Metonitazene
[CAS# 14680-51-4]

Identification

• Classification: Pharmaceutical intermediate >> Heterocyclic compound intermediate >> Pyrimidine compound >> Amine
• Name: Metonitazene
• Synonyms: N,N-diethyl-2-[2-[(4-methoxyphenyl)methyl]-5-nitrobenzimidazol-1-yl]ethanamine
• Molecular Formula: C₂₁H₂₆N₄O₃
• Molecular Weight: 382.46
• CAS Registry Number: 14680-51-4
• SMILES: CCN(CC)CCN1C2=C(C=C(C=C2)[N+](=O)[O-])N=C1CC3=CC=C(C=C3)OC

Properties

• Density: 1.2±0.1 g/cm³, Calc.^*
• Index of Refraction: 1.597, Calc.^*
• Boiling Point: 571.8±45.0 ºC (760 mmHg), Calc.^*
• Flash Point: 299.6±28.7 ºC, Calc.^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Discovory and Applicatios

Metonitazene, a synthetic opioid, was first synthesized in the mid-1950s by a team of pharmaceutical chemists led by Dr. C. E. Winder at the pharmaceutical company CIBA (now part of Novartis). Initially developed for its potent analgesic properties, Metonitazene was one of several benzimidazole opioids researched during this period. Despite its powerful effects, its development did not progress into clinical use due to concerns about its high potency and potential for abuse, similar to other opioids. For many years, Metonitazene remained largely unknown outside scientific circles until its resurgence as a novel psychoactive substance in recent years.

In research settings, Metonitazene is studied to understand opioid receptor interactions, specifically its binding affinity to the mu-opioid receptor, which is responsible for its powerful analgesic effects. These studies contribute to the broader understanding of opioid pharmacodynamics and can inform the development of safer analgesics with fewer side effects.

Metonitazene has become increasingly relevant in forensic and toxicological contexts due to its emergence in the illicit drug market. Laboratories analyze biological samples for the presence of Metonitazene to aid in the diagnosis of overdoses and poisonings. The identification and quantification of this substance in forensic cases help public health officials track its spread and implement harm reduction strategies.

The resurgence of Metonitazene as a recreational drug has led to increased regulatory and law enforcement efforts. Agencies are working to classify Metonitazene under controlled substance laws to limit its availability and reduce the risk of abuse.

Despite its risks, there is ongoing interest in the therapeutic potential of Metonitazene analogs. Researchers are investigating modifications to its chemical structure to retain analgesic efficacy while minimizing adverse effects.

References

2024. Clinical and biochemical profile of a patient with acute metonitazene intoxication. Journal of the Neurological Sciences, 458.
DOI: 10.1016/j.jns.2024.122942

2023. Alkoxy chain length governs the potency of 2-benzylbenzimidazole 'nitazene' opioids associated with human overdose. Psychopharmacology, 240, 10.
DOI: 10.1007/s00213-023-06451-2

2021. Metonitazene in the United States-Forensic toxicology assessment of a potent new synthetic opioid using liquid chromatography mass spectrometry. Drug Testing and Analysis, 13, 9.
DOI: 10.1002/dta.3115