5,7,8,14-Tetrahydro-3,4,10,11-tetramethoxy-6-methyldibenz[c,g]azecin-13(6H)-one

Description

This alkaloid, sometimes referred to as cryptopalmine, occurs in Papaver nudi-cauZe L. and in Argernone rnunita Dur. & Hilg. subsp. rotunda. When crystallized from Me2CO it forms clusters of colourless crystals. It furnishes a crystalline hydriodide, m.p. 176-7°C (dec.) and a methiodide, m.p. 192-4°C. The struc_x0002_ture has been deduced from the mass spectrum and confirmed by synthesis.

Definition

ChEBI: Muramine is a dibenzazecine alkaloid that is 5,7,8,14-tetrahydrodibenzo[c,g]azecin-13(6H)-one substituted by a methyl group at position 6 and by methoxy groups at positions 3, 4, 10, and 11. It has a role as a plant metabolite. It is a dibenzazecine alkaloid, a tertiary amino compound and an aromatic ether.

References

Boit, Flentje., Naturwiss., 47, 180 (1960)
Preininger et aZ., PZanta Med., 10, 124 (1962)
Mass spectrum: Cross et aZ., Collect. Czech. Chern. Cornrnun., 30, 1335 (1965)
Synthesis: Haworth, Koepfli, Perkin., 1. Chern. Soc., 2261 (1927)
Giacopello, Deulofeu., Tetrahedron Lett., 2859 (1966)