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Cycasin
Chemical compound / From Wikipedia, the free encyclopedia
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Cycasin is a carcinogenic and neurotoxic glucoside found in cycads such as Cycas revoluta and Zamia pumila. Symptoms of poisoning include vomiting, diarrhea, weakness, seizures, and hepatotoxicity. In metabolic conditions, cycasin is hydrolyzed into glucose and methylazoxymethanol (MAM), the latter of which dissociates into formaldehyde and diazomethane.[3]
Quick Facts Names, Identifiers ...
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Names | |
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IUPAC name
(Z)-1-[(β-D-Glucopyranosyloxy)methyl]-2-methyldiazene 2-oxide | |
Systematic IUPAC name
(Z)-1-Methyl-2-({[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)diazene 1-oxide | |
Other names
β-D-Glucosyloxyazoxymethane; Methylazoxymethanol β-D-glucoside; Cycas revoluta glucoside; [(Z)-Methyl-ONN-azoxy]methyl β-D-glucopyranoside[1] | |
Identifiers | |
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MeSH | D003492 |
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Properties | |
C8H16N2O7 | |
Molar mass | 252.223 g·mol−1 |
56.6 g/L[2] | |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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It induces hepatotoxicity and Zamia staggers, a fatal nervous disease affecting cattle resulting from browsing on the leaves or other parts of cycads.[4]