U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ACHIRAL
Molecular Formula C22H28N4O3.ClH
Molecular Weight 432.944
Optical Activity UNSPECIFIED
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ETONITAZENE HYDROCHLORIDE

SMILES

Cl.CCOC1=CC=C(CC2=NC3=C(C=CC(=C3)[N+]([O-])=O)N2CCN(CC)CC)C=C1

InChI

InChIKey=JTBRYBUIGVMMQL-UHFFFAOYSA-N
InChI=1S/C22H28N4O3.ClH/c1-4-24(5-2)13-14-25-21-12-9-18(26(27)28)16-20(21)23-22(25)15-17-7-10-19(11-8-17)29-6-3;/h7-12,16H,4-6,13-15H2,1-3H3;1H

HIDE SMILES / InChI

Description

Etonitazene is a potent and selective mu-opioid agonist. It was developed in CIBA. Administration of etonitazene may induce respiratory depression, and therefor etonitazene is not used in humans. Etonitazene is explicitly listed as an illegal drug under UN convention and is illegal throughout the world.

CNS Activity

Originator

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
0.5 nM [Ki]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
PubMed

PubMed

TitleDatePubMed
Effects of etonitazene upon respiratory neurons.
1967 Jan 15
Photoactivatable opiate derivatives as irreversible probes of the mu-opioid receptor.
1990 Sep
Standard binding and functional assays related to medications development division testing for potential cocaine and opiate narcotic treatment medications.
1998 Mar
Intravenous self-administration of etonitazene alone and combined with cocaine in rhesus monkeys: comparison with heroin and antagonism by naltrexone and naloxonazine.
2009 Jun
Analgesic tolerance to high-efficacy agonists but not to morphine is diminished in phosphorylation-deficient S375A μ-opioid receptor knock-in mice.
2011 Sep 28
Patents

Sample Use Guides

In Vivo Use Guide
In rat tail-withdrawal assay, etonitazene was administered subcutaneously. ED50 was 0.38 mg/kg.
Route of Administration: subcutaneous
In Vitro Use Guide
Binding of etonitazene to mu-opioid receptors from the membrane fraction of rat brains (minus cerebellum) was studied using [3H]DAMGO as a radioligand. Etonitazene binds to mu-opioid receptors with Ki of 0.5 nM.
Name Type Language
ETONITAZENE HYDROCHLORIDE
MI  
Common Name English
1H-BENZIMIDAZOLE-1-ETHANAMINE, 2-((4-ETHOXYPHENYL)METHYL)-N,N-DIETHYL-5-NITRO-, MONOHYDROCHLORIDE
Common Name English
ETONITAZENE HYDROCHLORIDE [MI]
Common Name English
2-((4-ETHOXYPHENYL)METHYL)-N,N-DIETHYL-5-NITRO-1H-BENZIMIDAZOLE-1-ETHANAMINE HYDROCHLORIDE
Systematic Name English
C-20684
Code English
BENZIMIDAZOLE, 1-(2-(DIETHYLAMINO)ETHYL)-2-(P-ETHOXYBENZYL)-5-NITRO-, HYDROCHLORIDE
Common Name English
Code System Code Type Description
CAS
2053-25-0
Created by admin on Tue Oct 22 14:54:59 UTC 2019 , Edited by admin on Tue Oct 22 14:54:59 UTC 2019
PRIMARY
EPA CompTox
2053-25-0
Created by admin on Tue Oct 22 14:54:59 UTC 2019 , Edited by admin on Tue Oct 22 14:54:59 UTC 2019
PRIMARY
MERCK INDEX
M5197
Created by admin on Tue Oct 22 14:54:59 UTC 2019 , Edited by admin on Tue Oct 22 14:54:59 UTC 2019
PRIMARY Merck Index