Structure via PubChem · Public domain (PubChem)
cycasin
Sign in to saveCycasin 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.
Chemical data
- Formula
- C8H16N2O7
- Molecular weight
- 252.22 g/mol
- IUPAC name
- (E)-methyl-oxido-[[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethylimino]azanium
- SMILES
- C/[N+](=N\CO[C@H]1[C@@H]([C@H]([C@@H]([C@H](O1)CO)O)O)O)/[O-]
- InChIKey
- YHLRMABUJXBLCK-IRCVIWNGSA-N
- XLogP
- -2.6
- Polar surface area
- 140 Ų
- H-bond donors
- 4
- H-bond acceptors
- 8
- Formal charge
- 0
via PubChem
Research
171 papers- Cycasin.IARC monographs on the evaluation of the carcinogenic risk of chemicals to man · 1976
- Toxicology of cycasin.Food and cosmetics toxicology · 1968
- Cycasin and its mutagenic metabolites.Mutation research · 1983
- Toxicology of cycasin.Cancer research · 1968
- Cycasin derivative: a potential embryotoxic component of Atractylodes macrocephala rhizome for limb malformation.Toxicology research · 2024
via PubMed
Wikidata facts
- Mass
- 252.095750852
Show 5 more facts
- chemical formula
- C₈H₁₆N₂O₇
- subject has role
- neurotoxin
- isomeric SMILES
- C/[N+](=N/CO[C@H]1[C@@H]([C@H]([C@@H]([C@H](O1)CO)O)O)O)/[O-]
- canonical SMILES
- [O-][N+](=NCOC1OC(CO)C(O)C(O)C1O)C
- found in taxon
- Cycas media
via Wikidata · CC0
~6 min read
Encyclopedic overview
10 sectionsContents
- Sources
- Ecological significance
- Presence in sago
- Structure
- Toxicity
- Symptoms
- Zamia staggers
- Suspected association with Lytico-bodig disease
- See also
- References
{{Chembox | ImageFile = Cycasin.png | ImageSize = 200px | ImageAlt = Chemical structure of cycasin | ImageClass = skin-invert-image | IUPACName = (Z)-1-[(β-D-Glucopyranosyloxy)methyl]-2-methyldiazene 2-oxide | SystematicName = (Z)-1-Methyl-2-({[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)diazene 1-oxide | OtherNames = β-D-Glucosyloxyazoxymethane; Methylazoxymethanol β-D-glucoside; Cycas revoluta glucoside; [(Z)-Methyl-ONN-azoxy]methyl β-D-glucopyranoside |Section1= |Section2= |Section3= }} 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.
It induces hepatotoxicity and Zamia staggers, a fatal nervous disease affecting cattle resulting from browsing on the leaves or other parts of cycads.
Excerpted from Wikipedia’s “cycasin” article, available under the CC BY-SA 4.0 licence.