Acetaldehyde methylformylhydrazone
Basic information
- CAS
16568-02-8- Standard SMILES
CC=NN(C)C=O- InChIKey
IMAGWKUTFZRWSB-UHFFFAOYSA-N- Molecular formula
- C4H8N2O
- Average molar mass
- 100.12 g/mol
- Monoisotopic mass
- 100.06366288
Overview
Gyromitrin 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.
Names & identifiers
- Preferred name
- Acetaldehyde methylformylhydrazone
- IUPAC
- N-(ethylideneamino)-N-methylformamide
- English name
- gyromitrin
- Molecular formula
- C4H8N2O
- Molecular weight
- 100.12
Names & synonyms
DTXSID0039225Acetaldehyde methylformylhydrazoneRefChem:314233DTXCID20810022orb3141887SCHEMBL2932999RAA56802N-(ethylideneamino)-N-methyl-formamidegyromitrinETHYLENEGYROMITRINMETHYLFORMYLHYDRAZONEEthylidene gyromitrin
Show more names
ACETALDEHYDEMETHYLFORMYLHYDRAZONEFORMICACID,ETHYLIDENEMETHYLHYDRAZIDEACETALDEHYDE-N-METHYL-N-FORMYLHYDRAZONE2-Ethylidene-1-methylhydrazinecarboxaldehyde2-Ethylidene-1-methyl-1-hydrazinecarbaldehydeHydrazinecarboxaldehyde, 2-ethylidene-1-methyl-
Database identifiers
- CAS
16568-02-8- PubChem CID
- 27932
- DTXSID
DTXSID0039225
Properties
Computed structural properties
- XLogP
- -0.3
- Topological polar surface area
- 32.7 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 2
- Rotatable bonds
- 1
- Heavy atoms
- 7
- Formal charge
- 0
- Complexity
- 79.8
Physicochemical properties
- Boiling point
- 187.56 °C · 187.56°C (rough estimate)
- Density
- 1.1275 · 1.1275 (rough estimate)
- refractive index
- 1.488 · 1.4880 (estimate)
- solubility
- Chloroform (Soluble), DMSO (Slightly), Ethyl Acetate (Sparingly)
- form
- Oil
- pka
- 2.36 · 2.36±0.70(Predicted)
- color
- Colourless to Yellow
- Stability
- Light Sensitive
- LogP
- -0.3 · -0.300 (est)
- FDA UNII
- 9 J72G0T46 · S9J72G0T46
- Proposition 65 List
- Gyromitrin
- IARC
- 3 · 3 (Vol. 31, Sup 7) 1987
- EPA Substance Registry System
- Gyromitrin (16568-02-8)
- RIDADR
- 1544 · 1544
- HazardClass
- 6.1 · 6.1(b)
- PackingGroup
- III
- Hazardous Substances Data
- 16568 · 16568-02-8(Hazardous Substances Data)
- Toxicity
- 50 orl-rat: · LD50 orl-rat: 320 mg/kg FCTXAV 15,575,77
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Toxicology
Health EffectsConsuming large amounts of gyromitrin, such as are found in untreated false morels, may lead to catastrophic liver failure and death. (L1013)
Exposure RoutesOral, dermal, inhalation, and parenteral (contaminated drugs). (A3101)
Toxicity Summary
The 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. (L1013)
Signs and 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. (L1013)
Carcinogen Classification3, not classifiable as to its carcinogenicity to humans. (L135)
Safety data
- ridadr
- 1544
- Toxicity
- LD50 orl-rat: 320 mg/kg FCTXAV 15,575,77
- hazard_class
- 6.1(b)
- packing_group
- III
- Hazardous Substances Data
- 16568-02-8(Hazardous Substances Data)
Chemistry & industry
Pharmacology
Metabolism/MetabolitesGyromitrin is converted to a hydrazine metabolite intermediate monomethylhydrazine. This occurs when gyromitrin begins to be metabolized and it undergoes hydrolysis. (L1013)
Uses & manufacturing
UsesGyromitrin is a toxic and possibly carcinogenic chemical present in most members of the fungal genus Gyromitra, most notably the false morel G. esculenta. (L1013)
Applications
UsesGyromitrin is hepatotoxic and carcinogenic compound that is found in G. esculenta and few other mushrooms, which has resulted in severe poisonings and even deaths in human.
Additional notes
DefinitionChEBI: Gyromitrin is a hydrazone and an aldehyde. It is functionally related to an acetaldehyde hydrazone.
Related reactions
0 records
No reaction records under the current filter.
Compound notes
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