2022). "Identification of a novel opioid, N-piperidinyl etonitazene (etonitazepipne), in patients with suspected opioid overdose". Clinical Toxicology. 60 (9): 1067–1069. doi:10.1080/15563650.2022.2084406. PMC 9815205. PMID 35708103.

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[1] Hunger A, Kebrle J, Rossi A, Hoffmann K (1960). "Benzimidazol-Derivate und verwandte Heterocyclen III. Synthese von 1-Aminoalkyl-2-benzyl-nitro-benzimidazolen". Helvetica Chimica Acta. 43 (4): 1032–1046. doi:10.1002/hlca.19600430412.

[Berardinelli_2024-2] Berardinelli D, Taoussi O, Carlier J, Tini A, Zaami S, Sundermann T, et al. (July 2024). "In vitro, in vivo metabolism and quantification of the novel synthetic opioid N-piperidinyl etonitazene (etonitazepipne)". Clinical Chemistry and Laboratory Medicine. 62 (8): 1580–1590. doi:10.1515/cclm-2023-1360. PMID 38311816.

[3] "Alert from NDEWS Web Monitoring Team: Increase in discussion of etonitazepipne". National Drug Early Warning System. Weekly Briefing (43). 9 July 2021.

[4] "Warnings Etonitazepipne". Knowdrugs.app. 9 August 2021.

[5] Vandeputte MM, Verougstraete N, Walther D, Glatfelter GC, Malfliet J, Baumann MH, et al. (June 2022). "First identification, chemical analysis and pharmacological characterization of N-piperidinyl etonitazene (etonitazepipne), a recent addition to the 2-benzylbenzimidazole opioid subclass". Archives of Toxicology. 96 (6): 1865–1880. doi:10.1007/s00204-022-03294-2. hdl:1854/LU-8751259. PMID 35449307. S2CID 253718213.

[6] Calello DP, Aldy K, Jefri M, Nguyen TT, Krotulski A, Logan B, et al. (September 2022). "Identification of a novel opioid, N-piperidinyl etonitazene (etonitazepipne), in patients with suspected opioid overdose". Clinical Toxicology. 60 (9): 1067–1069. doi:10.1080/15563650.2022.2084406. PMC 9815205. PMID 35708103.

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See also

References