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Topic summary

Gyromitrin

Gyromitrin
Names IUPAC name
N′-Ethylidene-N-methylformohydrazide
Other names
Acetaldehyde methylformylhydrazone
Formic acid 2-ethylidene-1-methylhydrazide
Identifiers
3D model (JSmol)
1922396 ChEBI
ChemSpider
KEGG
MeSHGyromitrin
UNII
  • InChI=1S/C4H8N2O/c1-3-5-6(2)4-7/h3-4H,1-2H3
    Key: IMAGWKUTFZRWSB-UHFFFAOYSA-N
  • CC=NN(C)C=O
Properties C4H8N2OMolar mass100.121 g·mol Boiling point143 °C (289 °F; 416 K) Hazards Occupational safety and health (OHS/OSH):
Main hazards
highly toxic and reactive liquid
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Gyromitrin is a toxin and carcinogen present in several members of the fungalgenusGyromitra, like G. esculenta. Its formula is C4H8N2O. It is unstable and is easily hydrolyzed to the toxic compound monomethylhydrazineCH3NHNH2. Monomethylhydrazine acts on the central nervous system and interferes with the normal use and function of vitamin B6. Poisoning results in nausea, stomach cramps, and diarrhea, while severe poisoning can result in convulsions, jaundice, or even coma or death. Exposure to monomethylhydrazine has been shown to be carcinogenic in small mammals.

Wikipedia source