Indole Alkaloids

Other Names Indolalkaloide, indolamine alkaloids, indole, indoles Indole alkaloids are derived from the indole ring system and appear almost exclusively in the families Apocynaceae501 (Alchornea spp., Alstonia scholaris, Aspidosperma quebracho-blanco, Catharanthus roseus, Rauvolfia spp., Tabernaemontana spp., Tabernanthe iboga, Vinca spp., Voacanga spp.), Loganiaceae (Gelsemium sempervirens, Strychnos nux-vomica, Strychnos spp.), and Rubiaceae (Corynanthe spp., Mitragyna speciosa, Pausinystalia yohimba). Indole alkaloids also occur in certain ascomycetes (Balansia cyperii, Claviceps paspali, Claviceps purpurea, Claviceps spp.), other fungi (Tyler 1961), and several climbing vines (Ipomoea violacea, Turbina corymbosa) (Hofmann 1966; cf. ergot alkaloids). Included among the large group of indole alkaloids (Trojanek and Blaha 1966) are the ~-carbolines with harmaline and harmine; the tryptamine derivates bufotenine, N,N-DMT, 5-MeO-DMT, psilocybin, and psilocin; the ergot alkaloids; and the alkaloids of the ibogane type (ibogaine, voacangine), yohimbane type (yohimbine), and strychnane type (strychnine). Indoles are also found in the genus Uncaria, several species of which are used as ayahuasca additives (Phillipson and Hemingway 1973). Many indole alkaloids are psychoactive or occur in plants that are utilized for traditional psychoactive purposes (Lindgren 1995; Rivier and Pilet 1971; Schultes 1976).

Literature See also the entries for ~-carbolines, ergot alkaloids, and yohimbine. Gershon, S., and W. J. Lang. 1962. A psychopharmacological study of some indole alkaloids. Archives Internationales de Pharmacodynamie et de Therapie 135 (1-2): 31-56. Hesse, M. 1968. Indolalkaloide in Tabellen. Berlin: Springer. Hofmann, Albert. 1966. AlcaloYdes indoliques isoles de plantes hallucinogenes et narcotiques du Mexique. In Colloques internationaux du Centre National de la Recherche Scientifique: Phytochimie et plantes medicinales des terres du Pacifique, Nomea (Nouvelle Caledonie) 28.4-5.5.1964, 223-41. Paris: Centre National de la Recherche Scientifique. Lindgren, Jan-Erik. 1995. Amazonian psychoactive indols: A review. In Ethnobothany: Evolution ofa discipline, ed. Richard Evans Schultes and Siri von Reis, 343-48. Portland, Ore.: Dioscorides Press. Phillipson, John David, and Sarah Rose Hemingway. 1973. Indole and oxindol alkaloids from Uncaria bernaysia. Phytochemistry 12:1481-87. Rivier, Laurent, and Paul-Emile Pilet. 1971. Composes hallucinogenes indoliques naturels. Annee BioI. 3:129-49. Schultes, Richard Evans. 1976. Indole alkaloids in plant hallucinogens. Journal ofPsychedelic Drugs 80 (1): 7-25. Trojanek, J., and K. Blaha. 1966. A proposal for the nomenclature of indole alkaloids. Lloydia 29 (3): 149-55. Tyler, Varro E. 1961. Indole derivatives in certain North American mushrooms. Lloydia 24:71-74.