List of benzimidazole opioids
A number of benzimidazole opioids have been developed , the most famous of which is the highly effective, but never commercially available, etonitazene . The structure-activity relationship has been investigated to a reasonable extent. The optimal substitution pattern is quite clearly defined (for example, N, N-diethyl on amine nitrogen, 4-ethoxy on the benzyl ring and 5-nitro on the benzimidazole ring), but even derivatives that include only some of these properties are still potent opioids. . If a methyl or carboxamide group is added to the alpha carbon of the benzyl group or benzyl is replaced with 2-phenylethyl, compounds with similar activity are obtained. The values of relative analgesic activity are derived from tests on mice and cannot be extrapolated directly to humans, although general activity trends are applicable.
Publication showed the possibility that the previously assumed binding position of the benzimidazole class acting as a semi-rigid analogue of fentanyl may be incorrect. Based on a large-scale analysis of known ligands of opioid receptors using manual overlay and alignment, a matrix was created that identified several mu-specific regions within the receptor. In this analysis, it is noted that etonitazene now more closely corresponds to another separate mu-specific region having only a small total area with the fentanyl class.
Table of benzimidazole opioids
1-diethylaminoethyl-2-benzyl-benzimidazole hydrogen 0.1 28787
Metazene 4-methoxy 1 26412 14030-77-4
1071546-40-1 (HCl)
Ethodesnitazene (Etazene) 4-ethoxy 70 149797386
Etodesnitazene analog of pyrrolidine 4-ethoxy 20
Etodesnitazene analogue of piperidine 4-ethoxy 10
Protodesnitazene 4-(n-propoxy) 10
Isotodesnitazene 4-isopropoxy ~ 75
Nitazin hydrogen 2 15327524
metonitazene 3-methoxy 2
Metonitazene 4-methoxy 100 53316366 14680-51-4
Dimetonitazene 3,4-dimethoxy 10
α-methyl-methonitazene 4-methoxy 50
Metonitazene phenethyl homologue 4-methoxy 50
Aethonitazene 4-ethoxy 1000 13493 911-65-9
O-desmethyl-ethonitazene 4- hydroxy 1 94758-81-3
Etonitazene 5-amino metabolite 4-ethoxy 2 13408927
Etonitazene N, N-dimethyl analog 4-ethoxy 20
Ethonitazepine 4-ethoxy
Ethonitazene analogue of piperidine 4-ethoxy 100
Ethonitazene analogue of morpholine 4-ethoxy 2
Ethonitazene 6-nitroisomer 4-ethoxy 20
Protonitazene 4- (n-propoxy) 200 119276-01-6
Isotonitazene 4-isopropoxy 500 145721979 14188-81-9
N-dezethylisotonitazene 4-isopropoxy ~ 1000
Butonitazene 4-butoxy 5 95810-54-1
Etoethonitazene 4-ethoxyethoxy 50
Fluonitazene 4-fluoro 1 2728-91-8
Clonitazene 4- chlorine 3 62528 3861-76-5
α-carboxamido-clonitazene 4-chloro 3
Bronitazene 4-bromine 5
Methylnitazene 4-methyl 10
Ethylnitazene 4-ethyl 20
Propylnitazene 4-propyl 50
t-butylnitazene 4- (tert-butyl) 2
Acetoxynitazene 4-acetoxy 5
Methylthionitazene 4-methylthio 50
Ethylthionitazene 4-ethylthio 30
Ethodesnitazene analog of phenylthiol 4-ethoxy 1 21045
Etodesnitazene phenylthiol / pyrrolidine analogue 4-ethoxy 2 19846499