Me. Tate et al., CRYSTAL AND MOLECULAR-STRUCTURE AND BIOLOGICAL-ACTIVITY OF (Z)-(BENZOYLOXYMETHYL-NNO-AZOXY)METHANE, Australian Journal of Chemistry, 50(7), 1997, pp. 771-773
Characterization of (benzoyloxymethyl-NNO-azoxy)methane, from benzoyla
tion of the cycasin aglycone methylazoxymethanol, commonly referred to
as MAM, is reported. Crystal structure analysis shows that the azoxy
substituents have the Z configuration. Crystals are monoclinic, space
group P2(1)/c, a 7.436(2), b 8.771(2), c 14.640(1) Angstrom, beta 90.7
3(1)degrees, Z 4; the structure was refined to final R 0.048 by using
1171 reflections with I > 3.0 sigma(I). Subcutaneous injection of (Z)-
(benzoyloxymethyl-NNO-azoxy) methane in mice showed liver changes typi
cal of the corresponding MAM acetate-induced hepatotoxicity. This perm
its correlation of hepatotoxic effects with the Z configuration of the
aglycone. Histological examination of the brain and spinal cord revea
led no significant changes at a dosage of 52.6 mg/kg.