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Names | |||
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IUPAC name
N′-Ethylidene-N-methylformohydrazide
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Other names
Acetaldehyde methylformylhydrazone
Formic acid 2-ethylidene-1-methylhydrazide |
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Identifiers | |||
3D model (Jmol)
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1922396 | |||
ChEBI | |||
ChemSpider | |||
KEGG | |||
MeSH | Gyromitrin | ||
PubChem CID
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Properties | |||
C4H8N2O | |||
Molar mass | 100.12 g/mol | ||
Boiling point | 143 °C (289 °F; 416 K) | ||
Hazards | |||
Main hazards | Toxic | ||
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references | |||
Gyromitrin is a toxin and carcinogen present in several members of the fungal genus Gyromitra, G. esculenta. 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.
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 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.
Gyromitrin is a volatile water-soluble hydrazine compound hydrolyzed in the body into monomethylhydrazine (MMH). Other N-methyl-N-formylhydrazone derivatives have been isolated in subsequent research, although they are present in smaller amounts. These other compounds would also produce monomethylhydrazine when hydrolyzed, although it remains unclear how much each contributes to the false morel's toxicity.