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.
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)
