List of benzimidazole opioids

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Benzimidazole opioids, also known as nitazenes, are a class of synthetic opioids with an unusual benzimidazole structure; These chemicals are often called opioid NPS (or opioid New Psychoactive Substances).[1]

The best known of these opioids is etonitazene. Benzimidazole opioids bind the mu-opioid receptor and may show potency up to several hundred times that of morphine.

These opioids have been used in research,[2] and also are being used for drug abuse.[3][4][5] Isotonitazine has been implicated in opioid overdose deaths in Europe, Canada, and the United States beginning in 2019.[6] [5]

List of benzimidazole opioids

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Drug name Ring substitution Potency in
comparison
to
morphine
More info Chemical structure
Etonitazepyne 4-ethoxy  
Etonitazepipne[7] 4-ethoxy 190  
Etonitazene morpholine analogue 4-ethox  
Protonitazene  
Protonitazepyne 4-(n-propoxy) Pubchem  
Isotonitazene 4-isopropoxy Pubchem  
Isotonitazepyne 4-isopropoxy Pubchem  
N-Desethylisotonitazene 4-isopropoxy ~1000 times stronger Pubchem  
Butonitazene 4-butoxy 5 Pubchem  
Etoetonitazene 4-ethoxyethoxy 50 Pubchem  
Flunitazene 4-fluoro As potent
as morphine
Pubchem  
Clonitazene 4-chloro 3 Pubchem  

Sources

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  1. Ujváry I, Christie R, Evans-Brown M, Gallegos A, Jorge R, de Morais J, Sedefov R (April 2021). "DARK Classics in Chemical Neuroscience: Etonitazene and Related Benzimidazoles". ACS Chemical Neuroscience. 12 (7): 1072–1092. doi:10.1021/acschemneuro.1c00037. PMID 33760580. S2CID 232356192.
  2. Montanari E, Madeo G, Pichini S, Busardò FP, Carlier J (August 2022). "Acute Intoxications and Fatalities Associated With Benzimidazole Opioid (Nitazene Analog) Use: A Systematic Review". Therapeutic Drug Monitoring. 44 (4): 494–510. doi:10.1097/FTD.0000000000000970. PMID 35149665. S2CID 246776288.
  3. US patent 2935514, Karl Hoffman & Alfred Hunger, "BENZMDAZOLES", published 1960-05-03, assigned to Ciba Pharmaceutical Products Inc. 
  4. Drug Enforcement Administration (June 2021). "Benzimidazole Opioids" (PDF). Retrieved 6 January 2022.
  5. 5.0 5.1 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.
  6. European Monitoring Centre for Drugs Drug Addiction (2020-11-13). "Report on the risk assessment of N,N-diethyl-2- 4-(1-methylethoxy)phenyl]methyl]-5-nitro-1Hbenzimidazole- 1-ethanamine (isotonitazene) in accordance with Article 5c of Regulation (EC) No 1920/2006 (as amended)". European Monitoring Centre for Drugs and Drug Addiction. Publications Office of the European Union. doi:10.2810/107576. ISBN 9789294974952. Retrieved 9 May 2022.
  7. Vandeputte MM, Verougstraete N, Walther D, Glatfelter GC, Malfliet J, Baumann MH, Verstraete AG, Stove CP. First identification, chemical analysis and pharmacological characterization of N-piperidinyl etonitazene (etonitazepipne), a recent addition to the 2-benzylbenzimidazole opioid subclass. Arch Toxicol. 2022 Jun;96(6):1865-1880. doi:10.1007/s00204-022-03294-2 PubMed
  8. https://www.vg.no/nyheter/i/15Ao9e/tolletaten-om-doedsdopet-skremmende-utvikling. VG.no. Retrieved 2023-11-05
  9. Chimica Therapeutica 2(16): 1967.
  10. A review of the evidence on the use and harms of 2-benzyl benzimidazole (‘nitazene’) and piperidine benzimidazolone (‘brorphine-like’) opioids. Advisory Council on the Misuse of Drugs, UK. July 2022