IBOGAINE

Description

This indole alkaloid occurs in the root of Tabernanthe iboga Baill. It was first examined in detail by Raymond-Hamet who assigned to it the empirical formula C19H24(26)ON2, now altered to that given above. The base forms colourless crystals from EtOH and is laevorotatory with [Q1D - 53° (EtOH). It is insoluble in Et20, slightly so in Me2CO or CHC1 3 but dissolves freely in MeOH, EtOH or H20. The alkaloid yields a hydrochloride, m.p. 299°C (dec.); lQlhs - 67° (MeOH) or - 37.3° (H20). It contains one methoxyl group and gives the typical indole reactions. On distillation with Zn dust or soda-lime it furnishes products which are indole derivatives with the ~-position free.
In a manner similar to that of cocaine, the alkaloid potentiates the pressor action of adrenaline and abolishes the sino-carotid reflexes. Unlike cocaine, however, it also augments the action of tyramine and that of dl-ephedrine to a slight extent. Vincent and Sero have reported that it inhibits the action of serum cholinesterase.

Description

Ibogaine is an indole alkaloid that occurs in West African shrubs in the Apocynaceae family, including?Tabernanthe iboga, for which it is named. Iboga root has long been used in the Bwiti rituals of peoples in Gabon, Cameroon, and the Republic of the Congo.
Ibogaine is hallucinogenic and neurotoxic, but it has shown some success in reducing withdrawal effects from drugs of abuse, such as alcohol, nicotine, and methamphetamine. Some governments, fearing abuse, have banned it outright. The US Food and Drug Administration classifies it as a Schedule I controlled substance, but it has permitted research on ibogaine for combating addiction.

Definition

ChEBI: Ibogaine is an organic heteropentacyclic compound that is ibogamine in which the indole hydrogen para to the indole nitrogen has been replaced by a methoxy group. It has a role as a plant metabolite, an inhibitor, a hallucinogen and a oneirogen. It is a monoterpenoid indole alkaloid, an organic heteropentacyclic compound and an aromatic ether. It is functionally related to an ibogamine. It is a conjugate base of an ibogaine(1+).

Purification Methods

Crystallise it from EtOH or aqueous EtOH and sublime it at 150o/0.01mm. It is soluble in organic solvents but insoluble in H2O. The hydrochloride, m 299-300o(dec), is soluble in H2O and alcohols. [Büchi et al. J Am Chem Soc 88 3099 1866, Rosenmund Chem Ber 108 1871 1975, Beilstein 23 III/IV 2742.]

References

Raymond-Hamet., Bull. Soc. Chirn. Fr., 9,620 (1942)
Delourme-Houde., Chern. Abstr., 41, 1390 (1947)
Bartlett, Dickel, Taylor.,J. Arner. Chern. Soc., 80, 126 (1958)
Arai, Coppola, Jeffery., Acta Cryst., 13, 553 (1960)
Shamma, Soyster., Experientia, 20,36 (1964)
Synthesis: Buchi et ai., f. Arner. Chern. Soc., 88,3099 (1966)
Pharmacology: Raymond-Hamet, Rothlin., C.R. Soc. Bioi., 127,592 (1938)
Raymond-Hamet, Rothlin., Arch. inst. Pharrnacodyn., 63, 27 (1939)
Raymond-Hamet., Cornpt. rend., 201,285 (1940)
Raymond-Hamet., C.R. Soc. Bioi., 135, 176 (1941)
Raymond-Hamet, Perrot., Bull. Acad. Med., 24,423 (1941)
Vincent, Sero., C.R. Soc. Bioi., 136,612 (1942)