3883. Etonitazene

Nomenclature

CAS number: 911-65-9
2-[(4-Ethoxyphenyl)methyl]-N,N-diethyl-5-nitro-1H-benzimidazole-1-ethanamine; 1-[(2-diethylamino)ethyl]-2-(p-ethoxybenzyl)-5-nitrobenzimidazole; 2-p-ethoxybenzyl-1-(2-diethylaminoethyl)-5-nitrobenzimidazole.
C22H28N4O3; mol wt 396.48.
C 66.65%, H 7.12%, N 14.13%, O 12.11%.

Description and references

Opioid analgesic. Prepn: Hunger et al., Experientia 13, 400 (1957); Hoffmann et al., US 2935514 (1960 to Ciba); F. I. Carroll, M. C. Coleman, J. Med. Chem. 18, 318 (1975). Crystal structure: C. Humblet et al., Acta Crystallogr. B34, 3828 (1978). Binds selectively to mu-opioid receptors: M. S. Moolten et al., Life Sci. 52, PL199 (1993).

Chemical structure

Properties

Needles from ether-petroleum ether, mp 77-78°.

Derivative

Hydrochloride.

Nomenclature

CAS number: 2053-25-0
C22H28N4O3.HCl; mol wt 432.94.
C 61.03%, H 6.75%, N 12.94%, O 11.09%, Cl 8.19%.

Properties

Crystals from abs ethanol, mp 163-164.5°.

Note

This is a controlled substance (opiate): 21 CFR, 1308.11.

Use

Reinforcer in animal models of drug addiction.