B-Carbolines

Other Names Beta-carbolines, l3-carbolines, I3Cs l3-carbolines are derived from the actuall3-carboline (norharmane). They belong to the group of indole alkaloids and are closely related to tryptamines. They consist of an indole skeleton and various side chains. The psychoactive effects of l3-carbolines are due primarily to the harmala alkaloids harmaline, harmine, harmalol, harmane (I-methyl-l3-carboline), and norharmane (l3-carboline) (Naranjo 1967). The simpler (l3-carboline) alkaloids occur in numerous plants (Allen and Holmstedt 1980). Many plants that produce psychoactive effects or are utilized for psychoactive purposes contain l3-carbolines (including Acacia spp., Arundo donax, Banisteriopsis caapi, Banisteriopsis spp., Mucuna pruriens, Papaver spp., Passiflora spp., Peganum harmala, Phalaris arundinacea, Phalaris spp., Psychotria spp., Strychnos spp., Virola spp., Tribulus terrestris, and Amanita muscaria). These compounds are also present in tobacco smoke (cf. Nicotiana tabacum) and in many plants that are used traditionally to make ayahuasca or are now used as ayahuasca analogs (Schultes 1982). Many l3-carbolines occur as endogenous substances in animals and in humans, where they serve important functions in the nervous system (Bringmann et al. 1991). They appear to influence both moods and dreaming. It is likely that norharmane (l3-carboline) occupies a specific 13carboline receptor. Harmane is the endogenous MAO (monoamine oxidase) inhibitor, suppressing MAO-A (Rommelspacher et al. 1991). This allows the endogenous N,N-DMT to persist for a longer duration and trigger visionary perceptions that manifest either as spontaneous visions during the waking state or as dreams while sleeping (Callaway et al. 1995). The harmala alkaloids harmaline, harmine, harmane, and tetrahydroharmane are all MAO inhibitors that inhibit primarilyMAO-A (Buckholtz and Bogan 1977; McIsaac and Estevez 1966). In the presence of certain foods, MAO inhibitors are considered to be dangerous or even very dangerous. Tyramine, which is found in such foods as aged cheese, is especially hazardous. If it is not broken down by MAO, it can cause severe toxic effects to an organism. More-recent studies, however, have shown that the dangers have been greatly exaggerated in both the literature and «on the street:' Moreover, the amount of tyramine contained in most "dangerous" foods tends to be rather low (Berlin and Lecrubier 1996).

Literature Allen, J. R. F., and Bo Holmstedt. 1980. The simple l3-carboline alkaloids. Phytochemistry 19:1573-82. Berlin, Ivan, and Yves Lecrubier. 1996. Food and drug interactions with monoamine oxidase inhibitors: How safe are the newer agents? eNS Drugs 5 (6): 403-13. Bringmann, Gerhard, Doris Feineis, Heike Friedrich, and Anette Hille. 1991. Endogenous alkaloids in man-synthesis, analytics, in vivo identification, and medicinal importance. Planta Medica 57 supp!. (1): 73-84. Buckholtz, N. S., and W. O. Bogan. 1977. Monoaminooxydase inhibition in brain and liver produced by l3-carbolines: Structure-activity relationships and substrate specificity. Biochemical Pharmacology 26: 1991-96. Callaway, James C., M. M. Airaksinen, and J. Gynther. 1995. Endogenous l3-carbolines and other indole alkaloids in mammals. Integration 5:19-33. (Includes a very comprehensive bibliography.) McIsaac, W. M., and V. Estevez. 1966. Structureactivity relationship of l3-carbolines monoamine oxidase inhibitors. Biochemical Pharmacology 15:1625-27. Naranjo, Claudio. 1967. Psychotropic properties of the harmala alkaloids. In Ethnopharmacologic search for psychoactive drugs, ed. D. H. Efron, 385-91. Washington, D.C.: U.S. Department of Health, Education, and Welfare. Rommelspacher, Hans, Torsten May, and Rudi Susilo. 1991.I3-carbolines and tetrahydroisoquinolines: Detection and function in mammals. Planta Medica 57 stipp!. (1): 93 ff. Schultes, Richard Evans. 1982. The beta-carboline hallucinogens of South America. Journal of Psychoactive Drugs 14 (3): 205-20. Stohler, R., H. Rommelspacher, D. Ladewig, and G. Dammann. 1993. Beta-carboline (Harman/Norharman) sind bei Heroinabhangigen erhoht. Therapeutische Umschau 50:178-81.