N-Desethylisotonitazene

N-Desethylisotonitazene
Clinical data
Routes of; administration	Oral, intransal, vaporized
Legal status
Legal status	DE: Anlage II (Authorized trade only, not prescriptible); UK: Under Psychoactive Substances Act;
Identifiers
	IUPAC name N-ethyl-2-[5-nitro-2-[(4-propoxyphenyl)methyl]benzimidazol-1-yl]ethanamine;
CAS Number	2732926-24-6;
PubChem CID	162623899;
UNII	T7LMM4S8UR;
Chemical and physical data
Formula	C21H26N4O3
Molar mass	382.464 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CCNCCN1C2=C(C=C(C=C2)[N+](=O)[O-])N=C1CC3=CC=C(C=C3)OC(C)C;
	InChI InChI=1S/C21H26N4O3/c1-4-22-11-12-24-20-10-7-17(25(26)27)14-19(20)23-21(24)13-16-5-8-18(9-6-16)28-15(2)3/h5-10,14-15,22H,4,11-13H2,1-3H3; Key:HHBRZWRJZICFRP-UHFFFAOYSA-N;

N-Desethylisotonitazene (norisotonitazene) is a benzimidazole opioid with potent analgesic effects which has been sold as a designer drug. It was first identified in 2023 as an active metabolite of the closely related compound isotonitazene, and was found to have similar potency. It is one of the strongest benzimidazole opioids discovered, with an analgesic strength 20 times stronger than fentanyl.

Starting in 2023, it has become an increasingly widespread drug of abuse in its own right, linked to numerous overdose cases, and may be considered an analog of the schedule 1 drug metonitazene. In October 2023, the DEA published an intent to temporarily schedule etonitazepipne and N-desethylisotonitazene. As of April 2024, it is not yet controlled in the United States.^[1]^[2]^[3]^[4]^[5]^[6]^[7]

References

^ Krotulski AJ, Papsun DM, Kacinko SL, Logan BK (July 2020). "Isotonitazene Quantitation and Metabolite Discovery in Authentic Forensic Casework". Journal of Analytical Toxicology. 44 (6): 521–530. doi:10.1093/jat/bkaa016. PMID 32091095.
^ Vandeputte MM, Van Uytfanghe K, Layle NK, St Germaine DM, Iula DM, Stove CP (April 2021). "Synthesis, Chemical Characterization, and μ-Opioid Receptor Activity Assessment of the Emerging Group of "Nitazene" 2-Benzylbenzimidazole Synthetic Opioids". ACS Chemical Neuroscience. 12 (7): 1241–1251. doi:10.1021/acschemneuro.1c00064. hdl:1854/LU-8714061. PMID 33759494. S2CID 232337929.
^ Walton SE, Krotulski AJ, Logan BK (March 2022). "A Forward-Thinking Approach to Addressing the New Synthetic Opioid 2-Benzylbenzimidazole Nitazene Analogs by Liquid Chromatography-Tandem Quadrupole Mass Spectrometry (LC-QQQ-MS)". Journal of Analytical Toxicology. 46 (3): 221–231. doi:10.1093/jat/bkab117. PMC 8935987. PMID 34792157.
^ Vandeputte MM, Tsai MM, Chen L, Glatfelter GC, Walther D, Stove CP, et al. (May 2023). "Comparative neuropharmacology of structurally distinct non-fentanyl opioids that are appearing on recreational drug markets worldwide". Drug and Alcohol Dependence. 249: 109939. doi:10.1016/j.drugalcdep.2023.109939. PMC 10330921. PMID 37276825. S2CID 258880063.
^ Malcolm NJ, Palkovic B, Sprague DJ, Calkins MM, Lanham JK, Halberstadt AL, Stucke AG, McCorvy JD. Mu-opioid Receptor Selective Superagonists Produce Prolonged Respiratory Depression. ISCIENCE (2023) doi:10.1016/j.isci.2023.107121
^ Taylor M (30 January 2023). "Opioid 20x More Potent than Fentanyl Detected in Pennsylvania, Florida". Forensic.
^ "Federal Register :: Request Access". 25 October 2023.

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[1] Krotulski AJ, Papsun DM, Kacinko SL, Logan BK (July 2020). "Isotonitazene Quantitation and Metabolite Discovery in Authentic Forensic Casework". Journal of Analytical Toxicology. 44 (6): 521–530. doi:10.1093/jat/bkaa016. PMID 32091095.

[2] Vandeputte MM, Van Uytfanghe K, Layle NK, St Germaine DM, Iula DM, Stove CP (April 2021). "Synthesis, Chemical Characterization, and μ-Opioid Receptor Activity Assessment of the Emerging Group of "Nitazene" 2-Benzylbenzimidazole Synthetic Opioids". ACS Chemical Neuroscience. 12 (7): 1241–1251. doi:10.1021/acschemneuro.1c00064. hdl:1854/LU-8714061. PMID 33759494. S2CID 232337929.

[3] Walton SE, Krotulski AJ, Logan BK (March 2022). "A Forward-Thinking Approach to Addressing the New Synthetic Opioid 2-Benzylbenzimidazole Nitazene Analogs by Liquid Chromatography-Tandem Quadrupole Mass Spectrometry (LC-QQQ-MS)". Journal of Analytical Toxicology. 46 (3): 221–231. doi:10.1093/jat/bkab117. PMC 8935987. PMID 34792157.

[4] Vandeputte MM, Tsai MM, Chen L, Glatfelter GC, Walther D, Stove CP, et al. (May 2023). "Comparative neuropharmacology of structurally distinct non-fentanyl opioids that are appearing on recreational drug markets worldwide". Drug and Alcohol Dependence. 249: 109939. doi:10.1016/j.drugalcdep.2023.109939. PMC 10330921. PMID 37276825. S2CID 258880063.

[5] Malcolm NJ, Palkovic B, Sprague DJ, Calkins MM, Lanham JK, Halberstadt AL, Stucke AG, McCorvy JD. Mu-opioid Receptor Selective Superagonists Produce Prolonged Respiratory Depression. ISCIENCE (2023) doi:10.1016/j.isci.2023.107121

[6] Taylor M (30 January 2023). "Opioid 20x More Potent than Fentanyl Detected in Pennsylvania, Florida". Forensic.

[7] "Federal Register :: Request Access". 25 October 2023.

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See also

References