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. It is instead commonly used in the illicit manufacture of counterfit opioid pills such as OxyContin.

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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