Gyromitrin

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IUPACName = "N"-(ethylideneamino)-"N"-methyl-
formamide
OtherNames = Acetaldehyde methylformylhydrazone formic acid 2-ethylidene-1-methylhydrazide Acetaldehyde methylformylhydrazone
Formula = C₄H₈N₂O
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CASNo = 16568-02-8
EINECS = | PubChem = 9548611
SMILES = C/C=N/N(C)C=O
InChI = 1/C4H8N2O/c1-3-5-6(2)4-7/h3-4H,1-2H3/b5-3+| RTECS =
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ChEBI = 5583
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MolarMass =100.119 g/mol
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MainHazards = Toxic
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Gyromitrin is a toxic and possibly carcinogenic chemical present in most members of the mushroom genus "Gyromitra", most notably the False Morel ("Gyromitra esculenta"). In the body it is metabolized to monomethylhydrazine (MMH) " "See: " [http://books.google.com/books?id=fZtgamJXk70C&pg=RA1-PA285&lpg=RA1-PA285&dq=gyromitrin+mechanism&source=web&ots=rYXFSlSGeX&sig=m5I6iVgpXIzrt96kcZGrukr4JEU#PRA1-PA286,M1]

Mechanism of Toxicity

The toxicity is caused by the conversion of the hydrazine (gyromitrin) to a hydrazine metabolite intermediate monomethylhydrazine. This occurs when begins to be metabolized and it undergoes hydrolysis. The necrosis and steatosis are caused by monomethylhydrazine.

Removal of Gyromitrin

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. [http://www.uaf.edu/snras/afes/pubs/misc/MP_05_07.pdf Page 3]

References

External links

* [http://botit.botany.wisc.edu/toms_fungi/may2002.html "Gyromitra esculenta", one of the false morels"]
* [http://www.dlc.fi/~marianna/gourmet/morel.htm#instrc Official Finnish instructions for the processing of false morels]
* [http://books.google.com/books?id=fZtgamJXk70C&pg=RA1-PA285&lpg=RA1-PA285&dq=gyromitrin+mechanism&source=web&ots=rYXFSlSGeX&sig=m5I6iVgpXIzrt96kcZGrukr4JEU#PRA1-PA286,M1 Hepatotoxicity: The Adverse Effects of Drugs and Other Chemicals on the Liver]