| Systematic (IUPAC) name | |
|---|---|
| 2-(p-Ethoxybenzyl)-1-diethylaminoethyl-5-nitrobenzimidazole | |
| Clinical data | |
| Pregnancy cat. | ? |
| Legal status | Schedule I (CA) Schedule I (US) |
| Identifiers | |
| CAS number | 911-65-9 |
| ATC code | None |
| PubChem | CID 13493 |
| IUPHAR ligand | 1624 |
| DrugBank | DB01462 |
| ChemSpider | 12908 |
| UNII | 9U3GT3353T |
| ChEMBL | CHEMBL312040 |
| Chemical data | |
| Formula | C22H28N4O3 |
| Mol. mass | 396.48 g/mol |
| SMILES | eMolecules & PubChem |
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Etonitazene[1] is a potent analgesic drug shown to be approximately 1000–1500x the potency of morphine in animal models but only 60x morphine in man[2]. It is one of several benzimidazole opioids, and is structurally related to clonitazene (where the p-ethoxybenzyl group is replaced by a p-chlorobenzyl group. However, clonitazene itself has only 3x the potency of morphine.).
It has a strong dependency potential similar to that of morphine, and a strong tendency to produce respiratory depression, and is therefore not used in humans. It is however useful in addiction studies on animals. It is often used in studies requiring the animals to drink or ingest the opiate because it is not as bitter as the opiate salts, i.e., morphine sulfate.
It is the most potent benzimidazole opioid currently known.[3] Other analogues of considerable potency are as follows:
| Drug name | R | Analgesic Potency (Morphine = 1) |
|---|---|---|
| Etonitazene | ethoxy | 1000 |
| Clonitazene | chlorine | 3 |
| Nitazene | hydrogen | 2 |
| methyl | 10 | |
| ethyl | 30 | |
| propyl | 50 | |
| tert-butyl | 2 | |
| methoxy | 100 | |
| isopropoxy | 500 | |
| butoxy | 200 | |
| acetoxy | 5 | |
| methylthio | 50 | |
| ethylthio | 30 |
Of these analogues, only etonitazene and clonitazene are explicitly listed as illegal drugs under UN convention and so are illegal throughout the world. The rest would only be illegal in countries such as the USA, Australia and New Zealand that have laws equivalent to the Federal Analog Act.
Etonitazene has proved very important in mapping out the opiate receptor and some experimental compounds in which phenolic groupings have been replaced with nitro groupings have proved more active than the parent compound.
Illicit production and sale of etonitazene has been limited. This compound was identified on the illegal drug market in Moscow in 1998, appeared to have been illicitly manufactured, and was primarily smoked as pre-laced cigarettes.[4] In another case a chemist at Morton Thiokol called Thomas K Highsmith [5] produced the compound and placed it in a nasal inhaler.
Hunger, A.; Kebrle, J.; Rossi, A.; Hoffmann, K.; Experientia 1957, 13, 400.