Etonitazene 5-acetyl analogue

Chemical compound Pharmaceutical compound

Etoacetazene
Identifiers

IUPAC name 1--2-benzimidazol-5-yl]ethanone
CAS Number	13406-60-5
PubChem CID	25957
ChemSpider	24182
ChEMBL	ChEMBL4468889
CompTox Dashboard (EPA)	DTXSID10158480
Chemical and physical data
Formula	C₂₄H₃₁N₃O₂
Molar mass	393.531 g·mol
3D model (JSmol)	Interactive image
SMILES CCN(CC)CCN1C2=C(C=C(C=C2)C(=O)C)N=C1CC3=CC=C(C=C3)OCC
InChI InChI=1S/C24H31N3O2/c1-5-26(6-2)14-15-27-23-13-10-20(18(4)28)17-22(23)25-24(27)16-19-8-11-21(12-9-19)29-7-3/h8-13,17H,5-7,14-16H2,1-4H3 Key:CFGBPNSLTKLAKK-UHFFFAOYSA-N

Etonitazene 5-acetyl analogue (Etoacetazene, 5-acetyldesnitroetonitazene) is a benzimidazole derivative with opioid effects, first developed in the 1950s as part of the research that led to better-known compounds such as etonitazene. It is an analogue of etonitazene where the 5-nitro (NO₂) group has been replaced by an acetyl (COCH₃) group. It is described as having "reduced but still significant" potency compared to etonitazene itself. This compound was also tested as part of a series of cannabinoid receptor 2 agonists, and was found to be active though with fairly low potency of 960 nM at CB₂, and negligible activity at CB₁.

References

Lecolier S, Trouiller G (1967). "Nouveaux benzimidazoles doués d'activité morphinique" [New benzimidazoles with opioid activity.]. Chim. Ther. (in French). 2: 16–24.
Sparatore F, Boido V, Fanelli F (April 1968). "Dialchilamminoalchilbenzimidazoli d'interesse farmacologico [Dialkylaminoalkylbenzimidazoles of pharmacological interest" [Dialkylaminoalkylbenzimidazoles of pharmacological interest]. Il Farmaco; Edizione Scientifica (in Italian). 23 (4): 344–59. PMID 5680377.
"A review of the evidence on the use and harms of 2-benzyl benzimidazole ('nitazene') and piperidine benzimidazolone ('brorphine-like') opioids" (PDF). UK: Advisory Council on the Misuse of Drugs. July 2022.
Tonelli M, Cichero E, Mahmoud AM, Rabbito A, Tasso B, Fossa P, Ligresti A (December 2018). "Exploring the effectiveness of novel benzimidazoles as CB2 ligands: synthesis, biological evaluation, molecular docking studies and ADMET prediction". MedChemComm. 9 (12): 2045–2054. doi:10.1039/c8md00461g. PMC 6301267. PMID 30647880.