Bufotenin
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Contents
- 1 Brief overview - What is Bufotenine?
- 2 Chemical and physical properties
- 3 Effects
- 4 Pharmacology, toxicity and general safety
- 5 Life forms containing bufotenine
- 6 Extraction teks
- 7 Dosages and consumption methods
- 8 History of usage
- 9 Analysis of bufotenine
- 10 Scientific publications
- 11 Other links of interest
Brief overview - What is Bufotenine?
Bufotenine (5-HO-DMT) is a psychoactive alkaloid found in several plants and animals, also in humans. It is known specially for it's presence in the skin and venom of some toads (Bufo species, hence the name BUFOtenine)
Chemical and physical properties
For solubility, melting point, etc, check the Bufotenine Chemical and Physical Properties WIKI
Bufotenine can be oxidized (naturally or with the use of hydrogen peroxide), and becomes Bufotenine N-Oxide
Effects
Pharmacology, toxicity and general safety
Jonathan Ott - Pharmañopo (bufotenine activity article)
Life forms containing bufotenine
Amanita spp.
(Generally low concentration. Ref Trout's Notes)
- Wieland & Motzel 1953 (European specimens) 0.045% bufotenine (Stijve 1979 noted their inefficient procedure may have only recovered 10% of what was there.)
- Bufotenine presence. Catafolmo & Tyler 1961 (North American specimens)
- Bufotenine presence. Tyler 1961 (North American specimens)
- Bufotenine presence.Tyler & Groger 1964 (Gennan specimens) Identified chromatographically. (Mycelium shown to contain 0.03%)
- Stijve 1979 (German, Dutch & Swiss specimens). Bufotenine was the major alk. Bufotenine concentrations were estimated from 0.70- 1.5% using GLC and from 0.4-1.3% using tlc. Isolation: 0.8% in cap. 1.5% iu stalk & 0.065% in bulb. Wurst et al. 1992 (0.0 - 1.899%)
- Bufotenine presence. Wieland & Motzel 1953 (observed)
- Catalfomo & Tyler 1961 could not verify
- Stijve 1979 could not detect it
- Wieland & Motzel 1953 (Bufotenine observed)
- Brady & Tyler 1959 could not detect.
- Stijve 1979 could not detect it
- Bufotenine presence. Catafolmo & Tyler 1961 (North American specimens)
- Bufotenine presence. Tyler 1961 (observed)
- Bufotenine presence. Tyler & Groger 1964 (German specimens) Identified chromatographically.
- Bufotenine presence. (0.374 & 0.617%) Wurst et al. 1992
- Bufotenine presence(0.018-0.020%). Wurst et al. 1992
- Stijve 1979 could not detect it
- Tyler 1961 (Bufotenine presence observed)
- Overview & summary: see Catalfomo & Eugster 1970
Anadenanthera spp.
Anadenanthera spp.
- Analyzing seeds, known to be used in preparing parica, collected in Brazil during the first half of the 1800s, DeSmet & Rivier 1987,reported finding only bufotenine. They thought that any other tryptamines may have degraded over time. They noted that Schultes et al. 1977, reported that 2 year old Anadenanthera seeds were observed to go through a similar change in composition while in storage and that Spruce's 1854 collection of A. peregrina seeds also yielded only bufotenine. [Identification of Anadenanthera species cannot reliably be made from seeds alone.] [It should be mentioned that Holmstedt & Lindgren 1967 detected both DMT and bufotenine in seeds that had been collected in 1948 and DMT and 5-MeO-DMT in seeds collected in 1956. Similarly Torres et al. 1991 detected DMT, 5-MeO-DMT and bufotenine in snuff dated to 780 AD]. Ref Trout's Notes
- "epena" Obtained from the Waica by George Seitz. Bufotenine was a minor component, Holmstedt 1965. Because of this, the claimed plant source (Virola) has been questioned. (Seitz claimed to have witnessed the preparation of the material from Virola. In light of the ambiguities uncovered in snuff analysis, we do not think this can automatically be considered to be an Anadenanthera snuff without further study. Our suspicion is that the botanical sources of snuffs remain incompletely characterized.) 5-MeO-DMT was the major alkaloid. (DMT also present as a minor)
- "epena" Snuff prepared, by Ma-hekodo-teri of the Rio Mavaca, from seeds of an Anadenanthera species. Bufotenine [with Bufotenine-N-oxide, DMT and
DMT-N-oxide) Marini-Bettolo et al. 1964 ref Trout's Notes
- "yopo" Snuff prepared, by Pixasi-teri (or Bisashi-teri) of Upper Orinoco, from an Anadenanthera species seeds Bufotenine [5-MeO-DMT also present] (Marini-Bettolo et al. 1964)
- "yopo" Snuff collected in Colombia (collected 1956) Bufotenine (DMT and 5-MeO-DMT also present] Holmstedt & Lindgren 1967 ref Trout's Notes
- "parica" Snuff prepared by Piaroa Indians (collected 1955) Bufotenine [DMT and 5-MeO-DMT also present) Holmstedt & Lindgren 1967 ref Trout's notes
- Snuff: "yopo" Believed to have originated from A . peregrina seeds; showed only bufotenine- 160 mg from 6 gm of snuff. (2.67%). De Budowski et al. 1974 ref Trout's Notes. Another Yopo sample showed only 5-MeO-DMT and was thought to be derived from a Virola species instead.
- Snuff: " epena". Bufotenine present. Yanomamo snuff prepared from Piptadenia peregrina. (Marini-Bettolo et al. 1964)
- 2.1% bufotenine yield from seeds collected in autumn near Rio de Janeiro. Voucher prepared. (Pachter et al. 1959)
- Conflicting reports. Most accounts found only bufotenine in the seeds but several reports exist of the additional presence of DMT and/or 5-MeO-DMT. Torres et al. 1991 reported the detection of all three in snuff powder recovered from archaeological sites in Argentina believed to have been derived from A. colubrina seeds. Both A. colubrina and A. colubrina var. cebil occur in Argentina. While it is not clear which Torres and coworkers referred to, the latter is implied. No analysis of seeds or verifiable plant material were reported in Torres et al 1991
- Modern unpublished analysis of seeds from Argentinean A. colubrina var. cebil found only bufotenine in material that proved active in humans used
as a snuff or when smoked. ref Trout's Notes
- var. cebil (= Piptadenia macrocarpa). Bufotenine Present in seeds. Not detected in pods: Fish et al. 1955. Material from both Florida and Brazil were used. ref Trout's Notes
- var. cebil In seeds and lower in seed pods. Iacobucci & Ruveda 1964. ref Trout's Notes
- var. cebil. Bufotenine 12.4% in seeds from a shaman's garden at Mision Wichi [Highest reported concentration of bufotenine in a
plant] , 4.41 % in a sample of seeds from Salta, 3.51% (seeds) and 0.05% (pods) in a second Salta collection. Only traces were found in bark from Cerro San Bernardo (All in Argentina). Torres & Repke 1996. ref Trout's Notes
Anadenanthera excelsa (as Piptadenia excelsa)
- In seeds. Lower concentration than P. macrocarpa. Iacobucci & Ruveda 1964
Anadenanthera falcata (as Piptadenia falcata)
- Major alkaloid in seeds. Giesbrecht 1960 ref Trout's Notes
- 1.1% bufotenine in seeds. Periera 1957 ref Trout's Notes
- Major alkaloid in seeds. (Haiti) Paris et al. 1967 ref Trout's Notes
- Present in seeds. Not detected in pods Fish et al. 1955. ref Trout's Notes. Material from both Puerto Rico and Brazil were used
- Present in seeds. Alvares Pereira & de Oliveira 1961 ref Trout's Notes
- Present in seeds Stromberg 1954 ref Trout's Notes
- R. Spruce # 119; Rio Negro, Brazil, collected in 1854) ( 1977 analysis). Seeds: 0.6% Bufotenine [614 mg/100 gm dry; Sole alkaloid. Schultes et al. 1977 ref Trout's Notes
- (as Piptadenia peregrina) Seeds collected in Puerto Rico during 1948 Bufotenine (DMT also present] Holmstedt & Lindgren 1967 ref Trout's Notes
- R.E.Scbultes, S.von R.Aitschul & B.Holmstedt, sin. num.; La Carolina, Barrio St. Just, near San Juan, Puerto Rico, December 1974. Same colony as Schultes 26363.]- Bufotenine in Mature seeds collected in March 1975; hill behind El Comandante horse racing track.
1975 analysis (5 months afler collection):No quantification - Bufotenine - 80% of total alkaloid; 1977 analysis of same material: 3.5% Bufotenine [3523 mg / 100 gm dry; Bufotenine was sole alkaloid present. Schultes et al 1977 ref Trout's Notes
- R. E. Schultes 26363: La Carolina, Barrio St. Just, near San Juan, Puerto Rico, Dec. 1972. In mature seeds collected December 1972: 0.01% Bufotenine [6% of 209 mg of total alkaloid/ 100 gram dry]; Seedlings 0.00025% Bufotenine [1 % of 25 mg of total alkaloid/ 100 gm dry]; Pods without seeds 0.00013% Bufoteni ne [1 % of 13 mg of total alkaloid / 100 gram dry]; Twigs 0.0004% Bufotenine 1 % of 38 mg of total alkaloids / 100 gm dry]; Roots [0.69% total alkaloid) 0.007% Bufotenine (1% of 699 mg of total alkaloid / 100 gm dry]. Schultes et al. 1977 ref Trout's notes
- Collected in southern Venezuela. Seeds- 7.5% bufotenine Schultes et al. 1977 cited Chagnon et al. 1970 & 1971 ref Trout's Notes
- [No.24625; Origin: Boa Vista, Brazil] Traces of bufotenine in dry bark. Agurell et al. 1969 ref Trout's notes
Arundo spp.
- Bufotenine In leaf and rhizome. 180 mg from 700 grams of rhizome. Ghosal et al. 1969 ref Trout's Notes
- Bufotenine 128 mg from 200 grams of dry plant. 110 plus 18 mg. Dutta & Ghosal 1967 ref Trout's Notes
- Bufotenine In flowers. Ghosal et at. 1971 ref Trout's Notes
Desmodium spp.
- Bufotenine major alkaloid in stem (0.04% by dry weight; If they used all of their picrate they would have recovered 4.3 gm of bufotenine base from 10.75 kg of stems.) Ueno et al. 1978 ref Trout's Notes
- Bufotenine in Leaf (68 mg. from 2 kg. of dry leaves.) Ghosal et al. 1972a ref Trout's Notes
- Bufotenine in Whole plant (Minor alkaloid) Ghosal & Mukherjee 1964; (Mention) Ghosal & Mukheijee 1965; (Amount not given) Ghosal & Mukherjee 1966 ref Trout's Notes
- Bufotenine in Stem and leaf of young seedling [0.011% by dry weight; 9% of 0.12% Total alkaloid] Ghosal et al. 1972c ref Trout's Notes
Lespedeza spp.
Lespedeza bicolor Turcaninow var japonica Nakai Present in both leaf and root bark. Morimoto & Matsumoto 1966 ref Trout's Notes
Mimosa spp.
- May be in error? Not observed by Gupta and coworkers ref Trout's Notes
Mucuna spp.
Mucuna pruriens In root, stem-leaf and pod. Ghosal (1972a ref Trout's Notes)
Osteophloem spp.
- Schultes & Rodriguez No. 26126; Origin: Manaos, Brazil. - Bufotenine in bark. One of 3 alkaloids in 0.62 mg of total alkaloid from 100 grams of dry bark. This is the only report of this compound being observed in a member of the Myristiacea. Holmstedt et al. 1980 ref Trout's Notes
- Plowman, Schultes & Tovar # 7095; Origin: Pebas. Peru (Alpha-Helix 1977) assayed negative with Dragendorff and Ehrlich reagents. ref Trout's Notes
Piptadenia spp.
- In seeds [with "related substances". Much lower concentrations than peregrina or Cebil. Von Reis Altschul 1964 page 7 cited a letter from M.S. Fish dated 7 January 1958. ref Trout's Notes
- In seeds (with "related substances" . Much lower concentrations than peregrina or Cebil. von Reis Altschul 1964 page 7 cited a letter from M.S. Fish dated 7 January 1958. Also by Yamasato et al. 1972 (TLC). Ref Trout's Notes
- In seeds [with "related substances". Much lower concentrations than peregrina or Cebil. von Reis Altschul 1964 page 7 cited a letter from M.S. Fish dated 7 January 1958. ref Trout's Notes
- In seeds by TLC. Yamasato et al. 1972. Ref Trout's Notes
Phalaris spp.
- Bufotenine present in all fresh samples they examined but not in all dried samples and if so was present in considerably reduced amounts. Culvenor et at. 1964
- Bufotenine traces both in commercial material and in AQ-1 (Italy). HPLC by Fabio Calligris. Festi & Samorini 1994b ref trout's Notes
- Australian commercial - Bufotenine Trace. Baxter & Slaytor 1972b ref Trout's Notes
- (France) Bufotenine traces reported (HPLC) Festi & Samorini 1994b ref Trout's Notes
- (Portugal) Bufotenine Traces reported (HPLC) Festi & Samorini 1994b ref Trout's Notes
- (Portugal) Bufotenine Traces reported (HPLC). Festi & Samorini 1994b ref Trout's Notes
- (Romania) Bufotenine Traces reported (HPLC) Festi & Samorini 1994b ref Trout's Notes
- (France) Bufotenine Traces reported (HPLC) Festi & Samorini 1994b ref Trout's Notes
Phalaris tuberosa ( see P aquatica)
Phragmites spp.
- Bufotenine in Rhizome. Not quantified. Wassel et al. 1985 ref Trout's Notes
Umbellularia spp.
- Bufotenine presence - Shulgin & Shulgin 1997
Urtica spp.
- Bufotenine presence. Shulgin & Shulgin 1997
Virola spp.
- The listing of bufotenine for this species IS in error. We suspect that it stems from Holmstedt 's analys is of Epena claimed by Seitz to have originated from Virola. This is the lone claim of bufotenine in the genus and it is considered by most not to represent a Virola based snuff for this reason. We encountered one string of claims of bufotenine showing up as a minor base in analysis of this plant (Kawanishi et al. 1985 made the claim for this species citing Schultes & Holmstedt 1971 . Schultes & Holmstedt mention this in passing as part of an included quote taken from Corothie & Nakano 1969. Schultes & Holmstedt deliberately deleted the portion of the quote that implied that Holmstedt found this alkaloid in the species. Holmstedt analyzed epena snuff. Corothie & Nakano 1969's wording could be taken to mean that Holmstedt reported this but do not include a
reference (# 14) for the statement. The only paper of Holmstedt (#6 in their list) that they list is Holmstedt's analysis of Seitz's Epena snuff. [i.e. Holmstedt 1965). At no point during that particular study did Holmstedt analyze plant material of Virola sebifcra and detect this compound. Ref Trout's Notes
Humans and other animals
Coral
Paramuricea chamaeleon (Coral)
- 10 mg. of bufotenine isolated from 200 grams of coral Cimino & DeStefano 1978 ref Trout's Notes
Toads and frogs
(ref Trout's Notes)
- Names followed by plus sign(s) from Daly & Witkop 1971:
- + 1- 100 ug / gm of skin
- ++ 100- 1000 ug / gm. of skin
- +++ 1-10 mg / gm. of skin
Wieland et al 1934 and Wieland& Wieland 1937 Ch'an Su (Chinese phanmceutical preparation of toad venom) Isolated by Jensen & Chen 1932
Bufo sp. Wieland & wieland 1937
Bufo alvarius Wieland & Wieland 1937
- Cutaneous glands were found to contain 0.8 to 5 mg/gm.
- Non-glandular skin was found to contain 0.33-2.15 mg/gm Erspamer et al. 1965
- Up to 3 mg per gram of dried skin.
- Concentrations ranged from less than 0.1 mg to 5.0 mg per gram of large cutaneous glands (averaging 1.2 milligrams/gm. glandular tissue) and from 0.17-2.2 mg per gram (averaging 0.9 mg/ gram) in the rest of the dry skin. Erspamer et al 1967
- + Identified by Erspamer 1954 (Also listed in Erspamer 1961)
- +++ Isolated by Jensen & Chen 1932. Wieland et al. 1934 recovered 5.1 mg/g dried skin. (Also listed inErspamer 1961)
- +++
- ++ Isolated by Handovsky 1920. found to contain 510 ug/animals (0.3% in dry secretions. Females: 90 ug/animal (0.33% in dry secretions) by Wieland & Behringer 1941 . (Also listed in Erspamer 196 1)
- ++
- ++ Identified by Erspamer 1954
- Deulofeu & Rúveda 1971
- + Identified: Alvares Pereira & de Oliveira 1961. Isolated: Deulofeu & Duprat, 1944
- +
- ++
- Isolated by Ohno et al. 1961
- + Identified by Erspamer 1954
Also listed in Erspamer 1961
- +
- ++
- +
- +
- ++
- + (Despite the unsupported claims that this species is a good source of bufotenine, it possesses only low concentrations WHEN it is even present. For example: Cei et al. 1968 found it was present in only some collections and even when present it was sometimes only in some individuals.)
- ++
- +
- +
- +++ Isolated by Deulofeu & Mendive 1938 & by Deulofeu & Duprat 1944
- +++
- +
- ++
- ++
- +
- ++
- +++ Identified by Erspamer 1959, who found 630 ug/gm of dried skin (0.06% in fresh skin.). (Also in Erspamer 1961: 640 ug/ gm of fresh skin.)
- Isolated: Jensen & Chen 1932 & 1936
- (also see Bufo bufo bufo) Handovsky 1920 (Also even earlier by Phisalix & Bertrand 1893 but they did
not fully characterize.) lsolated by Jensen & Chen 1936.
- (0 & 100 ug/ gm: Roseghini et al 1976)
- (0 & 20 ug/ grm: Roseghini et al 1976)
- ++ (0.75 mg/ grn: Roseghini et al. 1976)
- (0.87 & 2.3 mg/ gm: Roseghini et al. 1976)
- + (25 ug/ gm: Roseghini et al. 1976)
- + (5 ug/ gm: Roseghini et al. 1976)
- + (0 & 0 & 8 ug / gm: Roseghini el al. 1976)
- +++ (0.75-7 mg / gm: Roseghini et al 1976)
- + (10 & 15 ug/gm: Roseghini et al. 1976)
- + (10 & 60 ug/ gm: Roseghini et al 1976)
- (35 ug / grm: Roseghini et al. 1976)
- +++
- +
- (85 ug / gm: Roseghini et at. 1976)
- (10-25 ug/ gm: Roseghin.i et al. 1986)
- +
Humans
(ref Trout's Notes)
- Bufotenine is found in normal human blood and urine; Franzen & Gross 1965
- Angrist et a/. 1976 found that while the overall values were higher in their patient group (especially patients with acute psychosis, in women patients and in those patients with a high suspiciousness rating), there was no statistically significant difference between bufotenine blood levels of psychotic patients and normal subjects.
- Karkkainen & Raisanen 1992 also detected endogenous bufotenine in normal humans. See also Raisanen & Karkkainen 1979.
- Narasimhachari et al. 1971b reported it was more common in psychotics than normals; also see Sitaram's papers.
- For more references on its reported occurrences in humans: See Davis 1989.
