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Benzimidazole opioids, also known as
nitazenes
Benzimidazole opioids, also known as nitazenes, are a class of synthetic opioids with an unusual benzimidazole structure often referred to as opioid New Psychoactive Substances (opioid NPS). First synthesized in the 1950s by CIBA Pharmaceuticals ...
, are a class of synthetic opioid
Opioids are substances that act on opioid receptors to produce morphine-like effects. Medically they are primarily used for pain relief, including anesthesia. Other medical uses include suppression of diarrhea, replacement therapy for opioi ...
s with an unusual benzimidazole
Benzimidazole is a heterocyclic aromatic organic compound. This bicyclic compound may be viewed as fused rings of the aromatic compounds benzene and imidazole. It is a colorless solid.
Preparation
Benzimidazole is produced by condensation of ...
structure often referred to as opioid New Psychoactive Substances (opioid NPS). First synthesized in the 1950s by CIBA Pharmaceuticals as potential analgesic medications, several substances in the class have been identified, the best known being etonitazene
Etonitazene is an analgesic drug, first reported in 1957, that has been shown to have approximately 1,000 to 1,500 times the potency of morphine in animals.
Because it is characterized by a strong dependency potential and a tendency to produce ...
. Like other synthetic opioids, benzimidazole opioids bind the mu-opioid receptor and may exhibit potency up to several hundred times that of morphine. While several substances in this class have found applications in research, they have never been used in clinical medicine due to their profound risk of respiratory depression and death, and have recently been recognized as emerging drugs of abuse. Isotonitazine was first identified in samples of illicit drugs, and implicated in opioid overdose deaths in Europe, Canada, and the United States beginning in 2019. Previously known nitazene analogs such as metonitazine and butonitazine, as well as novel nitazenes not previously patented, have since been discovered in toxicologic samples during forensic investigations.
The structure-activity relationship of the drug class has been explored to a reasonable extent. The optimal substitution pattern is fairly tightly defined (i.e. N,N-diethyl on the amine nitrogen, 4-ethoxy on the benzyl ring and 5-nitro on the benzimidazole ring), but even derivatives incorporating only some of these features are still potent opioids. If a methyl or carboxamide group is added on the alpha carbon of the benzyl group, or the benzyl is replaced by 2-phenylethyl, compounds of similar activity are obtained. Relative analgesic activity values are derived from tests on mice and cannot be extrapolated directly to humans, though the same general activity trends apply.
A 2019 publication has shown the possibility the previously assumed binding position of the benzimidazole class, acting as a semi-rigid fentanyl analogue may be incorrect. Based on a large scale analysis of known opioid receptor ligands a template was created through manual overlaying and alignment which has identified several mu-specific areas within the receptor. In this analysis, it is noted, etonitazene now more closely matches another, separate mu-specific region, sharing only a small area in common with the fentanyl class.
Table of benzimidazole opioids
See also
*25-NB
The 25-NB (25''x''-NB''x'') series, sometimes alternatively referred to as the NBOMe compounds, is a family of serotonergic psychedelics. They are substituted phenethylamines and were derived from the 2C family. They act as selective agonists of ...
* Arylcyclohexylamine
Arylcyclohexylamines, also known as arylcyclohexamines or arylcyclohexanamines, are a chemical class of pharmaceutical, designer, and experimental drugs.
History
Phencyclidine (PCP) is believed to be the first arylcyclohexylamine with recogniz ...
* List of aminorex analogues
This is a list of aminorex analogues. Aminorex itself is a stimulant drug with a 5-phenyl-2-amino-oxazoline structure. It was developed in the 1960s as an anorectic, but withdrawn from sale after it was discovered that extended use produced pulmon ...
* List of benzodiazepines
The below tables contain a sample list of benzodiazepines and benzodiazepine analogs that are commonly prescribed, with their basic pharmacological characteristics, such as half-life and equivalent doses to other benzodiazepines, also listed, alo ...
* List of fentanyl analogues
This is a list of fentanyl analogues (sometimes referred to as Fentalogs), including both compounds developed by pharmaceutical companies for legitimate medical use, and those which have been sold as designer drugs and reported to national drug co ...
* List of phenyltropanes
* Structural scheduling of synthetic cannabinoids To combat the illicit synthetic cannabinoid industry many jurisdictions have created a system to control these cannabinoids through their general (or Markush) structure as opposed to their specific identity. In this way new analogs are already cont ...
* Substituted cathinone
Substituted cathinones, which include some stimulants and entactogens, are derivatives of cathinone. They feature a phenethylamine core with an alkyl group attached to the alpha carbon, and a ketone group attached to the beta carbon, alon ...
References
{{reflist Lists of drugs Chemical classes of psychoactive drugs Synthetic opioids