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Gyromitrin information


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
CAS Number
  • 16568-02-8 checkY
3D model (JSmol)
  • Interactive image
Beilstein Reference
1922396
ChEBI
  • CHEBI:5583
ChemSpider
  • 25985
  • 7827534 (1E)
  • 19957776 (1Z)
KEGG
  • C08305
MeSH Gyromitrin
PubChem CID
  • 27932
  • 9548611 (1E)
  • 5365327 (1Z)
UNII
  • S9J72G0T46 checkY
CompTox Dashboard (EPA)
  • DTXSID50872971 Edit this at Wikidata
InChI
  • InChI=1S/C4H8N2O/c1-3-5-6(2)4-7/h3-4H,1-2H3
    Key: IMAGWKUTFZRWSB-UHFFFAOYSA-N
SMILES
  • CC=NN(C)C=O
Properties
Chemical formula
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).
Infobox references

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.

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Gyromitrin

Last Update:

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...

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Gyromitra esculenta

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traces of mycotoxins. When consumed, the principal active mycotoxin, gyromitrin, is hydrolyzed into the toxic compound monomethylhydrazine, which affects...

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False morel

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inadequately cooked, or over several days in a row. Some species contain gyromitrin, a toxic and carcinogenic organic compound, which is hydrolyzed in the...

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Monomethylhydrazine

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(Gyromitra esculenta). In these cases, MMH is formed by the hydrolysis of gyromitrin. Monomethylhydrazine is considered to be a possible occupational carcinogen...

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Mushroom poisoning

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particular Clitocybe dealbata, and some red-pored Boletes. Gyromitrin: Stomach acids convert gyromitrin to monomethylhydrazine (MMH). It affects multiple body...

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Hydrazines

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rocket fuel. gyromitrin and agaritine are hydrazine derivatives found in the commercially produced mushroom species Agaricus bisporus. Gyromitrin is metabolized...

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Hydrazine

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anammox (Brocadia anammoxidans). The false morel produces the poison gyromitrin which is an organic derivative of hydrazine that is converted to monomethylhydrazine...

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Edible mushroom

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mycologists do not recommend it. Raw Gyromitra are toxic due to the presence of gyromitrin, and it is not known whether all of the toxin can be removed by parboiling...

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Gyromitra

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Gyromitra are highly poisonous when eaten raw due to the presence of gyromitrin, although some are edible when cooked and Gyromitra spp. are sought after...

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Paragyromitra infula

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The species is considered inedible as it contains the toxic compound gyromitrin which, when metabolized by the body, is converted into monomethylhydrazine...

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Discina gigas

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mushrooms. It contains small quantities of hydrazines; its content in gyromitrin was scientifically assessed by Viernstein et al. [Botanical identification...

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Helvella solitaria

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recommended[according to whom?] as similar species in the Helvellaceae contain the toxin gyromitrin.[citation needed] "GSD Species Synonymy: Helvella solitaria P. Karst"...

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Agaritine

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consuming mushrooms. Agaritine gamma-glutamyltransferase Genotoxicity Gyromitrin Monomethylhydrazine "Agaritine". PubChem, US National Library of Medicine...

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Hydrazone

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an illustrative hydrazone Carbonyl cyanide m-chlorophenyl hydrazone Gyromitrin (acetaldehyde methylformylhydrazone), a toxin Dihydralazine, an antihypertensive...

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Verpa bohemica

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species Gyromitra esculenta. The responsible toxin in G. esculenta is gyromitrin; it was suspected that V. bohemica may be able to synthesize low levels...

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List of deadly fungus species

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liver Indonesia Gyromitra esculenta (Pers. ex Pers.) Fr. false morel gyromitrin and monomethylhydrazine multiple (depletes PLP stores) Coniferous woodlands...

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Morchella

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inadequately cooked, or over several days in a row. False morels contain gyromitrin, an organic carcinogenic poison, hydrolyzed in the body into monomethylhydrazine...

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IARC group 3

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(Frusemide) Gemfibrozil Glycidyl oleate Glycidyl stearate Guinea Green B Gyromitrin Haematite HC Blue No. 2 HC Red No. 3 HC Yellow No. 4 Hepatitis D virus...

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Helvella latispora

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recommended as similar species in the family Helvellaceae contain the toxin gyromitrin. Jordan, Michael (2004). The Encyclopedia of Fungi of Britain and Europe...

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List of poisonous fungus species

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circinans gyromitrin and monomethylhydrazine North America, Europe and Asia Morchella spp. Cantharellus spp. Gyromitra perlata Pig's ears gyromitrin and monomethylhydrazine...

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Paragyromitra ambigua

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not known with certainty, and it is not recommended for consumption. Gyromitrin, a toxic chemical found in Gyromitra fungi Morchella, the true morels...

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California Proposition 65 list of chemicals

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Goldenseal root powder – Goserelin acetate 65807-02-5 Griseofulvin 126-07-8 Gyromitrin (Acetaldehyde methylformylhydrazone) 16568-02-8 Halazepam 23092-17-3 Halobetasol...

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Dissingia leucomelaena

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recommended as similar species in the family Helvellaceae contain the toxin gyromitrin. Tylutki EE (1979). Mushrooms of Idaho and the Pacific Northwest. Moscow:...

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Gyromitra caroliniana

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confusion with other toxic Gyromitra species that contain the compound gyromitrin. When boiled in water, or digested in the body, this compound is readily...

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Helvella elastica

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recommended as similar species in the family Helvellaceae contain the toxin gyromitrin. A 2005 Korean study investigated the ability of extracts from 67 different...

Word Count : 705

Helvella corium

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recommended as similar species in the family Helvellaceae contain the toxin gyromitrin.[citation needed] Jordan M. (2004). The Encyclopedia of Fungi of Britain...

Word Count : 576

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