Basic information
- CAS
14680-51-4- Standard SMILES
CCN(CC)CCn1c(Cc2ccc(OC)cc2)nc2cc([N+](=O)[O-])ccc21- InChIKey
HNGZTLMRQTVPBH-UHFFFAOYSA-N- Molecular formula
- C21H26N4O3
- Average molar mass
- 382.5 g/mol
- Monoisotopic mass
- 382.2004907
Overview
Metonitazene is a member of the class of benzimidazoles that is 1H-benzimidazole substituted by 2-(diethylamino)ethyl, 4-methoxybenzyl, and nitro groups at positions 1, 2, and 5, respectively. It is a synthetic opioid. It has a role as an opioid analgesic and a mu-opioid receptor agonist. It is a member of benzimidazoles, a monomethoxybenzene, a C-nitro compound and a tertiary amino compound.
Names & identifiers
- Preferred name
- Metonitazene
- IUPAC
- N,N-diethyl-2-[2-[(4-methoxyphenyl)methyl]-5-nitrobenzimidazol-1-yl]ethanamine
- English name
- Metonitazene
- Molecular formula
- C21H26N4O3
- Molecular weight
- 382.46
Names & synonyms
metonitazene14680-51-4A7FF4K4CWBDEA NO. 9757DTXSID901336445N,N-diethyl-2-[2-[(4-methoxyphenyl)methyl]-5-nitrobenzimidazol-1-yl]ethanamineN,N-diethyl-2-(2-((4-methoxyphenyl)methyl)-5-nitrobenzimidazol-1-yl)ethanamineN,N-diethyl-2-(2-(4-methoxybenzyl)-5-nitro-1H-benzimidazol-1-yl)ethan-1-amineRefChem:158386DTXCID501766642UNII-A7FF4K4CWBCHEBI:234362
Show more names
Metonitazen(4-methoxyphenyl)methylMetonitaniMetanitazene1H-Benzimidazole-1-ethanamine, N,N-diethyl-2-[(4-methoxyphenyl)methyl]-5-nitro-
Benzimidazole, 1-(2-(diethylamino)ethyl)-2-(p-methoxybenzyl)-5-nitro-N,N-Diethyl-2-((4-methoxyphenyl)methyl)-5-nitro-1H-benzimidazole-1-ethanamineN,N-diethyl-2-[(4-methoxyphenyl)methyl]-5-nitro-1H-benzimidazole-1-ethanamine1H-Benzimidazole-1-ethanamine, N,N-diethyl-2-((4-methoxyphenyl)methyl)-5-nitro-1-(Diethylamino)ethyl-2-(4-methoxybenzyl)-5-nitrobenzimidazoleEpitope ID:2278939SCHEMBL30658738PAA68051
Database identifiers
Properties
Computed structural properties
- XLogP
- 3.9
- Topological polar surface area
- 76.1 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 5
- Rotatable bonds
- 8
- Heavy atoms
- 28
- Formal charge
- 0
- Complexity
- 489
Experimental & physicochemical properties
Drugs
DEA NFLIS-Drug Category -> Narcotic Analgesics
DEA Schedule I Controlled Substance -> Opiates
Physicochemical properties
- Boiling point
- 571.8 · 571.8±45.0 °C(Predicted)
- Density
- 1.19 · 1.19±0.1 g/cm3(Predicted)
- solubility
- 25 mg/ml; · DMF: 25 mg/ml; DMF:PBS (pH 7.2) (1:1): 0.5 mg/ml; DMSO: 20 mg/ml; Ethanol: 10 mg/ml
- pka
- 9.9 · 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
- FDA UNII
- 7 FF4K4CWB · A7FF4K4CWB
- Symbol(GHS)
- 2 · GHS02,GHS07
- Signal word
- Danger
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Hazard information
Regulatory InformationDEA schedule I controlled substance
Safety data
- Signal word
- Danger
- Symbol(GHS)
- GHS02,GHS07
- Hazard statements
- H225-H302+H312+H332-H319
- Precautionary statements
- P210-P233-P240-P241-P242-P243-P261-P264-P270-P271-P280-P301+P312-P303+P361+P353-P304+P340-P305+P351+P338-P321-P330-P362+P364-P337+P313-P370+P378-P403+P235-P501
Chemistry & industry
Applications
DescriptionMetonitazene 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.
UsesMetonitazene is an active analgesics with clinical applications.
Upstream & downstream products
Upstream raw materials
Related reactions
0 records
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Compound notes
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