Gyromitrin

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Gyromitrin

IUPAC name	N-(ethylideneamino)-N-methyl- formamide
Other names	Acetaldehyde methylformylhydrazone formic acid 2-ethylidene-1-methylhydrazide Acetaldehyde methylformylhydrazone
Molecular formula	C₄H₈N₂O
Identifiers
CAS number	[16568-02-8]
PubChem	9548611
KEGG	C08305
ChEBI	5583
SMILES	[H]C(=O)N(C)\N=C\C
InChI	InChI=1/C4H8N2O/c1-3-5-6(2)4-7/h3-4H,1-2H3/b5-3+
Properties
Molar mass	100.119 g/mol
Boiling point	143
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox disclaimer and references

Gyromitrin is a toxic and possibly carcinogenic chemical present in most members of the False Morel genus of mushrooms. In the body it is metabolized to monomethylhydrazine (MMH).

Gyromitrin is volatile and water soluble, and can be mostly removed from the mushrooms by cutting them to small pieces and repeatedly boiling them in copious water under good ventilation. While most people experience no ill effects from ingesting the remaining small doses of gyromitrin, some may have a metabolic sensitivity to it and can become seriously ill from eating even properly prepared false morels.

Initial 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. Consuming large amounts of gyromitrin, such as are found in untreated false morels, may lead to catastrophic liver failure and death.

There is some evidence that even small doses of gyromitrin may have a cumulative carcinogenic effect. Thus it may not be advisable to consume even properly treated false morels too frequently.