Methylazoxymethanol

Last updated
Methylazoxymethanol
Methylazoxymethanol.svg
Names
IUPAC name
(Z)-hydroxymethylimino-methyl-oxidoazanium[ citation needed ]
Preferred IUPAC name
[(Z)-methyl-ONN-azoxy]methanol
Other names
MAM
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
KEGG
PubChem CID
UNII
  • InChI=1S/C2H6N2O2/c1-4(6)3-2-5/h5H,2H2,1H3/b4-3-
    Key: BJNBRIBHKLJMAG-ARJAWSKDSA-N
  • C[N+](=NCO)[O-]
Properties
C2H6N2O2
Molar mass 90.082
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Methylazoxymethanol, MAM, is a carcinogen which reduces DNA synthesis. [1] Its derivatives include methylazoxymethanol acetate and cycasin, which they are found in cycad.

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Mam or MAM may refer to:

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<span class="mw-page-title-main">Methylazoxymethanol acetate</span> Chemical compound

Methylazoxymethanol acetate, MAM, is a neurotoxin which reduces DNA synthesis used in making animal models of neurological diseases including schizophrenia and epilepsy. MAM is found in cycad seeds, and causes zamia staggers. It selectively targets neuroblasts in the central nervous system. In rats, administration of MAM affects structures in the brain which are developing most quickly. It is an acetate of methylazoxymethanol.

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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.

The molecular formula C2H6N2O2 (molar mass: 90.08 g/mol) may refer to:

References

  1. "Methylazoxymethanol – Compound Summary". PubChem . National Center for Biotechnology Information . Retrieved 9 February 2019.