Metonitazene

Metonitazene is an analgesic compound related to etonitazene,[2][3] which was first reported in 1957,[4] and has been shown to have approximately 100 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]

Metonitazene
Legal status
Legal status
Identifiers
IUPAC name
  • 2-[2-(4-Methoxybenzyl)-5-nitro-1H-benzimidazol-1-yl]-N,N-diethylethanamine
CAS Number
PubChem CID
ChemSpider
UNII
Chemical and physical data
FormulaC21H26N4O3
Molar mass382.464 g·mol−1
3D model (JSmol)
SMILES
  • CCN(CC)CCN1C2=C(C=C(C=C2)[N+](=O)[O-])N=C1CC3=CC=C(C=C3)OC
InChI
  • 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

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.

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.

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, Marthe M.; Van Uytfanghe, Katleen; Layle, Nathan K.; St. Germaine, Danielle M.; Iula, Donna M.; Stove, Christophe P. (March 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, István; Christie, Rachel; Evans-Brown, Michael; Gallegos, Ana; Jorge, Rita; de Morais, Joanna; Sedefov, Roumen (March 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): 400–1. 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. Bromig G (October 1958). "[New powerful analgetics and their clinical testing]". Klinische Wochenschrift. 36 (20): 960–3. doi:10.1007/bf01486702. PMID 13612082. S2CID 1023209.
  7. Krotulski, Alex J.; Papsun, Donna M.; Walton, Sara E.; Logan, Barry K. (June 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. ISSN 1942-7611. PMID 34137194. S2CID 235460764.
  8. Montanari, Eva; Madeo, Graziella; Pichini, Simona; Busardò, Francesco Paolo; Carlier, Jeremy (February 9, 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.
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