Metonitazene

Metonitazene
	File:Metonitazene.png
Identifiers
	IUPAC name 2-[2-(4-methoxybenzyl)-5-nitro-1H-benzimidazol-1-yl]-N,N-diethylethanamine;
CAS Number	14680-51-4;
PubChem CID	53316366;
CompTox Dashboard (EPA)	DTXSID901336445 ;
Chemical and physical data
Formula	C21H26N4O3
Molar mass	382.464 g·mol−1
3D model (JSmol)	Interactive image;
	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;

Metonitazene is an analgesic drug related to etonitazene, which was first reported in 1957,^[1] and has been shown to have approximately 100 times the potency of morphine by central routes of administration,^[2] but if used orally it has been shown to have approximately 10 times the potency of morphine.^[3]

Its effects are similar to other opioids like fentanyl and heroin, including analgesia, euphoria, sleepiness^[3]. 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 in pharmacotherapy.

References

^ 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.
^ 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.
^ ^a ^b Bromig G (October 1958). "[New powerful analgetics and their clinical testing]". Klinische Wochenschrift. 36 (20): 960–3. doi:10.1007/bf01486702. PMID 13612082.

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[1] 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.

[2] 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_1958-3] Bromig G (October 1958). "[New powerful analgetics and their clinical testing]". Klinische Wochenschrift. 36 (20): 960–3. doi:10.1007/bf01486702. PMID 13612082.

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See also

References