Oxyacanthine

The crystal structure of the title compound (IUPAC name: 6,6',7-trimethoxy-2,2'-dimethyloxyacanthan-12'-ol), C₃₇H₄₀N₂O₆, consists of helical chains, the principal intrachain interaction being hydrogen bonding between the hydroxyl group and one of the amine N atoms. The molecular structure is analysed in detail and results are compared with those reported previously for structurally related tetrandrine. One heterocycle of the molecule assumes a half-boat conformation while the other exists in a conformation intermediate between a half-boat and a half-chair. By analogy with tetrandrine, one amine N atom is predicted to have unrestricted access to its lone pair, whereas the other should display reduced reactivity in reactions dependent on accessibility to a lone pair.

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