Bufotoxin

Bufotenin

General
Systematic name	3-(2-Dimethylamino-ethyl)-1H-indol-5-ol
Molecular formula	C₁₂H₁₆N₂O
SMILES	OC1=CC2=C(NC=C2CCN(C)C)C=C1
Molar mass	204.27 gmol^-1
Properties
Melting point	419.65 K ^[1]
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox disclaimer and references

Bufotoxin is a composition of toxins that are used by some toads (genus Bufo). It can be found on the skin of the toads as well as in the venom and the parotoid glands. The toxin consists of a mixture of:

5-MeO-DMT, bufagins, bufotalin, bufotenine, bufothionine, epinephrine, norepinephrine, and serotonin.

The composition of the toxin depends where exactly the toxin comes from. Some plants mushrooms and amphibians also use the toxin.

Bufotenin (also Bufotenine)

Bufotenin (a typtamine alkaloid)is used by some animals for there hallucinogenic ability in a defence system. It is found in mushrooms, some plants, mammals and possibly in bodily fluids of schizophrenics.

3D representation of Bufotenin molecule

3D model of Bufotenin unit cell

Pentahelicene

Spectral data

Infrared spectrum

IR peaks (Nujol): 3620 cm^-1 journal ^[2]

NMR

¹H NMR peaks (D₂O): adapted from journal^[3]

Chemical shift	Splitting multiplicity	Integration	Coupling constant (J/Hz)
2.76	singlet	6H	N\A
2.95	triplet	2H	7.5
3.18	triplet	2H	7.5
6.86	double doublet	1H	8.8, 2.6
7.02	doublet	1H	2.6
7.15	singlet	1H	N\A
7.38	doublet	1H	8.8

Mass Spectrum

Human experience of Bufotenin vapour

After inhaling the fumes from the bufotenin the inital effect is an increased intensity of visuals and and anxiety accompanied by a general increased awareness. The next step in the experience is hallucinating and seeing swirling around the room with sweating. After a while the sweating and anxiety stops and a more relexed atmosphere still with strong hallucinating effects occurs. After a couple of hours the effect wears off into nothing. The effect of the bufotenin can depend on which form the bufotenin is in e.g. calcium bufotenin or bufotenin hydrochloride can have very different effects.^[5]

Serotonin

Serotonin

General
Systematic name	3-(2-aminoethyl)-1H-indol-5-ol
Molecular formula	C₁₀H₁₂N₂O
[1]	5202
[2]	50-67-9
SMILES	OC1=CC=C(NC=C2CCN)C2=C1
Molar mass	176.215 gmol^-1
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox disclaimer and references

3D Representation of Serotonin

Serotonin

Serotonin picrate monohydrate Crystal Unit Cell (C₁₀H₁₃N₂O⁺, C₆H₂N₃O₇^-, H₂O)

Serotonin

References

↑ I. J. Pachter, D. E. Zacharias and O. Ribeiro, J. Org. Chem., 1959, 24, 1285-1287.DOI:10.1021/jo01091a032
↑ G. Revial, I. Jabin, S. Lim and M. Pfau, J. Org. Chem., 2002, 67, 2252-2256.DOI:10.1021/jo0110597
↑ G. Revial, I. Jabin, S. Lim and M. Pfau, J. Org. Chem., 2002, 67, 2252-2256.DOI:10.1021/jo0110597
↑ T. O. G. Costa, R. A. V. Morales, J. P. Brito, M. Gordo, A. C. Pinto and J. C. Bloch, Toxicon, 2005, 46, 371-375. DOI:10.1016/j.toxicon.2005.02.006
↑ Erowid experience vaults:http://www.erowid.org/experiences/exp.php?ID=64707

[1] I. J. Pachter, D. E. Zacharias and O. Ribeiro, J. Org. Chem., 1959, 24, 1285-1287.DOI:10.1021/jo01091a032

[2] G. Revial, I. Jabin, S. Lim and M. Pfau, J. Org. Chem., 2002, 67, 2252-2256.DOI:10.1021/jo0110597

[3] G. Revial, I. Jabin, S. Lim and M. Pfau, J. Org. Chem., 2002, 67, 2252-2256.DOI:10.1021/jo0110597

[4] T. O. G. Costa, R. A. V. Morales, J. P. Brito, M. Gordo, A. C. Pinto and J. C. Bloch, Toxicon, 2005, 46, 371-375. DOI:10.1016/j.toxicon.2005.02.006

[5] Erowid experience vaults:http://www.erowid.org/experiences/exp.php?ID=64707

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