Etoacetazene

Last updated
Etoacetazene
Etoacetazene structure.png
Identifiers
  • 1-[1-[2-(diethylamino)ethyl]-2-[(4-ethoxyphenyl)methyl]benzimidazol-5-yl]ethanone
CAS Number
PubChem CID
ChemSpider
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
Formula C24H31N3O2
Molar mass 393.531 g·mol−1
3D model (JSmol)
  • CCN(CC)CCN1C2=C(C=C(C=C2)C(=O)C)N=C1CC3=CC=C(C=C3)OCC
  • 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

Etoacetazene (Etonitazene 5-acetyl analogue, 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 It is an analogue of etonitazene where the 5-nitro (NO2) group has been replaced by an acetyl (COCH3) group.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. ↑ Lecolier S, Trouiller G (1967). "Nouveaux benzimidazoles doués d'activité morphinique" [New benzimidazoles with opioid activity.]. Chim. Ther. (in French). 2: 16–24.
  2. ↑ 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.
  3. ↑ "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.
  4. ↑ 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.



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