Gyromitrin

Gyromitrin
Wireframe model of gyromitrin
Wireframe model of gyromitrin
Ball and stick model of gyromitrin
Ball and stick model of 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
MeSH Gyromitrin
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
C4H8N2O
Molar mass 100.121 g·mol−1
Boiling point 143 °C (289 °F; 416 K)
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
Toxic
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 fungal genus Gyromitra, like G. esculenta. Its formula is C4H8N2O. It is unstable and is easily hydrolyzed to the toxic compound monomethylhydrazine CH3NHNH2. 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.