Metonitazene

Last updated

Metonitazene
Metonitazene.svg
Legal status
Legal status
Identifiers
  • 2-[2-(4-Methoxybenzyl)-5-nitro-1H-benzimidazol-1-yl]-N,N-diethylethanamine
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
ChEBI
CompTox Dashboard (EPA)
Chemical and physical data
Formula C21H26N4O3
Molar mass 382.464 g·mol−1
3D model (JSmol)
  • CCN(CC)CCN1C2=C(C=C(C=C2)[N+](=O)[O-])N=C1CC3=CC=C(C=C3)OC
  • InChI=1S/C21H26N4O3/c1-4-23(5-2)12-13-24-20-11-8-17(25(26)27)15-19(20)22-21(24)14-16-6-9-18(28-3)10-7-16/h6-11,15H,4-5,12-14H2,1-3H3
  • Key:HNGZTLMRQTVPBH-UHFFFAOYSA-N

Metonitazene is an analgesic compound related to etonitazene, [2] [3] which was first reported in 1957, [4] and has been shown to have approximately 1000 times the potency of morphine by central routes of administration, [5] but if used orally it has been shown to have approximately 10 times the potency of morphine. [6]

Contents

Its effects are similar to other opioids such as fentanyl and heroin, including analgesia, euphoria, and sleepiness. [6] [7] Adverse effects include vomiting, and respiratory depression that can potentially be fatal. [8] Because of high dependency potential and dangerous adverse effects it has never been introduced into pharmacotherapy. It is instead commonly used in the illicit manufacture of counterfeit oxycodone opioid pills. [9]

In the United States, metonitazene is a Schedule I controlled substance under the Controlled Substances Act.

Metonitazene is not controlled under the 1971 Convention on Psychotropic Substances; however, in many countries possession or intent to sell for human consumption might be prosecuted under several analog acts.

Metonitazene became a Class A drug in the UK on 20th March 2024.

See also

References

  1. Riksdagsförvaltningen. "Förordning (1992:1554) om kontroll av narkotika Svensk författningssamling 1992:1992:1554 t.o.m. SFS 2021:301 - Riksdagen". www.riksdagen.se (in Swedish).
  2. Vandeputte MM, Van Uytfanghe K, Layle NK, St Germaine DM, Iula DM, Stove CP (April 2021). "Synthesis, Chemical Characterization, and μ-Opioid Receptor Activity Assessment of the Emerging Group of "Nitazene" 2-Benzylbenzimidazole Synthetic Opioids". ACS Chemical Neuroscience. 12 (7): 1241–1251. doi:10.1021/acschemneuro.1c00064. hdl: 1854/LU-8714061 . PMID   33759494. S2CID   232337929.
  3. Ujváry I, Christie R, Evans-Brown M, Gallegos A, Jorge R, de Morais J, Sedefov R (April 2021). "DARK Classics in Chemical Neuroscience: Etonitazene and Related Benzimidazoles". ACS Chemical Neuroscience. 12 (7): 1072–1092. doi:10.1021/acschemneuro.1c00037. PMID   33760580. S2CID   232356192.
  4. Hunger A, Kebrle J, Rossi A, Hoffmann K (October 1957). "[Synthesis of analgesically active benzimidazole derivatives with basic substitutions]". Experientia. 13 (10): 400–401. doi:10.1007/bf02161116. PMID   13473817. S2CID   32179439.
  5. Hunger VA, Kebrle J, Rossi A, Hoffmann K (1960). "Benzimidazol-Derivate und verwandte Heterocyclen III. Synthese von 1-Aminoalkyl-2-nenzyl-nitro-benzimidazolen". Helvetica Chimica Acta. 43 (4): 1032–1046. doi:10.1002/hlca.19600430412.
  6. 1 2 Bromig G (October 1958). "[New powerful analgetics and their clinical testing]". Klinische Wochenschrift. 36 (20): 960–963. doi:10.1007/bf01486702. PMID   13612082. S2CID   1023209.
  7. Krotulski AJ, Papsun DM, Walton SE, Logan BK (October 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 (10): 1697–1711. doi:10.1002/dta.3115. PMID   34137194. S2CID   235460764.
  8. Montanari E, Madeo G, Pichini S, Busardò FP, Carlier J (August 2022). "Acute Intoxications and Fatalities Associated With Benzimidazole Opioid (Nitazene Analog) Use: A Systematic Review". Therapeutic Drug Monitoring. 44 (4): 494–510. doi:10.1097/FTD.0000000000000970. PMID   35149665. S2CID   246776288.
  9. "A synthetic opioid stronger than fentanyl and hundreds of times more potent than heroin is emerging in Australia". ABC News. 24 June 2024. Retrieved 25 June 2024.