Bufotenin
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| Surname | Bufotenin | |||||||||||||||||||||
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| Molecular formula | C 12 H 16 N 2 O | |||||||||||||||||||||
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| Molar mass | 204.27 g · mol -1 | |||||||||||||||||||||
| Physical state |
firmly |
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| density |
1.205 g cm −3 (base) |
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| Melting point |
146-147 ° C |
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| boiling point |
320 ° C |
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| As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions . | ||||||||||||||||||||||
Bufotenin (of Bufo - toad) is a psychedelic effective hallucinogenic tryptamine - alkaloid . Bufotenin is closely related to the human neurotransmitter serotonin and is a structural isomer of the fungal hallucinogen psilocin .
effect
The effect is essentially the same as the very similar psilocin, the breakdown product of psilocybin . Optical hallucinations such as flashes of light occur together with dizziness, high blood pressure and states of confusion. Nausea and tachycardia are also possible.
The hallucinogenic effects have long been considered controversial. The first indications were found in the 1950s. Tests on humans in the following decades did not produce a uniform picture. Since the drug was also administered to the mentally ill and imprisoned against their will, the setting in these cases is likely to have been rather unfavorable. In contrast, there are numerous reports of cultic use (see occurrence). The pure substance plays no role as an intoxicant and is also not used pharmaceutically.
Occurrence
Bufotenin is found naturally in various plants and is one of the few psychoactive drugs that is also obtained from animals. In addition, the substance was found in small quantities in human urine and appears to be a normal breakdown product of human metabolism .
Occurrence in plants
Anadenanthera peregrina
Anadenanthera peregrina is a tree in the legume family . The seeds are dried, roasted and ground into powder. Various South American Indian tribes use this to produce hallucinogenic snuff for generating spiritual experiences . In the Orinoco Basin, the drug is called Yopo and Ebena . In the Caribbean it was known as Cohoba , but is no longer needed there.
Anadenanthera colubrina
Anadenanthera colubrina is closely related to Anadenanthera peregrina. Here, too, the bufotenin-containing seeds are ground up and consumed as snuff. The powder is known by the Indians in Peru and Argentina under the names Vilca or Huilca .
Occurrence in animals
Bufotenin is found in the skin secretion of various toads . The great cane toad ( Bufo marinus ) is of particular cultural and historical significance .
In Veracruz , Mexico , it was used to make a hallucinogenic drink from it, which was used in initiation rites. From Australia in the 1990s there were several reports of the newly emerging custom of toad licking. The poisonous secretion is released by massaging the toad and then licked up. How widespread this custom actually is or to what extent it is a phenomenon exaggerated by the press cannot be said with certainty. In any case, the oral consumption of the secretion is not without risk, since bufotoxin contains cardiac toxins in addition to bufotenin . Their effect is similar to that of digitalis glycosides . To avoid the poisonous effect, the toad secretion is smoked. While the poisonous components of the secretion are supposedly destroyed, the chemically very stable bufotenin should be preserved.
In addition to the cane toad Bufotenin was also observed in the Colorado toad ( Bufo alvarius ), the sand toad ( Bufo arenarum ), the domestic toad ( Bufo bufo ), the toad ( Bufo viridis ) and other Real toads detected.
Other occurrences
Bufotenin was found in small quantities in the yellow cap mushroom , fly agaric , porphyry brown amanita and panther mushroom as well as in the rhizomes of reed .
Legal status
In the USA, Bufotenin is a Schedule I drug and therefore not marketable.
Individual evidence
- ^ R. Bergin, D. Carlström, G. Falkenberg, H. Ringertz: Preliminary X-ray crystallographic study of some psychoactive indole bases in Acta Cryst. B 24 (1968) 882, doi : 10.1107 / S0567740868003353 .
- ↑ TiHKAL entry. Retrieved July 23, 2008 : "The free base has been reported to have a mp of 125-126 ° C or 146-147 ° C" , most current sources give 146-147 ° C.
- ↑ a b NeoShamanic Snuffs. Retrieved July 23, 2008 .
- ↑ a b Bufotenine oxalate salt data sheet from Sigma-Aldrich , accessed on April 27, 2011 ( PDF ).
- ↑ José M. Capriles, Christine Moore, Juan Albarracin-Jordan, Melanie J. Miller: Chemical evidence for the use of multiple psychotropic plants in a 1,000-year-old ritual bundle from South America . In: Proceedings of the National Academy of Sciences . May 1, 2019, ISSN 0027-8424 , p. 201902174 , doi : 10.1073 / pnas.1902174116 , PMID 31061128 ( pnas.org [accessed May 22, 2019]).
- ↑ Melanie J. Miller, Juan Albarracin-Jordan, Christine Moore, and José M. Capriles: Chemical evidence for the use of multiple psychotropic plants in a 1,000-year-old ritual bundle from South America. PNAS, 2019, accessed May 22, 2019 .
- ^ Marc Blainey: Evidence for Ritual Use of Entheogens in Ancient Mesoamerica and the Implications for the Approach to Religion and Worldview , accessed September 22, 2015.
