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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.
Etodesnitazene (also known as desnitroetonitazene, etazen, etazene, and etazone) is a benzimidazole-derived opioid analgesic drug, which was originally developed in the late 1950s alongside etonitazene and a range of related derivatives. [1]
The three component synthesis of the direct etonitazene precursor, 2-(4-Ethoxybenzyl)-5-nitro-1H-benzoimidazole, consists of a 2-Bromo- or 2-Iodo-5-nitro-phenylamine (1.0 molar equivalent), a 4-substituted benzaldehyde (1.2 equiv), and sodium azide (2 equiv). The 2-Halo-5-nitro-phenylamine requires a bromo or iodo group for optimal activity.
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 ...
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 ...
Maximum pesticide residue limits (MRLs) for fresh produce in the EU are between 0.1 and 0.7 mg/kg with the exception of loquat fruits, which is set at 2 mg/kg. [8] The limits for more commonly consumed citrus and pome fruits are between 0.1 and 0.2 mg/kg. Use of this fungicide on macadamia plantations has proven controversial in Queensland. [4]
Divinylbenzene (DVB) is an organic compound with the chemical formula C 6 H 4 (CH=CH 2) 2 and structure H 2 C=CH−C 6 H 4 −HC=CH 2 (a benzene ring with two vinyl groups as substituents).It is related to styrene (vinylbenzene, C 6 H 5 −CH=CH 2) by the addition of a second vinyl group. [2]