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. 2008 Aug 9;64(Pt 9):o1739.
doi: 10.1107/S1600536808025324.

N-(Hydroxymethyl)ibogaine

Raoudha Mezghani Jarraya, Amira Bouaziz, Besma Hamdi, Abdelhamid Ben Salah, Mohamed Damak

N-(Hydroxymethyl)ibogaine

Raoudha Mezghani Jarraya et al. Acta Crystallogr Sect E Struct Rep Online. .

Abstract

16-hydroxy-methyl-12-methoxy-ibogamine), C(21)H(28)N(2)O(2), was prepared by reaction of ibogaine with a formaldehyde-acetic acid solution (pH = 4). The crystal structure of this new product, belonging to the iboga indole family, is stabilized by an inter-molecular O-H⋯N hydrogen bond. The identity of the compound was confirmed by one- and two-dimensional NMR spectroscopic techniques.

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Figures

Fig. 1.
Fig. 1.
Chemical pathway of the formation of the N-hydroxymethylene ibogaine (2).
Fig. 2.
Fig. 2.
ORTEP drawing of the title compound with the atom-labelling scheme. Ellispsoids are drawn at the 30% probability level. H atoms are represented as small spheres of arbitrary radii.
Fig. 3.
Fig. 3.
Partial packing view showing the formation of intermolecular O–H···N hydrogen bonds.
Fig. 4.
Fig. 4.
The crystal paking of the N-hydroxymethylene ibogaine structure along [001].
See this image and copyright information in PMC

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