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The structure-activity relationship of the drug class has been explored to a reasonable extent. The optimal substitution pattern is fairly tightly defined (i.e. N,N-diethyl on the amine nitrogen, 4-ethoxy on the benzyl ring and 5-nitro on the benzimidazole ring), but even derivatives incorporating only some of these features are still potent opioids.
Isotonitazene is a benzimidazole-derived opioid analgesic drug related to etonitazene, [3] [4] [5] which has been sold as a designer drug. [6] [7] [8] It has only ...
A 2011 publication [13] [J. Org. Chem., 2011, 76(23), 9577-9583] from a South Korean team outlined a novel, one-pot synthesis for substituted and unsubstituted 2-benzyl-benzimidazoles that can be easily adapted to the preparation of etonitazene.
Benzimidazole is a base: C 6 H 4 N(NH)CH + H + → [C 6 H 4 (NH) 2 CH] + It can also be deprotonated with stronger bases: C 6 H 4 N(NH)CH + LiH → Li [C 6 H 4 N 2 CH] + H 2. The imine can be alkylated and also serves as a ligand in coordination chemistry. The most prominent benzimidazole complex features N-ribosyl-dimethylbenzimidazole, as ...
Methylenedioxynitazene (3',4'-Methylenedioxynitazene) is a benzimidazole derivative which has been sold as a designer drug over the internet and presumably has opioid effects. It is an analogue of etonitazene where the benzyl ring is substituted with a 3,4-methylenedioxy ring system rather than an ethoxy group. It was first reported in the UK ...
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.
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]
Butonitazene is a benzimidazole derivative with opioid effects, which has been sold over the internet as a designer drug.It has relatively low potency compared to many related compounds, and has generally been encountered as a component of mixtures with other substances rather than in its pure form.