Chemistry:Etonitazene 5-acetyl analogue

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Short description: Chemical compound
Etoacetazene
Etoacetazene structure.png
Identifiers
CAS Number
PubChem CID
ChemSpider
ChEMBL
Chemical and physical data
FormulaC24H31N3O2
Molar mass393.531 g·mol−1
3D model (JSmol)

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 It is an analogue of etonitazene where the 5-nitro (NO2) group has been replaced by an acetyl (COCH3) group.[1][2] It is described as having "reduced but still significant" potency compared to etonitazene itself.[3] This compound was also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.[4]

See also

References

  1. "Nouveaux benzimidazoles doués d'activité morphinique." (in French). Chim. Ther. 2: 16–24. 1967. 
  2. "Dialchilamminoalchilbenzimidazoli d'interesse farmacologico [Dialkylaminoalkylbenzimidazoles of pharmacological interest" (in Italian). Il Farmaco; Edizione Scientifica 23 (4): 344–59. April 1968. PMID 5680377. 
  3. "A review of the evidence on the use and harms of 2-benzyl benzimidazole ('nitazene') and piperidine benzimidazolone ('brorphine-like') opioids.". UK: Advisory Council on the Misuse of Drugs. July 2022. https://assets.publishing.service.gov.uk/government/uploads/system/uploads/attachment_data/file/1091152/ACMD_advice_on_2-benzyl_benzimidazole_and_piperidine_benzimidazolone_opioids.pdf. 
  4. "Exploring the effectiveness of novel benzimidazoles as CB2 ligands: synthesis, biological evaluation, molecular docking studies and ADMET prediction". MedChemComm 9 (12): 2045–2054. December 2018. doi:10.1039/c8md00461g. PMID 30647880.