Methionitazene

Methionitazene
Identifiers
	IUPAC name N,N-diethyl-2-[2-[(4-methylsulfanylphenyl)methyl]-5-nitrobenzimidazol-1-yl]ethanamine;
CAS Number	102471-37-4;
PubChem CID	162623790;
ChemSpider	129433071;
UNII	JW27AV47BF;
Chemical and physical data
Formula	C21H26N4O2S
Molar mass	398.53 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)SC;
	InChI InChI=1S/C21H26N4O2S/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:ODVCNMQMXRKHGM-UHFFFAOYSA-N;

Methionitazene (Methylthionitazene) is a benzimidazole derivative which is an opioid designer drug. It was invented in the late 1950s as part of the original research into the "nitazene" group of opioids by CIBA in Switzerland, but as with all compounds from this group was never developed for legitimate medical uses. In early studies on mice, it was found to be around half the potency of the methoxy analogue metonitazene with around 50x the analgesic potency of morphine, and significantly more potent than the ethylthio homologue,^[1] but more recent research using modern techniques found methionitazene and metonitazene to have a similar EC₅₀ in vitro despite the methoxy compound having a stronger binding affinity at the mu opioid receptor.^[2]

References

^ Hunger A, Kebrle J, Rossi A, Hoffmann K (1960). "Benzimidazole-Derivate und verwandte Heterocyclen III. Synthese von 1-Aminoalkyl-2-benzyl-nitro-benzimidazolen". Helvetica Chimica Acta. 43 (4): 1032–1046. doi:10.1002/hlca.19600430412.
^ Vandeputte MM, Glatfelter GC, Walther D, Layle NK, St Germaine DM, Ujváry I, et al. (December 2024). "Characterization of novel nitazene recreational drugs: Insights into their risk potential from in vitro µ-opioid receptor assays and in vivo behavioral studies in mice". Pharmacological Research. 210 107503: 107503. doi:10.1016/j.phrs.2024.107503. PMC 11655282. PMID 39521025.

[1] Hunger A, Kebrle J, Rossi A, Hoffmann K (1960). "Benzimidazole-Derivate und verwandte Heterocyclen III. Synthese von 1-Aminoalkyl-2-benzyl-nitro-benzimidazolen". Helvetica Chimica Acta. 43 (4): 1032–1046. doi:10.1002/hlca.19600430412.

[2] Vandeputte MM, Glatfelter GC, Walther D, Layle NK, St Germaine DM, Ujváry I, et al. (December 2024). "Characterization of novel nitazene recreational drugs: Insights into their risk potential from in vitro µ-opioid receptor assays and in vivo behavioral studies in mice". Pharmacological Research. 210 107503: 107503. doi:10.1016/j.phrs.2024.107503. PMC 11655282. PMID 39521025.

[1]

[2]

See also

References