etodesnitazene

{{Short description|Chemical compound}}

{{cs1 config|name-list-style=vanc}}

{{Drugbox

| drug_name = Desnitroetonitazene

| type =

| IUPAC_name = 2-[2-[(4-Ethoxyphenyl)methyl]benzimidazol-1-yl]-N,N-diethylethanamine

| image = Etodesnitazene.svg

| image_class = skin-invert-image

| width = 200

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| licence_US =

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| legal_BR = F1

| legal_DE = Anlage II

| legal_UK = PSA

| legal_US = Schedule I

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| CAS_number_Ref = {{cascite|correct|CAS}}

| CAS_number = 14030-76-3

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = H7YW5L26CS

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| PubChem = 149797386

| KEGG = C22827

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| ChEBI = 234368

| C = 22

| H = 29

| N = 3

| O = 1

| melting_point =

| smiles = CCN(CC)CCN1C2=CC=CC=C2N=C1CC3=CC=C(C=C3)OCC

| StdInChI = 1S/C22H29N3O/c1-4-24(5-2)15-16-25-21-10-8-7-9-20(21)23-22(25)17-18-11-13-19(14-12-18)26-6-3/h7-14H,4-6,15-17H2,1-3H3

| StdInChIKey = BMLPNUNXHUGDOI-UHFFFAOYSA-N

}}

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.{{cite journal | vauthors = Ujváry I, Christie R, Evans-Brown M, Gallegos A, Jorge R, de Morais J, Sedefov R | title = DARK Classics in Chemical Neuroscience: Etonitazene and Related Benzimidazoles | journal = ACS Chemical Neuroscience | volume = 12 | issue = 7 | pages = 1072–1092 | date = April 2021 | pmid = 33760580 | doi = 10.1021/acschemneuro.1c00037 | s2cid = 232356192 }} It is many times less potent than etonitazene itself, but still 70 times more potent than morphine in animal studies. Corresponding analogues where the N,N-diethyl group is replaced by piperidine or pyrrolidine rings also retain significant activity (10 times and 20 times morphine, respectively).{{cite journal | vauthors = Hunger A, Kebrle J, Rossi A, Hoffmann K | title = Benzimidazol-Derivate und verwandte Heterocyclen. II. Synthese von 1-Aminoalkyl-2-benzyl-benzimidazolen. | language = German | journal = Helvetica Chimica Acta | date = 1960 | volume = 43 | issue = 3 | pages = 800–809 | doi = 10.1002/hlca.19600430323 }} Etodesnitazene has been sold as a designer drug,{{cite journal| vauthors = Siczek M, Zawadzki M, Siczek M, Chłopaś-Konowałek A, Szpot P|title=Etazene (N,N-diethyl-2-{[(4-ethoxyphenyl)methyl]-1H-benzimidazol-1-yl}-ethan-1-amine (dihydrochloride)): a novel benzimidazole opioid NPS identified in seized material: crystal structure and spectroscopic characterization|journal=Forensic Toxicology|date=2020|issn=1860-8973|doi=10.1007/s11419-020-00552-9 |doi-access=free}} first being identified in both Poland and Finland in March 2020.{{Cite journal | vauthors = Siczek M, Zawadzki M, Siczek M, Chłopaś-Konowałek A, Szpot P |date=January 2021 |title=Etazene (N,N-diethyl-2-{[(4-ethoxyphenyl)methyl]-1H-benzimidazol-1-yl}-ethan-1-amine (dihydrochloride)): a novel benzimidazole opioid NPS identified in seized material: crystal structure and spectroscopic characterization |journal=Forensic Toxicology |language=en |volume=39 |issue=1 |pages=146–155 |doi=10.1007/s11419-020-00552-9 |issn=1860-8965|doi-access=free }}{{cite web | url = https://www.aekwien.at/documents/263869/449604/200629_EU+EARLY+WARNING+SYSTEM+SITUATION+REPORT+June.pdf | title = EU Early Warning System Situation Report. Situation report 1 | date = June 2020 | work = European Monitoring Centre for Drugs and Drug Addiction (EMCDDA) }}