Bufotenine

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Other Names Bufotenin, 5-hydroxy-N,N-dimethyltryptamine, 5-0H-DMT, mappin, N,N-dimethylserotonin, 3[ 2-(dimethylamino)ethyl] -IH-indol-5-01 Substance type: tryptamine (indole alkaloid) Bufotenine was first isolated in 1893 from secretions of the common toad (Bufo vulgaris 1.) (Shulgin 1981). In 1954, it was found in Anadenanthera peregrina. Bufotenine also occurs in the false death cap (Amanita citrina [Schaeff.] S.P. Gray) (Keup 1995, 11; Wieland and Motzell953) and in other members of the genus (cf. Amanita pantherina). Indeed, the symbolic relationship between toads and mushrooms is very interesting in this context (see Amanita muscaria). Bufotenine has also been found in Anandenanthera colubrina (Piptadenia spp.), Arundo donax, Banisteriopsis spp., Mucuna pruriens, and Phragmites australis. Bufotenine is a tryptamine derivative and is closely related to N,N-DMT, 5-MeO-DMT, and psilocybin and psilocin. Chemically, it is almost identical to melatonin (for more on melatonin, see Reiter and Robinson 1996). Bufotenine has been detected in human urine on numerous occasions (Raisanen 1985) and thus we know that it is a natural substance that is metabolized in the human body. The molecule is very stable. Approximately 16 mg is considered to be an effective dosage. The pharmacology of the substance has been little studied. The first report of the hallucinogenic effects of bufotenine was published by Fabing and Hawkins (1956), who tested the substance on prison inmates (probably against their will). This was followed by additional research with humans, including some studies in which the substance was tested under highly unethical conditions by being injected into patients in a closed psychiatric institution without their permission, or even against their will. The patients were administered overly high doses and also subjected to electroshocks and other procedures. In this setting, no visions were reported. It was concluded that bufotenine does not produce visions but has only toxic effects (Turner and Merlin 1959). Subsequent studies strengthened the theory that bufotenine should not be classified as a hallucinogen (Mandell and Morgan 1971). A more recent study using only one subject found no hallucinogenic effects, although changes in the emotional domain were observed (McLeod and Sitram 185). Almost all of the reports have noted that the faces of the test subjects turned red or even purple (Fabing and Hawkins 1956). The belief that bufotenine is not a true psychedelic drug has persisted into the present day (e.g., Lyttle et al. 1996; this study, however, is not based on any personal experiments). In its pure form, bufotenine has never acquired any cultural significance as a psychoactive substance. Bufotenine and Bufo marinus Since ancient times, there have been numerous reports of toads being used to prepare love drinks and other witches' brews, and even witches' ointments (Degraaff 1991; Hirschberg 1988). Researchers (prematurely) dismissed such reports as fantasy. In China and Mesoamerica, there is good evidence for the use of toads in magical brews. Chinese toad secretions (ch'an su) contain large amounts of bufotenine (Chen and Jensen 1929). In China and Japan, preparations containing bufotenine are sold as aphrodisiacs (Lewis 1989, 70).491 In Mesoamerica, the toad was regarded as a manifestation of the Earth Mother, for example, in the form of the Aztec earth goddess Tlatecuhtli (Furst 1972; 1974, 88*). In the region, toads (and frogs) are associated with the rain gods (chac) and rainmaking. The Tarahumara refer to toads as "powerful rainmakers." The Olmecs-whose culture is thought to have been the first Mesoamerican civilization-depicted toads in their sacred art and probably used them as hallucinogens. An Olmec object made of green jade and shaped like a toad has been interpreted as a tray for snuff powder (Peterson 1990,46*). In general, the toad was probably the most important Olmec deity (Furst 1981; Furst 1996*; Kennedy 1982; Taylor n.d.). A cylindrical ceramic container (late Classic period) containing a Bufo marinus (cane toad) skeleton was found in Seibal, a Mayan ceremonial center. It may have been used as a vessel for drinking balche'. Hundreds of ritually interred cane toad skeletons were discovered in postClassic Mayan ritual depots on the Caribbean island of Cozumel (Hamblin 1981; 1984,53 ff.). A report from the colonial period indicates that toads were an ingredient in balche' or chicha. Bufo marinus is also an ingredient in zombie poison. In Mesoamerica, Bufo marinus is known variously as henhen (Tzeltal; cf. Hunn 1977, 247), bab (Mayan), ah bab (Lacandon), and tamazolin (Aztec). Numerous stone sculptures of toads as well as some toad bones were discovered in the main temple (Templo Mayor) of the Aztecs (Ofrenda 23; Alvarez and Ocana 1991, 117, 128). All of the finds suggest that Bufo marinus was used in rituals or had a cosmological significance. Today, some Mexican Indians still eat skinned toads, while their secretions are sold at Mexican brujeria markets as a love powder. The toad itself is invoked as a love magic in magical prayers (oraci6n del sapo). The toad's mucus is rolled into little balls that are then rubbed behind the ear as an aphrodisiac. Many people in Mexico still wear toad-shaped amulets today; they may, for example, be made from amber or obsidian from Chiapas. In the southern part of Veracruz, curanderos ("healers") or brujos ("sorcerers") still use a preparation of Bufo marinus. To prepare it, they capture and kill ten toads. The glands are removed and crushed to produce a paste, to which lime (probably slaked lime) and ashes from a botanically unidentified plant called tamtwili are added. The combination is then mixed in water and boiled until· there is no more "bad smell" (usually all night long). The solution is then mixed with chicha (maize beer) and filtered. The remaining fluid is kneaded into maize dough, lime brine, and five kernels of sprouted maize, and the mixture is laid out in the sun for a few days so that it can ferment, after which it is dried over a fire. This product (piedrecita, "little rocks") is then stored far away from any human dwellings. In earlier times, special huts were used to store this magical substance. For consumption, a few pieces are cut off, ground, and soaked in water. After the insoluble ingredients have settled, the solution is poured off and boiled for a considerable time until it gives off a certain odor. Today, the drink is no longer ingested collectively but is used by only one person at a time under the supervision of a curandero. The effects begin after approximately thirty minutes and are first manifested as an increase in the pulse rate and a shaking of the muscles and limbs, followed by headaches and delirium. This state lasts three to five hours. In former times, the drinking of this brew was an important part of the initiation of boys into adulthood. Sacred songs were sung to the initiate while he was delirious. The initiate was told to allow the visions he was going to experience to impress themselves well upon him (Knab n.d.). It appears that the hallucinogenic effects of Bufo marinus were also known in Argentina, for it is considered there to be one of the "temptations" of Saint Anthony (see Claviceps purpurea) (Rosemberg 1951). Originally from the Americas, Bufo marinus was .introduced to Australia, where it is now known as the cane toad and its secretions are allegedly used as a psychoactive drug. Under Queensland's Drug Misuse Act, bufotenine is an illegal substance in Australia (Ingram 1988,66). In recent years, the press has been reporting increasing cases of toad lickin' (Lyttle 1993), a practice in which the secretions of Bufo marinus are licked off the toad: When licking the expressed secretions (abusers reported that it is possible to "milk" twice a day), a furry sensation on the lips and tongue quickly becomes manifest. Five to ten (up to 30) minutes later, nausea is common, and only 20 to 30 minutes after ingestion, sometimes earlier, hallucinations of various kinds set in, beginning more rapidly and not lasting as long as with LSD. (Keup 1995, 12) The thickened juice of boiled animals is also ingested in Australia (Keup 1995, 14). A decoction of the dried skin (known as cane skin tea) is also used (DerSpiegel32 [1994]: 92). The secretions from Bufo marinus contain catecholamines (dopamine, N-methyldopamine, adrenaline, noradrenaline) and tryptamines (serotonin, N-methyl-serotonin, bufotenine, bufotenidine, dehydrobufotenine), as well as glycoside-like toad toxins (Deulofeu and Ruveda 1971; Lyttle 1993, 523 f.). The skin has been found to contain morphine. The toad toxins (bufotoxine, bufogenine, and bufadienolides) are cardiotoxic and are similar to digitalis in their effects: nausea, vomiting, increase in blood pressure, confusion, and psychotic states (Keup 1995, 12). Smoking is probably the safest method to ingest Bufo marinus secretions, as the burning process apparently destroys the toxic components while leaving the bufotenine intact (Alexander Shulgin, pers. comm.). The ethnobotanist Brett Blosser smoked dried Bufo marinus secretions (approximately 1 mg every few minutes) and reported experiencing tryptamine-like hallucinations similar to those induced by the secretions of Bufo alvarius (cf. 5-MeO-DMT) (B. Blosser, pers. comm.). The few reports of the effects of smoked toad skin indicate that they are hallucinogenic. One Australian user stated, "I am seeing the world through the consciousness of a toad" (Lewis 1989, 71). The following species of toads contain significant amounts of bufotenine: Bufo alvarius (cf. 5MeO- DMT), B. americanus, B. arenarum, B. bufo bufo, B. calamita, B. chilensis, B. crucifer, B. formosus, B. fowleri, B. paracnemis, B. viridis (Deulofeu and Ruveda 1971, 483).

Commercial Forms and Regulations Bufotenine is marketed as bufotenine hydrogen oxalate. In the United States, bufotenine is classified as a Schedule I drug (Shulgin 1981). In contrast, in Germany it is not considered a narcotic and is not illegal (Korner 1994, 1572*). Literature See also the entries for Anandenanthera colubrina and 5-MeO-DMT. Allen, E. R., and W. T. Neill. 1956. Effects of marine toad toxins on man. Herpetologica 12:150-5l. Alvarez, Ticul, and Aurelio Ocana. 1991. Restos oseos de vertebrados terrestres de las ofrendas del Templo Mayor, ciudad de Mexico. In La fauna en el Templo Mayor, ed. B. Quintanar, 105-46. Mexico City: INAH. Chen, K. K., and H. Jensen. 1929. A pharmacognostic study of ch'an su, the dried venom of the Chinese toad. Journal ofthe American Pharmaceutical Association 23:244-5l. Davis, Wade. 1988. Bufo marinus: New perspectives on an old enigma. Revista de la Academia Columbiana de las Ciencies Exactas, Fisicas y Naturales 14 (63): 151-56. Degraaff, Robert M. 1991. The book ofthe toad. Rochester, Vt.: Park Street Press. Deulofeu, Venancio, and Edmundo A. Ruveda. 1971. The basic constituents of toad venoms. In Venomous animals and their venoms, ed. Wolfgang Bucherl and Eleanor E. Buckley, 475-556. New York and London: Academic Press. Fabing, Howard D., and J. Robert Hawkins. 1956. Intravenous bufotenine injection in the human being. Science 123:886-87. Furst, Peter T. 1972. Symbolism and psychopharmacology: The toad as earth mother in Indian America. In Religion en Mesoamerica, XII Mesa Redondo, 37-46. Mexico City: S.M.A. ---. 1981. Jaguar baby or toad mother: A new look at an old problem in Olmec iconography. In The Olmec and their neighbors, ed. E. Benson, 149-62. Washington, D.C.: Dumbarton Oaks. Hamblin, Nancy 1. 1981. The magic toads of Cozumel. Mexicon 3 (I): 10-13. ---. 1984. Animal use by the Cozumel Maya. Tucson: The University of Arizona Press. Hirschberg, Walter. 1988. Frosch und KrOte in Mythos und Brauch. Vienna: Bohlau. Hunn, Eugene S. 1977. Tzeltal folk zoology. New York: Academic Press. Ingram, Glen. 1988. The Australian cane toad. In Venoms and victims, ed. John Pearn and Jeanette Covacevich, 59-66. Brisbane: The Queensland Museum and Amphion Press. Kennedy, Alison B. 1982. Ecce Bufo: The toad in nature and Olmec iconography. Current Anthropology 23 (2): 273-90. Keup, Wolfram 1995. Die Aga-Krote und ihr Sekret: Inhaltsstoffe und MiBbrauch. Pharmazeutische Zeitung 140 (42): 9-14. Knab, Tim. n.d. Narcotic use of toad toxins in southern Veracruz. Unpublished manuscript. (Ten typewritten pages.) Lewis, Stephanie. 1989. Cane toads: An unnatural history. New York: Dolphin/Doubleday. Lyttle, Thomas. 1993. Misuse and legend in the "toad licking" phenomenon. The International Journal ofthe Addictions 28 (6): 521-38. Lyttle, Thomas, David Goldstein, and Jochen Gartz. 1996. Bufo toads and bufotenine: Fact and fiction surrounding an alleged psychedelic. Journal of Psychoactive Drugs 28 (3): 267-90. (Contains an excellent bibliography.) Mandell, A. J., and M. Morgan. 1971. Indole(ethyl)amine N-methyltransferase in human brain. Nature 230:85-87. McLeod, W. R, and B. R Sitram. 1985. Bufotenine reconsidered. Psychiatria Scandinavia 72:447-50. Raisanen, Martti. 1985. Studies on the synthesis and excretion of bufotenine and N,Ndimethyltryptamine in man. Academic dissertation, Helsinki, University of Helsinki. Reiter, Russel J., and Jo Robinson. 1996. Melatonin. Munich: Droemer Knaur. Rosenberg, Tobias. 1951. El sapo en el folklore y en la medicina. Buenos Aires: Editorial Periplo. Shulgin, Alexander T. 1981. Bufotenine. Journal of Psychoactive Drugs 13 (4): 389. Taylor, Michael. 1993. The use of the Bufo marinus toad in ancient Mesoamerica. Crash Collusion 4: 53-55. Turner, W. J., and S. Merlis. 1959. Effects of some indolalkylamines on man. Archives ofNeurology and Psychiatry 81:121-29. Verpoorte, R., Phan-Quoc-Kinh, and A. Baerheim Svendsen. 1979. Chemical constituents of Vietnamese toad venom collected from Bufo melanostictus Schneider. Journal of Ethnopharmacology 1:197-202. Wieland, Theodor, and Werner Motzel. 1953. Dber das Vorkommen von Bufotenin im gelben Knollenblatterpilz. Justus Liebigs Annalen der Chemie 581:10-16.