Cycasin

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
Identifiers
CAS Number	14901-08-7 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:CHEBI:17074;
ChemSpider	4573631;
KEGG	C01418;
MeSH	D003492
PubChem CID	5459896;
UNII	9H51HL0E1D ;
CompTox Dashboard (EPA)	DTXSID2057574 ;
	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
	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.

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