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PubChem

N,N-Diethyl-2-((4-(1-methylethoxy)phenyl)methyl)-5-nitro-1H-benzimidazole-1-ethanamine

PubChem CID
145721979
Structure
N,N-Diethyl-2-((4-(1-methylethoxy)phenyl)methyl)-5-nitro-1H-benzimidazole-1-ethanamine_small.png
N,N-Diethyl-2-((4-(1-methylethoxy)phenyl)methyl)-5-nitro-1H-benzimidazole-1-ethanamine_3D_Structure.png
Molecular Formula
Synonyms
  • Isotonitazene
  • 14188-81-9
  • ZFY1ZBQ8AV
  • N,N-diethyl-2-[[4-(1-methylethoxy)phenyl]methyl]-5-nitro-1H-benzimidazole-1-ethanamine
  • DTXSID201126188
Molecular Weight
410.5 g/mol
Computed by PubChem 2.2 (PubChem release 2025.09.15)
Dates
  • Create:
    2020-01-16
  • Modify:
    2026-05-30
Description
Isotonitazene is a member of the class of benzimidazoles that is 1H-benzimidazole substituted by 2-(diethylamino)ethyl, 4-(propan-2-yloxy)benzyl, 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, an aromatic ether, a C-nitro compound and a tertiary amino compound.
Isotonitazene is a DEA Schedule I controlled substance. Substances in the DEA Schedule I have no currently accepted medical use in the United States, a lack of accepted safety for use under medical supervision, and a high potential for abuse. It is a Opiates substance.
synthetic opioid

1 Structures

1.1 2D Structure

Chemical Structure Depiction
N,N-Diethyl-2-((4-(1-methylethoxy)phenyl)methyl)-5-nitro-1H-benzimidazole-1-ethanamine.png

1.2 3D Conformer

Interactive Chemical Structure Model
Conformer of 10

2 Names and Identifiers

2.1 Computed Descriptors

2.1.1 IUPAC Name

N,N-diethyl-2-[5-nitro-2-[(4-propan-2-yloxyphenyl)methyl]benzimidazol-1-yl]ethanamine
Computed by Lexichem TK 2.9.3 (PubChem release 2025.09.15)

2.1.2 InChI

InChI=1S/C23H30N4O3/c1-5-25(6-2)13-14-26-22-12-9-19(27(28)29)16-21(22)24-23(26)15-18-7-10-20(11-8-18)30-17(3)4/h7-12,16-17H,5-6,13-15H2,1-4H3
Computed by InChI 1.07.4 (PubChem release 2025.09.15)

2.1.3 InChIKey

OIOQREYBGDAYGT-UHFFFAOYSA-N
Computed by InChI 1.07.4 (PubChem release 2025.09.15)

2.1.4 SMILES

CCN(CC)CCN1C2=C(C=C(C=C2)[N+](=O)[O-])N=C1CC3=CC=C(C=C3)OC(C)C
Computed by OEChem 4.2.0 (PubChem release 2025.09.15)

2.2 Molecular Formula

C23H30N4O3
Computed by PubChem 2.2 (PubChem release 2025.09.15)

2.3 Other Identifiers

2.3.1 CAS

2.3.2 UNII

2.3.3 ChEBI ID

2.3.4 DEA Code Number

9614 (DEA schedule I controlled substance)

2.3.5 DSSTox Substance ID

2.3.6 KEGG ID

2.3.7 Nikkaji Number

2.3.8 Wikidata

2.3.9 Wikipedia

2.4 Synonyms

2.4.1 MeSH Entry Terms

isotonitazene

2.4.2 Depositor-Supplied Synonyms

3 Chemical and Physical Properties

3.1 Computed Properties

Property Name
Molecular Weight
Property Value
410.5 g/mol
Reference
Computed by PubChem 2.2 (PubChem release 2025.09.15)
Property Name
XLogP3-AA
Property Value
4.7
Reference
Computed by XLogP3 3.0 (PubChem release 2025.09.15)
Property Name
Hydrogen Bond Donor Count
Property Value
0
Reference
Computed by Cactvs 3.4.8.24 (PubChem release 2025.09.15)
Property Name
Hydrogen Bond Acceptor Count
Property Value
5
Reference
Computed by Cactvs 3.4.8.24 (PubChem release 2025.09.15)
Property Name
Rotatable Bond Count
Property Value
9
Reference
Computed by Cactvs 3.4.8.24 (PubChem release 2025.09.15)
Property Name
Exact Mass
Property Value
410.23179083 Da
Reference
Computed by PubChem 2.2 (PubChem release 2025.09.15)
Property Name
Monoisotopic Mass
Property Value
410.23179083 Da
Reference
Computed by PubChem 2.2 (PubChem release 2025.09.15)
Property Name
Topological Polar Surface Area
Property Value
76.1 Ų
Reference
Computed by Cactvs 3.4.8.24 (PubChem release 2025.09.15)
Property Name
Heavy Atom Count
Property Value
30
Reference
Computed by PubChem
Property Name
Formal Charge
Property Value
0
Reference
Computed by PubChem
Property Name
Complexity
Property Value
529
Reference
Computed by Cactvs 3.4.8.24 (PubChem release 2025.09.15)
Property Name
Isotope Atom Count
Property Value
0
Reference
Computed by PubChem
Property Name
Defined Atom Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Undefined Atom Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Defined Bond Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Undefined Bond Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Covalently-Bonded Unit Count
Property Value
1
Reference
Computed by PubChem
Property Name
Compound Is Canonicalized
Property Value
Yes
Reference
Computed by PubChem (release 2025.09.15)

3.2 Chemical Classes

3.2.1 Drugs

DEA NFLIS-Drug Category -> Narcotic Analgesics
DEA Schedule I Controlled Substance -> Opiates

4 Spectral Information

4.1 Mass Spectrometry

4.1.1 GC-MS

Technique
GC/MS
Source of Spectrum
DigiLab GmbH (C) 2024
Copyright
Copyright © 2024-2025 DigiLab GmbH and Wiley-VCH GmbH. All Rights Reserved.
Thumbnail
Thumbnail

6 Chemical Vendors

8 vendors
PubChem SID: 485289228
Purchasable Chemical: TRC-I141880
PubChem SID: 496048362
Purchasable Chemical: TRC-I141880-100MG
PubChem SID: 496048361
Purchasable Chemical: TRC-I141880-250MG
PubChem SID: 486051792
Purchasable Chemical: MC725612
PubChem SID: 480443883
Purchasable Chemical: 2023-05-1B018076
PubChem SID: 444137477
Purchasable Chemical: BA84099
PubChem SID: 470357560
Purchasable Chemical: CQ_14188-81-9
PubChem SID: 442921949
Purchasable Chemical: AA01LJ53
PubChem SID: 476156979
Purchasable Chemical: DY725612
PubChem SID: 505300814
Purchasable Chemical: PAA18881

7 Drug and Medication Information

7.1 DEA Drug and Chemical Information

DEA NFLIS Substance
Isotonitazene (Class: Narcotic Analgesics, Added Date: 01-2020)

Isotonitazene

(Street Names:Nitazene, “ISO”, Toni)

7.1.1 DEA Controlled Substances

Substance
Isotonitazene
Synonym(s)
N,N-diethyl-2-(2-(4-isopropoxybenzyl)-5-nitro-1H-benzimidazol-1-yl)ethan-1-amine
DEA Controlled Substances Code Number
9614
Controlled Substances Act Schedule
Schedule I - Substances in the DEA Schedule I have no currently accepted medical use in the United States, a lack of accepted safety for use under medical supervision, and a high potential for abuse.
Class
Opiates

8 Safety and Hazards

8.1 Regulatory Information

DEA Controlled Substances
DEA schedule I controlled substance

9 Literature

9.1 Consolidated References

20 items
Page of 4

9.2 NLM Curated PubMed Citations

9.3 Springer Nature References

9.4 Chemical Co-Occurrences in Literature

Chemical
Selected evidence
28 articles
View All
Chemical
Selected evidence
34 articles
View All
Chemical
Selected evidence
51 articles
View All

9.5 Chemical-Gene Co-Occurrences in Literature

Gene/Protein/Enzyme
Selected evidence
4 articles
View All
Gene/Protein/Enzyme
Selected evidence
3 articles
View All

9.6 Chemical-Disease Co-Occurrences in Literature

Disease
Selected evidence
28 articles
View All
Disease
Selected evidence
10 articles
View All
Disease
Selected evidence
6 articles
View All

9.7 Chemical-Organism Co-Occurrences in Literature

Organism
Selected evidence
22 articles
View All
Organism
Selected evidence
3 articles
View All
Organism
Selected evidence
7 articles
View All

10 Patents

10.1 Depositor-Supplied Patent Identifiers

268 items
Page of 54

10.2 Chemical Co-Occurrences in Patents

10.3 Chemical-Disease Co-Occurrences in Patents

Disease
Selected evidence
1 patent from 1 patent family
View All
Disease
Selected evidence
1 patent from 1 patent family
View All
Disease
Selected evidence
1 patent from 1 patent family
View All

10.4 Chemical-Gene Co-Occurrences in Patents

10.5 Chemical-Organism Co-Occurrences in Patents

11 Interactions and Pathways

11.1 Chemical-Target Interactions

6 items
Protein
Gene
Taxonomy
Action
Raclopride inhibits the reaction [isotonitazene results in increased expression of FOSB protein alternative form]isotonitazene results in increased expression of FOSB protein alternative formsch 23390 inhibits the reaction [isotonitazene results in increased expression of FOSB protein alternative form]
Evidence
Data Source
Protein
Gene
Taxonomy
Action
Isotonitazene results in increased activity of OPRM1 protein
Evidence
Data Source
Protein
Gene
Taxonomy
Action
Agonist
Evidence
Data Source
Page of 2

12 Classification

12.1 MeSH Tree

  • synthetic opioid
    MeSH Concept: M000738767
    MeSH Descriptor: C000710769

12.2 ChEBI Ontology

  • A member of the class of benzimidazoles that is 1H-benzimidazole substituted by 2-(diethylamino)ethyl, 4-(propan-2-yloxy)benzyl, and nitro groups at positions 1, 2, and 5, respectively. It is a synthetic opioid.

12.3 ChemIDplus

  • CTD
    Comparative Toxicogenomics Database - CTD selects and organizes gene, sequence, chemical, reference, and taxonomic data about gene-chemical interactions. It is hosted at North Carolina State University (NCSU).
  • DrugPortal
    Drug Information Portal - Portal to selected drug information from the U.S. National Library of Medicine and other key U.S. Government agencies
  • MeSH
    Medical Subject Heading and Supplementary Concept Records - ChemIDplus includes only the chemical names and chemical MeSH headings from this file. This search retrieves information from both MeSH headings andSupplementary Concept Records
  • PubChem
    PubChem Substance Database - The PubChem Substance Database contains the chemical structures of small organic molecules and information on their biological activities
  • PubMed
    PubMed - PubMed comprises over 20 million citations for biomedical literature from MEDLINE, life science journals, and online books
Page of 2

12.4 IUPHAR / BPS Guide to PHARMACOLOGY Target Classification

  • Opioid and opioid-like receptors are activated by a variety of endogenous peptides including [Met]enkephalin (met), [Leu]enkephalin (leu), β-endorphin (β-end), α-neodynorphin, dynorphin A (dynA), dynorphin B (dynB), big dynorphin (Big dyn), nociceptin/orphanin FQ (N/OFQ); endomorphin-1 and endomorphin-2 are also potential endogenous peptides. The Greek letter nomenclature for the opioid receptors, μ, δ and κ, is well established, and NC-IUPHAR considers this nomenclature appropriate, along with the symbols spelled out (mu, delta, and kappa), and the acronyms, MOP, DOP, and KOP. However the acronyms MOR, DOR and KOR are still widely used in the literature. The human N/OFQ receptor, NOP, is considered 'opioid-related' rather than opioid because, while it exhibits a high degree of structural homology with the conventional opioid receptors , it displays a distinct pharmacology. Currently there are numerous clinically used drugs, such as morphine and many other opioid analgesics, as well as antagonists such as naloxone. The majority of clinically used opiates are relatively selective μ agonists or partial agonists, though there are some μ/κ compounds, such as butorphanol, in clinical use. κ opioid agonists, such as the alkaloid nalfurafine and the peripherally acting peptide difelikefalin, are in clinical use for itch.

12.5 Drug Enforcement Administration (DEA) Classification

  • Schedule I
    Substances in the DEA Schedule I have no currently accepted medical use in the United States, a lack of accepted safety for use under medical supervision, and a high potential for abuse.
  • Substance Class: Opiates
  • Narcotic Analgesics
    NFLIS substances under class: Narcotic Analgesics

12.6 EPA DSSTox Classification

  • Short_Description: Wikipedia includes data for thousands of chemicals. ChemBoxes and DrugBoxes includes data such as CAS Registry Numbers, SMILES and InChIs.
  • Short_Description: FDA’s Global Substance Registration System Unique Ingredient Identifiers (UNIIs) file: April 12th 2021 download subset of chemicals with CASRN and/or structure SMILES
  • Short_Description: HighResNPS is a crowdsourced mass spectral database for HR-MS screening of New Psychoactive Substances (NPS).
  • Short_Description: The Scientific Working Group for the Analysis of Seized Drugs (SWGDRUG) mass spectral library
  • Short_Description: Schedule I drugs, substances, or chemicals are defined as drugs with no currently accepted medical use and a high potential for abuse.

12.7 MolGenie Organic Chemistry Ontology

  • drug like compounds
    Using a Fragment Based Druglikeness from OpenChemLib > -1
  • high risk irritant
  • benzenes
  • 1H-1,3-benzodiazoles
  • aryl alkyl ethers
Page of 2

12.8 Chemicals in PubChem from Regulatory Sources

  • Substances in the DEA Schedule I have no currently accepted medical use in the United States, a lack of accepted safety for use under medical supervision, and a high potential for abuse.

13 Information Sources

  1. CAS Common Chemistry
    LICENSE
    The data from CAS Common Chemistry is provided under a CC-BY-NC 4.0 license, unless otherwise stated.
    https://creativecommons.org/licenses/by-nc/4.0/
    N,N-Diethyl-2-[[4-(1-methylethoxy)phenyl]methyl]-5-nitro-1H-benzimidazole-1-ethanamine
    https://commonchemistry.cas.org/detail?cas_rn=14188-81-9
  2. ChemIDplus
    ChemIDplus Chemical Information Classification
    https://pubchem.ncbi.nlm.nih.gov/source/chemidplus
  3. EPA DSSTox
    N,N-Diethyl-2-[[4-(1-methylethoxy)phenyl]methyl]-5-nitro-1H-benzimidazole-1-ethanamine
    https://comptox.epa.gov/dashboard/DTXSID201126188
    CompTox Chemicals Dashboard Chemical Lists
    https://comptox.epa.gov/dashboard/chemical-lists/
  4. FDA Global Substance Registration System (GSRS)
    LICENSE
    Unless otherwise noted, the contents of the FDA website (www.fda.gov), both text and graphics, are not copyrighted. They are in the public domain and may be republished, reprinted and otherwise used freely by anyone without the need to obtain permission from FDA. Credit to the U.S. Food and Drug Administration as the source is appreciated but not required.
    https://www.fda.gov/about-fda/about-website/website-policies#linking
  5. ChEBI
  6. Drug Enforcement Administration (DEA)
    LICENSE
    Unless otherwise indicated, information on Department of Justice websites is in the public domain and may be copied and distributed without permission. Citation of the Department of Justice as source of the information is appreciated, as appropriate.
    https://www.justice.gov/legalpolicies
    DEA Drug and Chemical Classification
    https://www.dea.gov/drug-information/drug-scheduling
  7. Comparative Toxicogenomics Database (CTD)
    LICENSE
    It is to be used only for research and educational purposes. Any reproduction or use for commercial purpose is prohibited without the prior express written permission of NC State University.
    http://ctdbase.org/about/legal.jsp
  8. Drug Gene Interaction database (DGIdb)
    LICENSE
    The data used in DGIdb is all open access and where possible made available as raw data dumps in the downloads section.
    http://www.dgidb.org/downloads
  9. IUPHAR/BPS Guide to PHARMACOLOGY
    LICENSE
    The Guide to PHARMACOLOGY database is licensed under the Open Data Commons Open Database License (ODbL) https://opendatacommons.org/licenses/odbl/. Its contents are licensed under a Creative Commons Attribution-ShareAlike 4.0 International License (http://creativecommons.org/licenses/by-sa/4.0/)
    https://www.guidetopharmacology.org/about.jsp#license
    Guide to Pharmacology Target Classification
    https://www.guidetopharmacology.org/targets.jsp
  10. Japan Chemical Substance Dictionary (Nikkaji)
  11. KEGG
    LICENSE
    Academic users may freely use the KEGG website. Non-academic use of KEGG generally requires a commercial license
    https://www.kegg.jp/kegg/legal.html
  12. SpectraBase
  13. Springer Nature
  14. Wikidata
  15. Wikipedia
  16. Medical Subject Headings (MeSH)
    LICENSE
    Works produced by the U.S. government are not subject to copyright protection in the United States. Any such works found on National Library of Medicine (NLM) Web sites may be freely used or reproduced without permission in the U.S.
    https://www.nlm.nih.gov/copyright.html
  17. PubChem
    Chemicals in PubChem from Regulatory Sources
  18. MolGenie
    MolGenie Organic Chemistry Ontology
    https://github.com/MolGenie/ontology/
  19. NCBI
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