Ibogaine
Structural Formula Vector Image
Title: Ibogaine
CAS Registry Number: 83-74-9
CAS Name: 12-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 of the iboga group. Isoln from root (1.27%), rootbark (2 to 6%), stems (1.95%) and leaves (0.35%) of the shrub Tabernanthe iboga Baill., Apocynaceae, found in Africa: Dybowski, Landrin, Compt. Rend. 133, 748 (1901); Haller, Heckel, ibid. 850, 1236; from other Apocynaceae: H. Achenbach, B. Raffelsberger, Z. Naturforsch. 35B, 219, 885 (1980); N. Ghorbel et al., J. Nat. Prod. 44, 717 (1981); T. Mulamba et al., ibid. 184; B. Richard et al., ibid. 46, 283 (1983). Purification: Schlittler et al., Helv. Chim. Acta 36, 1341 (1953). Revised extraction procedure: Dickel et al., J. Am. Chem. Soc. 80, 123 (1958). Review of early isolation work: Lebeau, Janot, Traité de Pharmacie Chimique vol. 4 (Masson et Cie., Paris, 1956) pp 2982-2988. Structure: Bartlett et al., J. Am. Chem. Soc. 80, 126 (1958). Mass spectrum: Biemann, Friedmann-Spiteller, ibid. 83, 4805 (1961). Synthesis: Büchi et al., ibid. 88, 3099 (1966); Rosenmund et al., Ber. 108, 1871 (1975). Derivs: Taylor, US 2877229 (1959 to Ciba). Absolute configuration: K. Blàha et al., Tetrahedron Lett. 1972, 2763. Interatomic distances similar to those of serotonin: J. M. Kelley, R. H. Adamson, Pharmacology 10, 28 (1973). NMR spectrum: E. Wenkert et al., Helv. Chim. Acta 59, 2437 (1976). Determn in biological fluids: E. Bertol et al., J. Chromatogr. 117, 239 (1976). Iboga extracts said to be used by African natives while stalking game, to enable them to remain motionless for as long as 2 days while retaining mental alertness. Neuropharmacological studies: Schneider, Sigg, Ann. N.Y. Acad. Sci. 66, 765 (1957); S. Gershon, W. J. Lang, Arch. Int. Pharmacodyn. Ther. 135, 31 (1962). Cardiovascular effects: J. A. Schneider, R. K. Rinehart, ibid. 110, 92 (1957). Serotonergic properties: R. S. Sloviter et al., J. Pharmacol. Exp. Ther. 214, 231 (1980). Experimental use in treatment of heroin addiction: H. S. Lotsof, US 4499096 (1985). Reviews: W. I. Taylor, "The Iboga and Voacanga Alkaloids" in The Alkaloids, Chemistry and Physiology Vol. 8, R. H. F. Manske, Ed. (Academic Press, New York, 1965) p 203-235, idem, ibid. Vol. 11 (1968), pp 79-98.
Properties: Prismatic needles from abs ethanol, mp 152-153°. Sublimes0.01 150°. [a]D20 -53° (in 95% ethanol). pKa 8.1 in 80% methylcellosolve. uv max (methanol): 226, 298 nm (log e 4.39, 3.93). Sol in ethanol, ether, chloroform, acetone, benzene. Practically insol in water.
Melting point: mp 152-153°
pKa: pKa 8.1 in 80% methylcellosolve
Optical Rotation: [a]D20 -53° (in 95% ethanol)
Absorption maximum: uv max (methanol): 226, 298 nm (log e 4.39, 3.93)
 
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. Dec 299-300°. [a]D25 -63° (ethanol); [a]D25 -49° (H2O). Soluble in water, methanol, ethanol. Slightly sol in acetone, chloroform. Practically insol in ether.
Optical Rotation: [a]D25 -63° (ethanol); [a]D25 -49° (H2O)
 
NOTE: This is a controlled substance (hallucinogen): 21 CFR, 1308.11.

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