| Chemical Properties | Back Directory | [Boiling point ]
571.8±45.0 °C(Predicted) | [density ]
1.19±0.1 g/cm3(Predicted) | [solubility ]
DMF: 25 mg/ml; DMF:PBS (pH 7.2) (1:1): 0.5 mg/ml; DMSO: 20 mg/ml; Ethanol: 10 mg/ml | [pka]
9.90±0.25(Predicted) | [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 | [InChIKey]
HNGZTLMRQTVPBH-UHFFFAOYSA-N | [SMILES]
C1(CC2=CC=C(OC)C=C2)N(CCN(CC)CC)C2=CC=C([N+]([O-])=O)C=C2N=1 |
| Hazard Information | Back Directory | [Description]
Metonitazene(14680-51-4) is an analgesic drug related to etonitazene and was first synthesized in the late 1950s by a Swiss chemical company in an effort to develop novel opioid alternatives to morphine. Metonitazene has been shown to have approximately 100 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.
| [Chemical Properties]
Metonitazene is classified as a novel opioid but is dissimilar from fentanyl and U-series analogues. Metonitazene, has been described as a white or off-white/beige powder, sometimes referred to as crystalline in consistency (Cayman Chemicals, 2020; Krotulski et al., 2021; PubChem, 2020). The free base and the hydrochloride salt appear as a white or colored powder. The citrate salt is described as a crystalline solid (Cayman, 2021a). | [Uses]
Metonitazene is an active analgesics with clinical applications. | [Health effects]
Metonitazene is considered a new psychoactive substance (NPS) and emerging potent synthetic opioid, causing increased public health concern beginning in 2020. Effects of Metonitazene are similar to other opioids and include pain relief, a sense of euphoria and sleepiness. It also causes vomiting and can slow respiratory rates, sometimes to dangerously low levels. | [Biological Activity]
Metonitazene (MTZ) is one of the newest non-fentanyl NSOs that has emerged in the illicit drug market followed by other analogues of nitazenes such as N-Piperidinyl etonitazene. MTZ, bearing a 4-methoxyphenyl group instead of the 4-isopropoxyphenyl moiety of ITZ, is internationally scheduled since June 2022. Metonitazene act as potent μ-opioid receptor agonist. MTZ is a high affinity ligand and potent MOR agonist at both native and recombinant MOR systems. It stimulate in vivo DA transmission in the NAc shell within a range of dosages able to reduce behavioral activity, and comparable with the concentration used for in vitro studies to determine affinity, potency and efficacy[6]. | [References]
1. Vandeputte, M.M., Van Uytfanghe, K., Layle, N.K., et al. Synthesis, chemical characterization, and μ-opioid receptor activity assessment of the emerging group of "nitazene" 2-benzylbenzimidazole synthetic opioids. ACS Chem. Neurosci. 12(7), 1241-1251 (2021). DOI:10.22541/AU.160520665.59016513/V2
2. Ujváry, I., Christie, R., Evans-Brown, M., et al. DARK classics in chemical neuroscience: Etonitazene and related benzimidazoles. ACS Chem. Neurosci. 12(7), 1072-1092 (2021). DOI:10.1021/acschemneuro.1c00037
3. Metonitazene in the United States-Forensic toxicology assessment of a potent new synthetic opioid using liquid chromatography mass spectrometry DOI:10.1002/dta.3115
4. Pharmacological characterization of novel synthetic opioids: Isotonitazene, Metonitazene, and piperidylthiambutene as potent μ-opioid receptor agonists DOI:10.1016/j.neuropharm.2022.109263
5. https://www.overdosepreventionstrategies.org/glossary/metonitazene/ |
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