Tabernanthine
Title: Tabernanthine
CAS Registry Number: 83-94-3
CAS Name: 13-Methoxyibogamine
Molecular Formula: C20H26N2O
Molecular Weight: 310.43
Percent Composition: C 77.38%, H 8.44%, N 9.02%, O 5.15%
Literature References: Indole alkaloid isolated from root of Tabernanthe iboga Baill., Apocynaceae: Delourme-Houdé, Ann. Pharm. Fr. 4, 30 (1946); Dickel et al., J. Am. Chem. Soc. 80, 123 (1958). Also in Tabernaemontana and Stemmadenia spp.; usually found in ibogaine mother liquors: Walls et al., Tetrahedron 2, 173 (1958). Isoln from genus Conopharingia, Apocynaceae: Renner, Prins, US 3008954 (1961 to Geigy). Structure: Bartlett et al., J. Am. Chem. Soc. 80, 126 (1958). Mass spectrum: Biemann, Friedmann-Spiteller, ibid. 83, 4805 (1961). Derivs: Taylor, US 2877229 (1959 to Ciba). Interaction with benzodiazepine receptors: J.-H. Trouvin et al., Eur. J. Pharmacol. 140, 303 (1987).
Properties: Needles or shiny leaflets from ethanol, mp 213.5-215°. Sublimes at 160° (0.005 mm pressure). [a]D20 -40° (acetone). pKa 6.04 in 80% methylcellosolve. uv max (ethanol): 228, 271, 299 nm (log e 4.53, 3.64, 3.77). Sol in alcohol, benzene, ether, chloroform. Practically insol in water.
Melting point: mp 213.5-215°
pKa: pKa 6.04 in 80% methylcellosolve
Optical Rotation: [a]D20 -40° (acetone)
Absorption maximum: uv max (ethanol): 228, 271, 299 nm (log e 4.53, 3.64, 3.77)
 
Derivative Type: Hydrochloride
Molecular Formula: C20H26N2O.HCl
Molecular Weight: 346.89
Percent Composition: C 69.25%, H 7.85%, N 8.08%, O 4.61%, Cl 10.22%
Properties: Crystals from water, dec 275-277°. [a]D25 -66° (methanol, Dickel, loc. cit.); mp 210°, [a]D20 -76.5° (methanol, Delourme-Houdé). Sol in water. More sol in chloroform than ibogaine hydrochloride.
Melting point: mp 210°
Optical Rotation: [a]D25 -66° (methanol, Dickel, loc. cit.); [a]D20 -76.5° (methanol, Delourme-Houdé)

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