Bufotenin

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Bufotenin
Formula	C12H16N2O
Molecular mass	204.268 g/mol
SMILES	CN(C)CCC1=CNC2=C1C=C(O)C=C2

Bufotenin, also spelled bufotenine and commonly known under the name 5-hydroxy-DMT (5-OH-DMT), is a tryptamine related to the neurotransmitter serotonin. It is an alkaloid "found in frog or toad skins, mushrooms, higher plants, and mammals, especially in the brains, plasma and urine of schizophrenics."^[1] Its name originates from the psychoactive toad Bufo alvarius^[2], which secretes bufotoxins from their parotoid glands.^[3] Bufotenin is a hallucinogenic compound.

Bufotenin is almost identical to the chemical structure of psilocin, another hallucinogen; the only difference is the hydroxyl (OH-) group is moved one place over on the indole ring.

Contents 1 Toads 2 Anadenanthera Seeds 3 References 4 External links

[edit] Toads

The toad was "recurrently depicted in Mesoamerican art," ^[4] suggesting that the effects of ingesting bufosecretion has been known for years; however, some doubt that this art provides sufficient "ethnohistorical evidence" to support this claim. ^[5] The Bufo alvarius toad, because of its hallucinogenic secretion (which primarily contains serotonin, 5-MeO-DMT, bufotenin, bufotenidine, and dehydrobufotenine^[6]), has gained media attention ^[7][8] and been used as a source for recreational drug use. Perhaps the most prominent example of recreational Bufo alvarius use is the story of Albert Most, founder of the Church of the Toad of Light, who published a booklet ^[9] in 1994 explaining how to extract and smoke the secretions, titled Bufo avlarius: The Psychedelic Toad of the Sonoran Desert.

Some severe poisonings were recorded after some toad lickers mistakenly used Bufo marinus (Common Cane Toad) and other species for this purpose.^[specify] The venom of B. marinus contains Bufotenin alongside cardiotoxic steroids, the use of which can lead to heart attacks and death.^[specify]

[edit] Anadenanthera Seeds

Bufotenin is also the primary constituent of Vilca (also known as Cebil) and Yopo (believed by some to be Cohoba) snuffs ^[10], made from beans of the Anadenanthera colubrina and Anadenanthera peregrina trees, respectfully. The use of these seeds have been historically linked to shamans in South America. ^[11]

Cohoba was used by the tribe with whom Christopher Columbus made first contact, the Taino of Cuba and Hispaniola.^[specify] The use of Cohoba snuffs has been documented in the archaeological record for thousands of years, and it has the longest recorded continuous use of any psychoactive plant in the world.^[specify]

[edit] References

1. ^ CID 10257 -- PubChem Compound Summary
2. ^ Ott, Jonathan. 1996. "Pharmacotheon: Entheogenic Drugs, Their Plant Sources and History." Natural Products Co.
3. ^ AmphibiaWeb
4. ^ Kennedy, Alison Bailey. 1982. "Ecce Bufo: The Toad in Nature and in Olmec Iconography." Current Anthropology, 23: 273-290.
5. ^ Davis, Wade and Andrew Weil. 1992. "Identify of a New World Psychoactive Toad." Ancient Mesoamerica, 3: 51-59.
6. ^ The History and Psychoactivity of Bufo Toads
7. ^ NPR: The Dog Who Loved to Suck on Toads
8. ^ Psychoactive toad: Cultural references
9. ^ How ‘bout them toad suckers? Ain’t they clods?
10. ^ Pharmanopo-Psychonautics: Human Intranasal, Sublingual, Intrarectal, Pulmonary and Oral Pharmacology of Bufotenine
11. ^ Ott, Jonathan: "Shamanic Snuffs or Entheogenic Errhines." Entheobotanica, 2001.

[edit] External links

• Erowid's Bufotenin Vault
• The Preparation of Anadenanthera Snuffs (Plot55.com)
• Growing Anadenanthera colubrina (Plot55.com)
• TiHKAL entry on Bufotenin