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Record Information
Version2.0
Creation Date2009-07-03 20:54:23 UTC
Update Date2014-12-24 20:25:31 UTC
Accession NumberT3D2453
Identification
Common NameGyromitrin
ClassSmall Molecule
DescriptionGyromitrin is found in mushrooms. Toxin from the fungus Gyromitra esculenta. Freq. cause of mushroom poisoning Gyromitrin is a toxin and possible carcinogen present in most members of the fungal genus Gyromitra, most notably the false morel G. esculenta.
Compound Type
  • Food Toxin
  • Fungal Toxin
  • Hydrazine
  • Metabolite
  • Mycotoxin
  • Natural Compound
  • Organic Compound
Chemical Structure
Thumb
Synonyms
Synonym
Acetaldehyde formylmethylhydrazone
Acetaldehyde methylformylhydrazone
Acetaldehyde N-formyl-N-methylhydrazone
Acetaldehyde N-methyl-N-formylhydrazone
Acetaldehyde N-methylformylhydrazone
Acetaldehyde, N-formyl-N-methylhydrazone
Acetaldehyde-N-formyl-N-methylhydrazone
Acetaldehyde-N-methyl-N-formylhydrazone
Acetylaldehyde-N-methyl-N-formylhydrazone
Cetaldehyde methylformylhydrazone
Ethylidene gyromitrin
Ethylidenemethyl-Hydrazine carboxaldehyde
Ethylidenemethyl-Hydrazine carboxyaldehyde
Ethylidenemethyl-Hydrazinecarboxaldehyde
Ethylidenemethylhydrazinecarboxaldehyde, 9CI
Formic acid 2-ethylidene-1-methylhydrazide
Formic acid, 2-ethylidene-1-methylhydrazide
Formic acid, ethylidenemethylhydrazide
Hydrazinecarboxaldehyde, ethylidenemethyl- (9CI)
N'-Ethylidene-N-formyl-N-methylhydrazine
N'-Ethylidene-N-methylformic hydrazide
N'-Ethylidene-N-methylformohydrazide
N'-[(1E)-Ethylidene]-N-methylformic hydrazide
N'-[-Ethylidene]-N-methylformic hydrazide
N-Methyl-N-formyl hydrazone of acetaldehyde
N-Methyl-N-formylhydrazone acetaldehyde
Chemical FormulaC4H8N2O
Average Molecular Mass100.119 g/mol
Monoisotopic Mass100.064 g/mol
CAS Registry Number16568-02-8
IUPAC NameN'-[(1E)-ethylidene]-N-methylformohydrazide
Traditional Nameethylidene gyromitrin
SMILES[H]\C(C)=N/N(C)C=O
InChI IdentifierInChI=1S/C4H8N2O/c1-3-5-6(2)4-7/h3-4H,1-2H3/b5-3+
InChI KeyInChIKey=IMAGWKUTFZRWSB-HWKANZROSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as n-alkylated hydrazones. These are organonitrogen compounds containing a hydrazone group that is substituted with an alkyl group. They have the generic structure RNN=C(R')R\" (R= alkyl group; R',R\"= H or organyl group).
KingdomChemical entities
Super ClassOrganic compounds
ClassOrganic nitrogen compounds
Sub ClassOrganonitrogen compounds
Direct ParentN-alkylated hydrazones
Alternative Parents
Substituents
  • N-alkylated hydrazone
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
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
StateLiquid
AppearanceNot Available
Experimental Properties
PropertyValue
Melting Point19.5°C
Boiling Point143 °C, 416°K, 289 °F
SolubilityNot Available
LogPNot Available
Predicted Properties
PropertyValueSource
Water Solubility36.2 mg/mLALOGPS
logP-0.61ALOGPS
logP-0.78ChemAxon
logS-0.44ALOGPS
pKa (Strongest Basic)2.58ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area32.67 Å2ChemAxon
Rotatable Bond Count1ChemAxon
Refractivity27.05 m3·mol-1ChemAxon
Polarizability10.3 Å3ChemAxon
Number of Rings0ChemAxon
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, Positivesplash10-0udi-1900000000-6886f52c8308abf01476View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0zfr-9400000000-1512ed65eadbc59fb19fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-054o-9000000000-4c4b3367f2af862207dbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-9000000000-31d6770e020842c1618bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0595-9000000000-e013bb93be9ce728ea13View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-4f0872f655ea8b457844View in MoNA
Toxicity Profile
Route of ExposureOral, dermal, inhalation, and parenteral (contaminated drugs). (1)
Mechanism of ToxicityThe toxicity is caused by the conversion of the hydrazine (gyromitrin) to a hydrazine metabolite intermediate monomethylhydrazine. This occurs when gyromitrin begins to be metabolized and it undergoes hydrolysis. The necrosis and steatosis are caused by monomethylhydrazine. (3)
MetabolismGyromitrin is converted to a hydrazine metabolite intermediate monomethylhydrazine. This occurs when gyromitrin begins to be metabolized and it undergoes hydrolysis. (3)
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)3, not classifiable as to its carcinogenicity to humans. (4)
Uses/SourcesGyromitrin is a toxic and possibly carcinogenic chemical present in most members of the fungal genus Gyromitra, most notably the false morel G. esculenta. (3)
Minimum Risk LevelNot Available
Health EffectsConsuming large amounts of gyromitrin, such as are found in untreated false morels, may lead to catastrophic liver failure and death. (3)
SymptomsInitial symptoms of gyromitrin exposure include headache, nausea and dizziness. As gyromitrin is quite volatile, even just the presence of false morels in a poorly ventilated space may be enough to cause these symptoms. (3)
TreatmentNot Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB33952
PubChem Compound ID5365327
ChEMBL IDNot Available
ChemSpider ID19957776
KEGG IDC08305
UniProt IDNot Available
OMIM ID
ChEBI ID5583
BioCyc IDNot Available
CTD IDC005666
Stitch IDGyromitrin
PDB IDNot Available
ACToR IDNot Available
Wikipedia LinkGyromitrin
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
  1. Peraica M, Domijan AM: Contamination of food with mycotoxins and human health. Arh Hig Rada Toksikol. 2001 Mar;52(1):23-35. [11370295 ]
  2. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.
  3. Wikipedia. Gyromitrin. Last Updated 29 May 2009. [Link]
  4. International Agency for Research on Cancer (2014). IARC Monographs on the Evaluation of Carcinogenic Risks to Humans. [Link]
Gene Regulation
Up-Regulated GenesNot Available
Down-Regulated GenesNot Available