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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.
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.
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 ...
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 ...
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 ...
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.
2-(Ethylamino)-1,2-diphenylethanone (also known as α-ethylamino-deoxybenzoin, [α-(Ethylamino)benzyl]-(phenyl)-ketone and βk-Ephenidine) is a chemical compound which was first invented in 1955, [1] researched by ICI in 1969 as an antidepressant, [2] and subsequently claimed by AstraZeneca as an inhibitor of the enzyme 11β-Hydroxysteroid dehydrogenase type 1. [3]
Benznidazole is an antiparasitic medication used in the treatment of Chagas disease. [2] While it is highly effective in early disease, the effectiveness decreases in those who have long-term infection. [3] It is the first-line treatment given its moderate side effects compared to nifurtimox. [1] It is taken by mouth. [2] Side effects are ...