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Record Information
Version1.0
Creation Date2009-06-18 21:54:32 UTC
Update Date2016-11-09 01:08:24 UTC
Accession NumberCHEM000921
Identification
Common Name[2-(Nitromethylene)-1-pyrrolidinyl]acetonitrile
ClassSmall Molecule
DescriptionAromatic 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. (1)
Contaminant Sources
  • T3DB toxins
Contaminant Type
  • Amine
  • Cyanide Compound
  • Nitrile
  • Nitromethylene
  • Organic Compound
  • Pesticide
  • Synthetic Compound
Chemical Structure
Thumb
SynonymsNot Available
Chemical FormulaC7H9N3O2
Average Molecular Mass167.168 g/mol
Monoisotopic Mass167.069 g/mol
CAS Registry Number91417-82-2
IUPAC Name2-[(2Z)-2-(nitromethylidene)pyrrolidin-1-yl]acetonitrile
Traditional Name2-[(2Z)-2-(nitromethylidene)pyrrolidin-1-yl]acetonitrile
SMILES[H]\C(=C1/CCCN1CC#N)N(=O)=O
InChI IdentifierInChI=1S/C7H9N3O2/c8-3-5-9-4-1-2-7(9)6-10(11)12/h6H,1-2,4-5H2/b7-6-
InChI KeyUUBCVVUIZRGQQU-SREVYHEPSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as n-alkylpyrrolidines. N-alkylpyrrolidines are compounds containing a pyrrolidine moiety that is substituted at the N1-position with an alkyl group. Pyrrolidine is a five-membered saturated aliphatic heterocycle with one nitrogen atom and four carbon atoms.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassPyrrolidines
Sub ClassN-alkylpyrrolidines
Direct ParentN-alkylpyrrolidines
Alternative Parents
Substituents
  • N-alkylpyrrolidine
  • C-nitro compound
  • Tertiary amine
  • Tertiary aliphatic amine
  • Alpha-aminonitrile
  • Organic nitro compound
  • Enamine
  • Carbonitrile
  • Nitrile
  • Organic oxoazanium
  • Allyl-type 1,3-dipolar organic compound
  • Propargyl-type 1,3-dipolar organic compound
  • Organic 1,3-dipolar compound
  • Azacycle
  • Organic oxygen compound
  • Organopnictogen compound
  • Organic oxide
  • Organic nitrogen compound
  • Amine
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External DescriptorsNot Available
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Cytoplasm
  • Extracellular
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility10.6 g/LALOGPS
logP-0.06ALOGPS
logP-0.22ChemAxon
logS-1.2ALOGPS
pKa (Strongest Basic)0.65ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area70.17 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity42.66 m³·mol⁻¹ChemAxon
Polarizability15.75 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0900000000-142fa19ff89eaf1dd360View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4l-0900000000-207770199e6edfabe174View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9200000000-ed5b48ed0ecabb197ff1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0900000000-dff7f289d2b4ef72d1bcView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-1900000000-45db41c471b8061ecbefView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-05mo-9500000000-a40a6af1a74c656ee884View in MoNA
Toxicity Profile
Route of ExposureNot Available
Mechanism of Toxicity Acts as a neurotransmitter mimic , having both excitatory and depressant effects, eventually blocking postsynaptic nicotinic receptors. (1) 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. (3)
MetabolismOrganic 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. (2)
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesNitromethylenes are used as pesticides. (1)
Minimum Risk LevelNot Available
Health EffectsNitromethylenes are neurotoxic. (1)
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDNot Available
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider IDNot Available
ChEBI IDNot Available
PubChem Compound ID2247078
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General ReferencesNot Available