<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <id type="integer">1049</id>
  <title>T3D1045</title>
  <common-name>2-[(2E)-2-(Nitromethylidene)pyrrolidin-1-yl]acetonitrile</common-name>
  <description>2-[(2E)-2-(Nitromethylidene)pyrrolidin-1-yl]acetonitrile (C7H9N3O2) is an exogenous organic compound with an average molecular weight of 167.17 g/mol. It exists as a solid at room temperature. 2-[(2E)-2-(Nitromethylidene)pyrrolidin-1-yl]acetonitrile belongs to the n-alkylpyrrolidines, a subclass of pyrrolidines within the organic compounds.

This organoheterocyclic compound acts as a neurotransmitter mimic that produces both excitatory and depressant effects, eventually blocking postsynaptic nicotinic receptors. It has five recorded protein targets: Acetylcholine receptor subunit beta (CHRNB1), Neuronal acetylcholine receptor subunit alpha-3 (CHRNA3), Neuronal acetylcholine receptor subunit alpha-4 (CHRNA4), Neuronal acetylcholine receptor subunit beta-2 (CHRNB2), and one other protein.</description>
  <cas>1164504-23-7</cas>
  <pubchem-id>2247080</pubchem-id>
  <chemical-formula>C7H9N3O2</chemical-formula>
  <weight>167.069480</weight>
  <appearance>White powder.</appearance>
  <melting-point></melting-point>
  <boiling-point></boiling-point>
  <density nil="true"/>
  <solubility></solubility>
  <specific-gravity nil="true"/>
  <flash-point nil="true"/>
  <vapour-pressure nil="true"/>
  <route-of-exposure></route-of-exposure>
  <target nil="true"/>
  <mechanism-of-toxicity>Acts as a neurotransmitter mimic , having both excitatory and depressant effects, eventually blocking postsynaptic nicotinic receptors. (T10) Organic nitriles decompose into cyanide ions both in vivo and in vitro. Consequently the primary mechanism of toxicity for organic nitriles is their production of toxic cyanide ions or hydrogen cyanide. Cyanide is an inhibitor of cytochrome c oxidase in the fourth complex of the electron transport chain (found in the membrane of the mitochondria of eukaryotic cells). It complexes with the ferric iron atom in this enzyme. The binding of cyanide to this cytochrome prevents transport of electrons from cytochrome c oxidase to oxygen. As a result, the electron transport chain is disrupted and the cell can no longer aerobically produce ATP for energy. Tissues that mainly depend on aerobic respiration, such as the central nervous system and the heart, are particularly affected. Cyanide is also known produce some of its toxic effects by binding to catalase, glutathione peroxidase, methemoglobin, hydroxocobalamin, phosphatase, tyrosinase, ascorbic acid oxidase, xanthine oxidase, succinic dehydrogenase, and Cu/Zn superoxide dismutase. Cyanide binds to the ferric ion of methemoglobin to form inactive cyanmethemoglobin. (L97)</mechanism-of-toxicity>
  <metabolism>Organic nitriles are converted into cyanide ions through the action of cytochrome P450 enzymes in the liver. Cyanide is rapidly absorbed and distributed throughout the body. Cyanide is mainly metabolized into thiocyanate by either rhodanese or 3-mercaptopyruvate sulfur transferase. Cyanide metabolites are excreted in the urine. (L96)</metabolism>
  <toxicity></toxicity>
  <lethaldose></lethaldose>
  <carcinogenicity>No indication of carcinogenicity to humans (not listed by IARC).</carcinogenicity>
  <use-source>Nitromethylenes are used as pesticides. (T10)</use-source>
  <min-risk-level></min-risk-level>
  <health-effects>Nitromethylenes are neurotoxic. (T10)</health-effects>
  <symptoms></symptoms>
  <treatment></treatment>
  <created-at type="dateTime">2009-06-18T21:54:31Z</created-at>
  <updated-at type="dateTime">2026-04-05T15:25:51Z</updated-at>
  <interacting-proteins nil="true"/>
  <wikipedia></wikipedia>
  <uniprot-id></uniprot-id>
  <kegg-compound-id></kegg-compound-id>
  <omim-id></omim-id>
  <chebi-id></chebi-id>
  <biocyc-id></biocyc-id>
  <ctd-id></ctd-id>
  <stitch-id>2-[(2E)-2-(Nitromethylidene)pyrrolidin-1-yl]acetonitrile</stitch-id>
  <drugbank-id></drugbank-id>
  <pdb-id></pdb-id>
  <actor-id></actor-id>
  <organism nil="true"/>
  <export type="boolean">true</export>
  <metabolizing-proteins nil="true"/>
  <transporting-proteins nil="true"/>
  <moldb-smiles>[H]\C(=C1\CCCN1CC#N)N(=O)=O</moldb-smiles>
  <moldb-formula>C7H9N3O2</moldb-formula>
  <moldb-inchi>InChI=1S/C7H9N3O2/c8-3-5-9-4-1-2-7(9)6-10(11)12/h6H,1-2,4-5H2/b7-6+</moldb-inchi>
  <moldb-inchikey>UUBCVVUIZRGQQU-VOTSOKGWSA-N</moldb-inchikey>
  <moldb-average-mass type="decimal">167.1653</moldb-average-mass>
  <moldb-mono-mass type="decimal">167.069476547</moldb-mono-mass>
  <origin>Exogenous</origin>
  <state>Solid</state>
  <logp></logp>
  <hmdb-id></hmdb-id>
  <chembl-id>CHEMBL1340003</chembl-id>
  <chemspider-id>1681490</chemspider-id>
  <structure-image-file-name nil="true"/>
  <structure-image-content-type nil="true"/>
  <structure-image-file-size type="integer" nil="true"/>
  <structure-image-updated-at type="dateTime" nil="true"/>
  <biodb-id nil="true"/>
  <synthesis-reference></synthesis-reference>
  <structure-image-caption nil="true"/>
  <chemdb-id>CHEM000902</chemdb-id>
  <dsstox-id>DTXSID60897074</dsstox-id>
  <toxcast-id nil="true"/>
  <stoff-ident-origin nil="true"/>
  <stoff-ident-id nil="true"/>
  <susdat-id>NS00075488</susdat-id>
  <iupac nil="true"/>
  <moldb-polar-surface-area>72.85</moldb-polar-surface-area>
  <moldb-refractivity>43.65970000000001</moldb-refractivity>
  <moldb-polarizability>15.851930612280828</moldb-polarizability>
  <moldb-rotatable-bond-count>2</moldb-rotatable-bond-count>
  <moldb-acceptor-count>4</moldb-acceptor-count>
  <moldb-donor-count>0</moldb-donor-count>
  <moldb-pka-strongest-acidic nil="true"/>
  <moldb-pka-strongest-basic>0.9899783410613345</moldb-pka-strongest-basic>
  <moldb-physiological-charge>0</moldb-physiological-charge>
  <moldb-number-of-rings>1</moldb-number-of-rings>
  <moldb-alogps-logp>-0.06</moldb-alogps-logp>
  <moldb-alogps-logs>-1.20</moldb-alogps-logs>
  <moldb-alogps-solubility>1.06e+01 g/l</moldb-alogps-solubility>
  <kingdom>Organic compounds</kingdom>
  <superklass>Organoheterocyclic compounds</superklass>
  <klass>Pyrrolidines</klass>
  <subklass>N-alkylpyrrolidines</subklass>
  <paper-count type="integer">0</paper-count>
  <sync-id>CED0083064</sync-id>
  <structure-inchikey>UUBCVVUIZRGQQU-VOTSOKGWSA-N</structure-inchikey>
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</structure-pickle>
  <structure-indexed-at type="dateTime">2026-09-19T03:59:58Z</structure-indexed-at>
</compound>
