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gyromitrin
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gyromitrin

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Also known as N-(ethylideneamino)-N-methylformamide

Gyromitrin is a toxin and carcinogen present in several members of the fungal genus Gyromitra, like G. esculenta. Its formula is . It is unstable and is easily hydrolyzed to the toxic compound monomethylhydrazine . 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.

Wikidata facts

Mass
100.064
Show 3 more facts
chemical formula
C₄H₈N₂O
canonical SMILES
CC=NN(C)C=O
Commons category
Gyromitrin
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~14 min read

Article

13 sections
Contents
  • History
  • Mechanism of toxicity
  • Occurrence and removal
  • Detection
  • Identification
  • Poisoning
  • Symptoms
  • Treatment
  • Toxicity controversy
  • Carcinogenicity
  • References
  • Books cited
  • External links

Gyromitrin is a toxin and carcinogen present in several members of the fungal genus Gyromitra, like G. esculenta. Its formula is . It is unstable and is easily hydrolyzed to the toxic compound monomethylhydrazine . 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.

==History== Poisonings related to consumption of the false morel Gyromitra esculenta, a highly regarded fungus eaten mainly in Finland and by some in parts of Europe and North America, had been reported for at least a hundred years. Experts speculated the reaction was more of an allergic one specific to the consumer, or a misidentification, rather than innate toxicity of the fungus, due to the wide range in effects seen. Some would suffer severely or perish while others exhibited no symptoms after eating similar amounts of mushrooms from the same dish. Yet others would be poisoned after previously eating the fungus for many years without ill-effects. In 1885, Böhm and Külz described helvellic acid, an oily substance they believed to be responsible for the toxicity of the fungus. The identity of the toxic constituents of Gyromitra species eluded researchers until 1968, when N-methyl-N-formylhydrazone was isolated by German scientists List and Luft and named gyromitrin. Each kilogram of fresh false morel had between 1.2 and 1.6 grams of the compound.

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