List of benzimidazole opioids

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

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, and also are being used for drug abuse. Isotonitazine has been implicated in opioid overdose deaths in Europe, Canada, and the United States beginning in 2019.

List of benzimidazole opioids


Drug name Ring substitution Potency in
comparison
to
morphine
More info Chemical structure
Etonitazepyne 4-ethoxy
Etonitazepipne 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

  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, "BENZiMiDAZOLES", published 1960-05-03, assigned to Ciba Pharmaceutical Products Inc.
  4. ↑ Drug Enforcement Administration (June 2021). "Benzimidazole Opioids" (PDF). Retrieved 6 January 2022.
  5. 1 2 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.{{cite journal}}: CS1 maint: periodical has ISBN (link)
  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. ↑ (norsk) 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