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
change- Nitazene; Ring substitution, hydrogen. The chemical structure can be drawn, as follows,
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 |
- Metodesnitazene (Metazene); Ring substitution, 4-methoxy; Structural formula,
- Etodesnitazene (Etazene); 4-ethoxy.
- Etonitazene, 4-ethoxy.
- N-Desethyletonitazene (NDE); 4-ethoxy.
- Etomethazene, 4-ethoxy.
- Etonitazene 5-cyano analogue (Etocyanazene).[9] 4-ethoxy,
- Etonitazene 5-acetyl analogue (Etoacetazene).[10] 4-ethoxy;
Sources
change- ↑ 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.
- ↑ 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.
- ↑ US patent 2935514, Karl Hoffman & Alfred Hunger, "BENZMDAZOLES", published 1960-05-03, assigned to Ciba Pharmaceutical Products Inc.
- ↑ Drug Enforcement Administration (June 2021). "Benzimidazole Opioids" (PDF). Retrieved 6 January 2022.
- ↑ 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.
- ↑ 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.
- ↑ 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
- ↑ https://www.vg.no/nyheter/i/15Ao9e/tolletaten-om-doedsdopet-skremmende-utvikling. VG.no. Retrieved 2023-11-05
- ↑ Chimica Therapeutica 2(16): 1967.
- ↑ 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