Bufotenine Abstracts

BOSFELD, JANE
Toad Tripping
OMNI; Dec 1989
It's not exactly a craze, but licking toads is the latest - and certainly the wierdest - way to get high. ''It is not a big problem, but when people hear about it they try it,'' explains Robert Sager, chief of the US Drug Enforcement Administrations's Western Regional Laboratory in San Francisco. The toad of choice is the Cane Toad, a tropical green and red toad that's a favorite among aquarium habitues. It secretes a toxin, called bufotenine to ward off predators. Ingesting bufotenine - by licking the toad, or killing it and boiling it's skin for a foul-tasting tea - will give you a high similar to that of psilocybin (a hallucinogen found in certain mushrooms). But, Sager warns, bufotenine will ''make you ill, and it is not terribly hallucinogenic. It's just not that great a high.'' Of course for those who don't mind licking a tailless amphibian, it might be possible to buy several and keep them on hand: Once a toad has been licked it secretes more bufotenine, so replenishing the supply would not be a problem. Although four Australians croaked last summer after drinking an especially strong batch of Cane-skin tea, no fatalities have been reported in this country. But, says Sager, a number of people have been hospitalized. Nevertheless, possessing a Cane Toad is not illegal if you do it for reasons other than getting high.

CARPENTER, WILLIAM T; FINK, EDWARD B; NARASIMHACHARI, NEDATHUR; HIMWICH, HAROLD
A test of the transmethylation hypothesis in acute schizophrenic patients.
American Journal of Psychiatry; 1975 Oct Vol 132(10) 1067-1071
An investigation of 3 aspects of the transmethylation hypothesis found that 26 acutely schizophrenic patients were no more likely to have bufotenine or N,N-dimethyltryptamine present in urine or elevated serum indolethylamine N-methyltransferase activity than 10 normal controls. It is concluded that these are naturally occurring substances.

CERLETTI A
Teonanacatl und Psilocybin (Teonanacatl and Psilocybin)
Deutsche med.Wchnschr. 84:2317 (1959)
The introductory part of this study reviews the history of the Mexican hallucinogenic fungi from the first description of Psilocybe mexicana by an European (Bernardine de Shagin) in the 16th century to the most recent research of the Americans V.P. and R2EG. Wasson and the French mycologis, Heim. The next part deals with the chemistry of the substances contained in Psilocybe mexicana. These were isolated and their structure elucidated in our laboratories. The relation of Psilocybin and Psilocin to other 'psychopharmaca' with an indole structure (LSD, serotonin, bufotenin) is shown by means of formulae. In the third part of the study, the pharmacology of Psilocybin is discussed. In the last part, the effect on human beings is described. At the end of this part, therapeutic use of LSD is also mentioned and similarities and differences between Psilocybin and LSD are sketched.

CHILTON; BIGWOOD; JENSEN
Psilocin, bufotenine & serotonin
Journal of Psychedelic Drugs; Vol. 11(1-2) Jan-Jun 1979
[Excerpt] We have investigated the biosynthesis of psilocin in a strain of Psilocybe cubensis from the Amazon valley, employing the non-radioactive deuterium label. Experiments were carried out to find the smallest size culture which would reliably produce mushrooms in order to maintain a high concentration of deuterated compounds without having to use a large amount of labeled compounds. Although mushrooms were obtained on a litle as 17 grains of rye, a more reliable fruiting mass was obtained on minicultures of 10 g rye grain in 15 g water. Two weeks after inoculation the minicultures were cased with vermiculite, peat moss, sand and crushed oyster shell. Fruiting occurred five to six weeks after inoculation. The yield of mushrooms appeared relatively unaffected by addition of up to 100 mg of tryptamine to 10 g of rye grain. Minicultures continued to produce mushrooms for up to 20 weeks, and average minicultures produced a total of 2.7 g dry weight of mushrooms. Minicultures actually produced a higher yield of mushrooms per g of rye grain than did larger scale cultures.

CORBETT, L; ET AL
Hallucinogenic N-methylated indolealkylamines in the cerebrospinal fluid of psychiatric and control populations.
British Journal of Psychiatry; 1978 Feb Vol 132 139-144
Studied the incidence and quantities of dimethyltryptamine and O-methyl-bufotenine in the cerebrospinal fluid of 50 patients with acute schizophrenic illnesses and in 34 surgical and 16 neurological controls. Results show that some schizophrenics had higher levels of both amines than did controls, although the differences in distribution did not reach statistical significance.

FAURBYE, ARILD; PIND, K
The presence of N-methylated and N-acetylated indole amines in the urine of schizophrenics and controls.
Foreign Psychiatry; 1973 Sum Vol. 2(2) 3-10
Used gas and thin-layer chromatography to test for the presence of 3 toxic amines in the urine of 4 female schizophrenics and 3 female nurses. The amines found in the urine of both groups were dimethyltryptamine, (DMT), bufotenine, and 5-methoxy-N,N-dimethyltryptamine (5-MODMT). These amines may, therefore, be regarded as normal metabolic products. It is noted that DMT can produce schizophreniform symptoms in humans. Data is presented suggesting that the effects of 5-MODMT are similar to those of DMT and that 5-MODMT may be a more potent drug. Difficulties in determining the specific amine content in urine are noted.

FISH; JOHNSON; HORNING
Piptadenia Alkaloids. Indole Bases of P2Eperegrina and Related Species.
American Journal of Chemistry; Vol.77 pp 5982-5895 (November 1955)
Four indole bases have been found to occur in the seeds and pods of P. peregrina (L.) Benth. and P.macrocarpa Benth. The pods contain N,N-dimethyltryptamine, and the seeds contain bufotenine, bufotenine oxide and N,N-dimethyltryptamine oxide. In addition, a 5-hydroxyindole base of unknown structure was found in P. macrocarpa seeds 2E EXPERIMENTAL: Examination of Snuff: Several samples of laboratory snuff were prepared from P. peregrina seeds of Puerto Rican origin using the descriptions of Humboldt and Spruce as a guide[2]. They were (1) a coarsely ground sample of seeds was roasted at 175F8 for 40 minutes, followed by mortar grinding (2) preparation of (1) was repeated with the addition of calcium carbonate before heating, and (3) a fermented sample of seeds was dried and ground. A few milligrams of each snuff sample was taken for comparison with the same amount of authentic snuff obtained from a snuff box now in the Smithsonian Institution. The solids were ground thoroughly with about 02E5 ml. of ethanol; the solutions were placed on S.&S.589R paper and developed in a propanol-ammonia system. Relatively good resolution was obtained. One area of major intensity corresponding to bufotenine was present for all samples. Two additional areas were common to the laboratory and authentic snuff chromatograms. Two faint areas present for the authentic snuff were not present for the laboratory samples. The colors of the common areas were identical. Ehrlich's reagent was used as a spray.

GEYER, MARK A; ET AL
Opposite effects of intraventricular serotonin and bufotenin on rat startle responses.
Pharmacology, Biochemistry and Behavior; 1975 Jul-Aug Vol 3(4) 687-691
In 2 experiments the startle responses of a total of 34 male Sprague-Dawley rats to air puffs were monitored in a stabilimeter during the iv infusion of various doses of 5-hydroxytryptamine (5-HT) or the putative hallucinogenic congener of 5-HT, 5-hydroxy-N,N-dimethyltryptamine (5-HDMT) or saline. Qualitatively opposite effects were observed, with 5-HT producing a dose-dependent decrease in responsivity and 5-HDMT increasing the magnitude of startle responses. No specific effects of either compound could be demonstrated on the presumably separable processes of sensitization and habituation. Results are discussed in the context of a central serotenergic system which facilitates behavioral inhibition and which is antagonized by indoleamine hallucinogens.

MCCLUE, STEVEN J; bRAZELL, CELIA; STAHL, STEPHEN M
Hallucinogenic drugs are partial agonists of the human platelet shape change response: A physiological model of the 5-HT2 receptor.
Biological Psychiatry; 1989 Jul Vol 26(3) 297-302
Assayed several phenylalkylamine and indolealkylamine hallucinogens, as well as structurally similar nonhallucinogens, for their effect on human platelet shape change, a physiological model for the central serotonergic 5-hydroxytryptamine (5-HT)2 receptor. The hallucinogenic drugs lysergic acid diethylamide (LSD-25), N,N -dimethyltryptamine, 5-methoxy- N,N -dimethyltryptamine 4-iodo-2,5-dimethoxyphenylisopropylamine, bufotenine, and mescaline all showed a characteristic 5-HT2 partial agonist effect on platelet shape change. Data suggest that some of the behavioral effects of LSD-type hallucinogens in humans are due to their actions at 5-HT2 receptors and that these hallucinogens are partial 5-HT2 agonists.

MELTZER, HERBERT Y; FESSLER, RICHARD G; SIMONOVIC, MILJANA; FANG, VICTOR S
Stimulation of rat prolactin secretion by indolealkylamine hallucinogens.
Psychopharmacology; 1978 Vol 56(3) 255-259
The hallucinogenic indoleamine drugs N,N-dimethyltryptamine (DMT), psilocybin, bufotenin, 5-methoxy-N,N-dimethyltryptamine, and N-methyltryptamine increased plasma prolactin (PRL) levels in male Sprague-Dawley rats. The increase in plasma PRL produced by DMT, psilocybin, and bufotenin was inhibited by methysergide, a serotonin receptor blocker. Parachlorophenylalanine (PCPA), an inhibitor of serotonin synthesis, significantly potentiated the increase in PRL produced by DMT andpsilocybin. Parachloroamphetamine, a relatively selective toxin for serotonin neurons, also stimulated the increase in PRL produced by DMT. These results suggest that the indole hallucinogens stimulate PRL secretion by a serotonergic agonist mechanism. Bufotenin has been reported to pass the blood/brain barrier poorly, but of the indoles studied it had the most potent effect on PRL secretion. This raises the possibility that the serotonin receptors that promote PRL secretion may be outside the blood/brain barrier or that the central 5-hydroxytryptamine receptors that mediate PRL secretion may be especially responsive to bufotenin.

MORGAN, ADRIAN
Who put the toad in toadstool?
New Scientist, 25-Dec-1986/1-JAN-1987 Vol 112 pg 44
Discusses the historical and legendary links between toads and toadstools, and their use in witches brews, the pharmacology and effects of toad venoms and the use of these in ethnomedical practices in many cultures on several continents. The history and mythography of hallucinogenic mushrooms, and the use of bufotenine from toads as an intoxicant are recounted.

NICHOLS, DAVID E; GLENNON, RICHARD A
Medicinal Chemistry and Structure Activity Relationships of Hallucinogens
Hallucinogens: Neurochemical, Behavioural, and clinical Perspecives, edited by B. L. Jacobs. Raven Press, New York 1984 p. 123-124
The 5-hydroxy derrivative of DMT, bufotenine, or N,N-dimethyl-serotonin, is another naturally occuring tryptamine found to occur in South American Snuffs (also Bufo). Intravenours administration of of bufotenine was reported by Fabing and co-workers (59,60) to be hallucinogenic in man. THis finding is in conflict with a later report by Turner and Merlis (253). Apparantly, due to its low lipid solubility (65), bufotenine does not readily cross the blood-brain barrier (64,183). The initial observations made by Fabing et.al. (59,60) may be the result of peripheral toxic manifestations.

Bufotenine has been found to be behviourally inactive, or only weakly active in most animals studies...

PIGGOTT, L R
Overview of selected basic research in autism.
Journal of Autism and Developmental Disorders; 1979 Jun Vol 9(2) 199-218
A review shows that there is mounting indication, but inconclusive evidence, of unique physiologic disturbances etiologically related to autism. Additionally, there is indication that some of the physiologic disturbances found in autistic children are also present in children with other developmental disorders. Children called autistic probably represent a complex of clinically similar manifestations in a variety of subgroups of children, each subgroup representing a basically different physiologic disturbance. However, the possibility remains that there is only one basic disturbance that in varying degrees affects many body systems and manifests in a variety of overlapping syndromes. Objective markers are needed to allow the demarcation of subgroups of autistic children for further study. Possible markers may be decreased duration of postrotatory nystagmus, auditory evoked response deviations, lymphocytic hyporesponsivity, increased blood platelet serotonin efflux, and/or the presence of urinary N-N dimethyltryptamine or bufotenin.

ROSENGARTEN, HELEN; FRIEDHOFF, ARNOLD J
A review of recent studies of the biosynthesis and excretion of hallucinogens formed by methylation of neurotransmitters or related substances.
Schizophrenia Bulletin; 1976 Vol 2(1) 90-105
Reviews recent evidence on the transmethylation hypothesis of schizophrenia: that a metabolic aberration in a methylating system could lead to the formation of hallucinogenic substances resembling mescaline in structure or that hallucinogens might also be formed from serotonin or tryptamine, compounds that could be transformed to bufotenine or dimethyltryptamine (DMT), which are present in some psychotomimetic agents. Five specific conclusions about enzymes involved in the biosynthesis of hallucinogenic substances are presented. It is noted that the main problem in current research on the transmethylation hypothesis is adequate compound identification. The need for both definitive assessments of the relationship of endogenous hallucinogens to the various psychotic states conducted with drug-free Ss and longitudinal studies of symptoms and chemical parameters is stressed.

SCHULTES; HOFMANN
The Chemistry of Yopo
Plants of the Gods; pg 118
THE CHEMISTRY OF YOPO: The active principals of Anadenanthera belong to both open-chained and ring tryptamine derivatives and, therefore, to the important class of indole alkaloids. Tryptamine is also the basic compound of the amino acid tryptophane, widely distributed in the Animal Kingdom. Dimethyltryptamine (DMT) and 5-hydroxydimethyltryptamine (bufotenine) are representatives of the open-chained Anadenanthera tryptamines. Bufotenine has also been found in the skin secretion of a toad (Bufo sp.) - hence its name. Ringed tryptamine derivatives found in Anadenanthera are 2-methyl- and 1,2-dimethyl-6-methoxytetrahydro-beta-carboline.

SHULGIN A T
Hallucinogens
Burger's Medicinal Chemistry; Fourth Edition, Volume III. pg. 1123-1124
Substitution of the indolic 5 position leads to compounds that are structurally similar to the neurotransmitter serotonin. The simplest structure is 5-hydroxy-N,N-dimethyltryptamine (bufotenine) which has already been discussed as as cardiovascular stimulant that has bveen misassigned as a hallucinogen. Methylation of the 5-hydroxy group leads to the formation of the parenterally active hallucinogenic 5-MeO-DMT effective in the 5-10 mg. range. It has been reported as a natural component of several snuff mixtures used by the Indians in the New World. It is of exceptionally short duration of action, the initial intoxication occurring within seconds of administration, and the entire recovery completed usually within 15 minutes.

SHULGIN AT
Profiles of psychedelic drugs. 11. Bufotenine.
J. Psychoactive Drugs 13: 389. (1981) [#124]
[No Abstract]

SPOERKE DG; HALL AH
Plants and mushrooms of abuse.
Emerg Med Clin North Am. 1990 Aug; 8(3): 579-93
The plants described earlier are only a few of those that can be misused. Most have effects similar to those of more popular synthetic drugs but can cause unpleasant side effects and unpredictable results. Identification of the offending botanic agent can be problematic. These plants are still used because most are legal to possess, and they do produce desired hallucinogenic and stimulant effects. Because the active ingredients are similar pharmacologically to agents such as LSD and amphetamine, required treatment is often similar. The challenge for the Emergency Department physician is to recognize the potential for abuse of these botanic agents, their probable side effects, and the need for appropriate, usually supportive, treatment. There are many more plants with abuse potential than can be discussed in detail in an article of this size. Table 1 lists a number of other agents that might be misused. Phenylamine hallucinogens occur in several species and include N,N-dimethyltryptamine (DMT), N-monomethyltryptamine (MMT), 5-methoxy-N-N-dimethyltryptamine (5-MeO-DMT), 5-methoxy-N-monomethyltryptamine (5-MeO-DMT), 5-methoxy-N-monomethyltryptamine (5-MeO-MMT), 5-hydroxy-N-N-dimethyltryptamine (bufotenine or 5-H-DMT), and N,N-dimethyltryptamine-N-oxide (DMT-N-oxide).

STROMBERG VL
Isolation of Bufotenine from Piptadenia peregrina.
Journal American Chemical Society Vol.26 (March 1954)
The inhalation of narcotic snuff by the natives of Haiti was a common practice at the time of the discovery of the West Indies. This snuff, called cohoba, was used by the necromancers or priests in their ceremonies and was supposed to enable them to communicate with unseen powers. ... Piptadenia peregrina seeds, 891 grams, secured from Las Mesas, Puerto Rico... Through the Agricultural Research Service, Plant Exporation and Introduction, United States Department of Agriculture.

STROMBERG, VERNER L
The Isolation of Bufotenine from Pipatdenia peregrina.
Journal of the American Chemical Society; Vol 76 pg 1707 (20-Mar-1954)
EXPERIMENTAL: Isolation of Bufotenine. - Piptadenia peregrina seeds, 891 grams, secured from Las Mesas, Puerto Rico, were ground in a Waring blendor and extracted twice with 4 litres of 1% ethanolic tartaric acid solution for 2 hours at 55F8. The resulting 8 litre of solution was filtered, concentrated to a volume of 1 liter and diluted with 2.5 liters of water. It was acidified with 200 ml of 2N hydrochloric acid. The solution was filtered and extracted six times with 200 ml portions of chloroform. The chloroform solution was discarded. The acid solution was neutralized with solid sodium carbonate. This was divided into two parts and each part was extracted seven times with 200 ml portions of chloroform. The combined chloroform solutions were extracted with 2N hydrochloric acid. This acid solution was made basic with solid sodium carbonate and the base was re-extracted with chloroform. After drying, the solvent was removed to provide 20.95 grams (2.45%) of mixed organic bases. A crude alkaloid fraction, 10.11 grams, was subjected to chromatographic separation on alumina (Merck Reagent). An ethyl acetate fraction contained 0.12 gram of a brown oil. The bufotenine fraction was eluted with 3:1 ethyl acetate-ethanol to give 7.66 grams of material. Several recrystallizations from ethyl acetate gave 4.09 grams (40% of the alkaloid fraction), melting point 146F8-147F8. Bufotenine represents 0.94% of the Piptadenia seed. The material remaining on the column was eluted with ethanol to give 2.31 grams of residue.

STROMBERG, VERNER L
The Isolation of Bufotenine from Pipatdenia peregrina.
Journal of the American Chemical Society; Vol 76 pg 1707 (20-Mar-1954)
The inhalation of a narcotic snuff by the natives of Haiti was a common practice at the time of the discovery of the West Indies. This snuff, called cohoba, was used by the necromancers or priests in their ceremonies and was supposed to enable them to communicate with unseen powers. The ceremonial use of cohoba was described as early as 1496 by Ramon Pane who was with Columbus on his second voyage, but in later years cohoba was confused with tobacco. The chemistry of this snuff has never been studied although the leguminous shrub Piptadenia peregrina is now known to be its source. [1] In the present work there was isolated from the seeds of this plant a crystalline organic base, m.p. 146-147F8, with empirical formula C12H16N2O in 0.94% yield. The ultraviolet absorption spectrum in 02E1 N hydrochloric acid showed a maximum at 295 mE6, a shoulder with a se cond maximum at 247 mE6. In 0.1 N sodium hydroxide the absorption spectrum shows a shift of the second maximum to 322 mE6. This shift is similar to that observed for the vasoconstrictor 5-hydroxytryptamine (serotonin). [2] A methiodide, picrate, oxalate and m-nitrobenzoate were prepared. The melting points were in good agreement with the literature values for bufotenine2E ... The infrared absorption spectrum of the picrate was identical to that of a picrate of a synthetic sample kindly supplied by Dr. M. E. Speeter of the Upjohn Company. The seeds of Piptadenia peregrina evidently comstitute an excellent source of bufotenine. The leaves and branches do not give an alkaloid test with Meyer's or silicotungstic acid reagents. The seed pods give only a slight positive test.

SZARA S
Psychotomimetic Drugs
Psychotomimetic Drugs; Ed.:Efron2E Raven Press (1970) pg 286 RM315.P77
The isolation of bufotenine and dimethyltryptamine by Fish, Johnson, Horning & Stromberg from the seeds of Piptadenia peregrina was made, I think, 15 years ago. They had a sample of seeds grown in Puerto Rico, and it so happens that the amounts of these well known tryptamines vary with location, soil, and season. This sample, which is still available (I have analysed it myself since), happened to contain bufotenine and dimethyltryptamine, whereas other samples of Piptadenia that I have analysed so far contain as the main component 5-methoxy-N,N-dimethyltryptamine, and small amounts of dimethyltryptamine.