Etonitazene

Etonitazene

Clinical data
ATC code	none
Legal status
Legal status	CA: Schedule I DE: Anlage I (Controlled) US: Schedule I
Identifiers
IUPAC name 2-(p-Ethoxybenzyl)-1-diethylaminoethyl-5-nitrobenzimidazole
CAS Number	911-65-9 N
PubChem CID	13493
IUPHAR/BPS	1624
DrugBank	DB01462 Y
ChemSpider	12908 Y
UNII	9U3GT3353T
ChEMBL	CHEMBL312040 Y
ECHA InfoCard	100.011.827
Chemical and physical data
Formula	C22H28N4O3
Molar mass	396.48 g/mol
3D model (Jmol)	Interactive image
SMILES CCOC1=CC=C(CC2=NC3=C(N2CCN(CC)CC)C=CC(N(=O)=O)=C3)C=C1
InChI InChI=1S/C22H28N4O3/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 Y Key:PXDBZSCGSQSKST-UHFFFAOYSA-N Y
NY (what is this?)

Etonitazene is a potent analgesic drug shown to be approximately 1000–1500x the potency of morphine in animal models but only 60x in man. 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).

Later work discovered that if a carboxide moiety is placed onto the carbon between the benzimidazole and the p-ethoxybenzyl, compounts up to 4x more potent were discovered It is of interest that the extra hydrogen-bond acceptor overlays the nociceptin receptor such as MCOPPB.

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. Other analogues of considerable potency are as follows:

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. In the United States it is a Schedule I Narcotic controlled substance with a DEA ACSCN of 9624 and a zero annual manufacturing quota as of 2013.

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.