Metonitazene - Misplaced Pages

Chemical compound (analgesic drug)

Pharmaceutical compound

Metonitazene
Legal status

Legal status	BR: Class F1 (Prohibited narcotics) DE: Anlage II (Authorized trade only, not prescriptible) UK: Class A US: Schedule I Illegal in Sweden
Identifiers
IUPAC name 2--N,N-diethylethanamine
CAS Number	14680-51-4
PubChem CID	53316366
ChemSpider	81407756
UNII	A7FF4K4CWB
KEGG	C22727
CompTox Dashboard (EPA)	DTXSID901336445
Chemical and physical data
Formula	C₂₁H₂₆N₄O₃
Molar mass	382.464 g·mol
3D model (JSmol)	Interactive image
SMILES CCN(CC)CCN1C2=C(C=C(C=C2)(=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

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

Its effects are similar to other opioids such as fentanyl and heroin, including analgesia, euphoria, and sleepiness. Adverse effects include vomiting, and respiratory depression that can potentially be fatal. 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.

Legal status

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.

References

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).
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.
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.
Hunger A, Kebrle J, Rossi A, Hoffmann K (October 1957). "". Experientia. 13 (10): 400–401. doi:10.1007/bf02161116. PMID 13473817. S2CID 32179439.
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.
^ Bromig G (October 1958). "". Klinische Wochenschrift. 36 (20): 960–963. doi:10.1007/bf01486702. PMID 13612082. S2CID 1023209.
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.
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.
"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.