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Cycasin information


Cycasin
Chemical structure of cycasin
Names
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
CAS Number
  • 14901-08-7 checkY
3D model (JSmol)
  • Interactive image
ChEBI
  • CHEBI:CHEBI:17074
ChemSpider
  • 4573631
KEGG
  • C01418
MeSH D003492
PubChem CID
  • 5459896
UNII
  • 9H51HL0E1D checkY
CompTox Dashboard (EPA)
  • DTXSID2057574 Edit this at Wikidata
InChI
  • InChI=1S/C8H16N2O7/c1-10(15)9-3-16-8-7(14)6(13)5(12)4(2-11)17-8/h4-8,11-14H,2-3H2,1H3/b10-9-/t4-,5-,6+,7-,8-/m1/s1
    Key: YHLRMABUJXBLCK-LBCXAKKBSA-N
  • InChI=1/C8H16N2O7/c1-10(15)9-3-16-8-7(14)6(13)5(12)4(2-11)17-8/h4-8,11-14H,2-3H2,1H3/b10-9-/t4-,5-,6+,7-,8-/m1/s1
    Key: YHLRMABUJXBLCK-LBCXAKKBSA
SMILES
  • [O-]/[N+](=N/CO[C@@H]1O[C@@H]([C@@H](O)[C@H](O)[C@H]1O)CO)C
Properties
Chemical formula
C8H16N2O7
Molar mass 252.223 g·mol−1
Solubility in water
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).
Infobox references

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]

It induces hepatotoxicity and Zamia staggers, a fatal nervous disease affecting cattle resulting from browsing on the leaves or other parts of cycads.[4]

  1. ^ b-D-Glucosyloxyazoxymethane, ChemSpider
  2. ^ "Showing Compound Cycasin (FDB018287) - FooDB".
  3. ^ Laqueur, G. L.; Spatz, M. (November 1968). "Toxicology of Cycasin". Cancer Research. 28 (11): 2262–2267. PMID 4881504.
  4. ^ Cite error: The named reference Zam was invoked but never defined (see the help page).

and 21 Related for: Cycasin information

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Cycasin

Last Update:

Cycasin is a carcinogenic and neurotoxic glucoside found in cycads such as Cycas revoluta and Zamia pumila. Symptoms of poisoning include vomiting, diarrhea...

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Cycas revoluta

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contains cycasin toxin and should not be eaten as it is possible for cycasin toxin to survive the most vigorous of repeated washings. Cycasin toxin can...

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Sago

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are highly poisonous: most parts of the plant contain the neurotoxins cycasin and BMAA. Consumption of cycad seeds has been implicated in the outbreak...

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Methylazoxymethanol

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DNA synthesis. Its derivatives include methylazoxymethanol acetate and cycasin, which they are found in cycad. "Methylazoxymethanol – Compound Summary"...

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Zamia furfuracea

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erect in full sun, horizontal in shade. All parts of the plant contain Cycasin and an unknown nervous system toxin which are poisonous to animals, including...

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Zamia integrifolia

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water for several hours to remove the rest of the water-soluble toxin cycasin. The resulting paste was then left to ferment before being dried into a...

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IARC group 2B

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diethanolamine condensate para-Cresidine Crotonaldehyde Cumene Cupferron Cycasin Dacarbazine Dantron (Chrysazin, 1,8-Dihydroxyanthraquinone) Daunomycin...

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Zamia pumila

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for cattle ranching. This plant is poisonous, producing a toxin called cycasin that affects the gastrointestinal tract and nervous system. The toxin can...

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Hepatotoxicity

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products. Examples include: Ackee fruit, Bajiaolian, Camphor, Copaltra, Cycasin, Garcinia, Kava leaves, pyrrolizidine alkaloids, Horse chestnut leaves...

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Taenaris

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with blue-black "pupils". Due to their larval diet consisting of toxic cycasin-rich foodplants, many members of genus are involved within Müllerian mimicry...

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Encephalartos ghellinckii

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The seeds are poisonous, containing the azoxyglycosides macrozamin and cycasin, and these are also present in the flesh, roots, stems and leaves, though...

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Zamiaceae

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of the Zamiaceae are poisonous, producing poisonous glycosides known as cycasins. The former family Stangeriaceae (which contained Bowenia and Stangeria)...

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Eumaeus atala

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caterpillar feeds on cycads that contain a toxic secondary plant chemical (cycasin) that it retains in its body for life. Birds, lizards, and other animals...

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California Proposition 65 list of chemicals

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p-Cresidine 120-71-8 Cumene 98-82-8 Cupferron 135-20-6 Cyanazine 21725-46-2 Cycasin 14901-08-7 Cycloate 1134-23-2 Cycloheximide 66-81-9 Cyclopenta[cd]pyrene...

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Macrozamia fraseri

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of the past. Macrozamia fraseri contains poisonous glycosides known as cycasins. Hill, K.D. (2010). "Macrozamia fraseri". IUCN Red List of Threatened Species...

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Zamia staggers

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because of the degeneration of the spinal cord. It is caused by the toxins cycasin and macrozamin, β-glycosides (the sugars of which are glucose and primeverose...

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Macrozamia riedlei

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toxins contained in the cone and other parts of the plant, macrozamin and cycasin, are produced in coralloid roots by nitrogen-fixing cyanobacteria. The...

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Macrozamia miquelii

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the cycad having a higher concentration of azoxyglycosides, including cycasin and macrozamin, than other parts of the plant. Other toxins identified...

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Hally Jolivette Sax

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Sax) The cytogenetics of generic hybrids of Sorbus (1947, with Karl Sax) Cycasin: Radiomimetic effects (1965, with Karl Sax and H.J. Teas) Radiomimetic...

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Macrozamia dyeri

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vulpecula, a common possum known locally as quumarl. The toxins macrozamin and cycasin are produced by cyanobacteria engaged in nitrogen fixing at their coralloid...

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Macrozamia heteromera

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Castillo-Guevara, Citlalli; Rico-Gray, Victor (2007). "The Role of Macrozamin and Cycasin in Cycads (Cycadales) as Antiherbivore Defenses". Journal of the Torrey...

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