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1H-3-Benzazepine, 2,3,4,5-tetrahydro-2-(nitromethylene)-

PubChem CID
3045196
Structure
1H-3-Benzazepine, 2,3,4,5-tetrahydro-2-(nitromethylene)-_small.png
1H-3-Benzazepine, 2,3,4,5-tetrahydro-2-(nitromethylene)-_3D_Structure.png
Molecular Formula
Synonyms
  • BRN 1645742
  • 1H-3-Benzazepine, 2,3,4,5-tetrahydro-2-(nitromethylene)-
  • 2-(Nitromethylene)-2,3,4,5-tetrahydro-1H-3-benzazepine
  • 58350-08-6
  • DTXSID10897069
Molecular Weight
204.22 g/mol
Computed by PubChem 2.2 (PubChem release 2024.11.20)
Dates
  • Create:
    2005-08-09
  • Modify:
    2025-01-18
Description
Aromatic heterocycle containing a nitromethylene substituent. Fast acting neurotoxicant, effective both by contact or oral ingestion; they are relatively safe to vertebrates and degrade rapidly in the environment. (T10)
T10: Casarett LJ, Klaassen CD, and Watkins JB (2003). Casarett and Doull's essentials of toxicology. New York: McGraw-Hill/Medical Pub. Div.

1 Structures

1.1 2D Structure

Chemical Structure Depiction
1H-3-Benzazepine, 2,3,4,5-tetrahydro-2-(nitromethylene)-.png

1.2 3D Conformer

2 Names and Identifiers

2.1 Computed Descriptors

2.1.1 IUPAC Name

(4E)-4-(nitromethylidene)-1,2,3,5-tetrahydro-3-benzazepine
Computed by Lexichem TK 2.7.0 (PubChem release 2024.11.20)

2.1.2 InChI

InChI=1S/C11H12N2O2/c14-13(15)8-11-7-10-4-2-1-3-9(10)5-6-12-11/h1-4,8,12H,5-7H2/b11-8+
Computed by InChI 1.07.0 (PubChem release 2024.11.20)

2.1.3 InChIKey

WBGHUVVRWWHCDW-DHZHZOJOSA-N
Computed by InChI 1.07.0 (PubChem release 2024.11.20)

2.1.4 SMILES

C1CN/C(=C/[N+](=O)[O-])/CC2=CC=CC=C21
Computed by OEChem 2.3.0 (PubChem release 2024.12.12)

2.2 Molecular Formula

C11H12N2O2
Computed by PubChem 2.2 (PubChem release 2024.11.20)

2.3 Other Identifiers

2.3.1 CAS

58350-08-6

2.3.2 DSSTox Substance ID

2.3.3 Wikidata

2.4 Synonyms

2.4.1 Depositor-Supplied Synonyms

3 Chemical and Physical Properties

3.1 Computed Properties

Property Name
Molecular Weight
Property Value
204.22 g/mol
Reference
Computed by PubChem 2.2 (PubChem release 2024.11.20)
Property Name
XLogP3-AA
Property Value
2.3
Reference
Computed by XLogP3 3.0 (PubChem release 2024.11.20)
Property Name
Hydrogen Bond Donor Count
Property Value
1
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2024.11.20)
Property Name
Hydrogen Bond Acceptor Count
Property Value
3
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2024.11.20)
Property Name
Rotatable Bond Count
Property Value
0
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2024.11.20)
Property Name
Exact Mass
Property Value
204.089877630 Da
Reference
Computed by PubChem 2.2 (PubChem release 2024.11.20)
Property Name
Monoisotopic Mass
Property Value
204.089877630 Da
Reference
Computed by PubChem 2.2 (PubChem release 2024.11.20)
Property Name
Topological Polar Surface Area
Property Value
57.9 Ų
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2024.11.20)
Property Name
Heavy Atom Count
Property Value
15
Reference
Computed by PubChem
Property Name
Formal Charge
Property Value
0
Reference
Computed by PubChem
Property Name
Complexity
Property Value
270
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2024.11.20)
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
1
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 2021.10.14)

5 Chemical Vendors

6 Use and Manufacturing

6.1 Uses

Nitromethylenes are used as pesticides. (T10)
T10: Casarett LJ, Klaassen CD, and Watkins JB (2003). Casarett and Doull's essentials of toxicology. New York: McGraw-Hill/Medical Pub. Div.

7 Toxicity

7.1 Toxicological Information

7.1.1 Toxicity Summary

Acts as a neurotransmitter mimic , having both excitatory and depressant effects, eventually blocking postsynaptic nicotinic receptors. (T10)
T10: Casarett LJ, Klaassen CD, and Watkins JB (2003). Casarett and Doull's essentials of toxicology. New York: McGraw-Hill/Medical Pub. Div.

7.1.2 Carcinogen Classification

Carcinogen Classification
No indication of carcinogenicity to humans (not listed by IARC).

7.1.3 Health Effects

Nitromethylenes are neurotoxic. (T10)
T10: Casarett LJ, Klaassen CD, and Watkins JB (2003). Casarett and Doull's essentials of toxicology. New York: McGraw-Hill/Medical Pub. Div.

7.1.4 Acute Effects

8 Literature

8.1 Consolidated References

8.2 Chemical Co-Occurrences in Literature

9 Interactions and Pathways

9.1 Chemical-Target Interactions

10 Classification

10.1 ChemIDplus

10.2 NORMAN Suspect List Exchange Classification

10.3 EPA DSSTox Classification

10.4 MolGenie Organic Chemistry Ontology

11 Information Sources

  1. ChemIDplus
    1H-3-Benzazepine, 2,3,4,5-tetrahydro-2-(nitromethylene)-
    https://pubchem.ncbi.nlm.nih.gov/substance/?source=chemidplus&sourceid=0058350086
    ChemIDplus Chemical Information Classification
    https://pubchem.ncbi.nlm.nih.gov/source/ChemIDplus
  2. EPA DSSTox
    1H-3-Benzazepine, 2,3,4,5-tetrahydro-2-(nitromethylene)-
    https://comptox.epa.gov/dashboard/DTXSID10897069
    CompTox Chemicals Dashboard Chemical Lists
    https://comptox.epa.gov/dashboard/chemical-lists/
  3. Toxin and Toxin Target Database (T3DB)
    LICENSE
    T3DB is offered to the public as a freely available resource. Use and re-distribution of the data, in whole or in part, for commercial purposes requires explicit permission of the authors and explicit acknowledgment of the source material (T3DB) and the original publication.
    http://www.t3db.ca/downloads
    (4E)-4-(Nitromethylidene)-1,2,3,5-tetrahydro-3-benzazepine
    http://www.t3db.ca/toxins/T3D1054
  4. Wikidata
    (4E)-4-(nitromethylidene)-1,2,3,5-tetrahydro-3-benzazepine
    https://www.wikidata.org/wiki/Q76151125
  5. PubChem
  6. NORMAN Suspect List Exchange
    LICENSE
    Data: CC-BY 4.0; Code (hosted by ECI, LCSB): Artistic-2.0
    https://creativecommons.org/licenses/by/4.0/
    NORMAN Suspect List Exchange Classification
    https://www.norman-network.com/nds/SLE/
  7. MolGenie
    MolGenie Organic Chemistry Ontology
    https://github.com/MolGenie/ontology/
CONTENTS