It07:Bufotoxin

2007-10-31T14:50:40Z

Hm206:

=Bufotoxin=

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, [http://www.ch.imperial.ac.uk/wiki/index.php/It07:Epinephrine 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.

''General Information''

Systematic name: 3-(2-Dimethylamino-ethyl)-1''H''-indol-5-ol

Molecular Formula: C<sub>12</sub>H<sub>16</sub>N<sub>2</sub>O

Molecular weight: 204.27 g/mol

Melting point: 146.5 °C <ref>I. J. Pachter, D. E. Zacharias and O. Ribeiro, J. Org. Chem., 1959, 24, 1285-1287.{{DOI|10.1021/jo01091a032}}</ref>

Smile: OC1=CC2=C(NC=C2CCN(C)C)C=C1

[[Image: bufotenin.gif|thumb|right|200|Bufotenin 2D image]]

===3D representation of ''Bufotenin molecule''===

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DSViewer 3D 0

15 16 0 0 0 0 0 0 0 0999 V2000
1.4600 -1.5600 0.0000 C 0 0 0 0 0 0 0 0 0 1
2.4600 -0.7500 0.0000 C 0 0 0 0 0 0 0 0 0 2
0.4700 -0.7500 0.0000 C 0 0 0 0 0 0 0 0 0 3
3.4600 -1.5600 0.0000 N 0 0 0 0 0 0 0 0 0 4
-1.5200 -0.7500 0.0000 C 0 0 0 0 0 0 0 0 0 5
0.4700 0.8500 0.0000 C 0 0 0 0 0 0 0 0 0 6
4.4600 -0.7500 0.0000 C 0 0 0 0 0 0 0 0 0 7
3.4600 -3.1700 0.0000 C 0 0 0 0 0 0 0 0 0 8
-1.5200 0.8500 0.0000 C 0 0 0 0 0 0 0 0 0 9
-2.5100 -1.5600 0.0000 C 0 0 0 0 0 0 0 0 0 10
-0.5200 1.6600 0.0000 N 0 0 0 0 0 0 0 0 0 11
-2.5100 1.6600 0.0000 C 0 0 0 0 0 0 0 0 0 12
-3.5100 -0.7500 0.0000 C 0 0 0 0 0 0 0 0 0 13
-3.5100 0.8500 0.0000 C 0 0 0 0 0 0 0 0 0 14
-4.5100 -1.5600 0.0000 O 0 0 0 0 0 0 0 0 0 15
1 2 1 0 0 0
1 3 1 0 0 0
2 4 1 0 0 0
3 5 1 0 0 0
3 6 2 0 0 0
4 7 1 0 0 0
4 8 1 0 0 0
5 9 2 0 0 0
5 10 1 0 0 0
6 11 1 0 0 0
9 11 1 0 0 0
9 12 1 0 0 0
10 13 2 0 0 0
12 14 2 0 0 0
13 14 1 0 0 0
13 15 1 0 0 0
M END</inlineContents>
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===3D model of Bufotenin unit cell===

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''Infrared spectrum''

IR peaks (Nujol): 3620 cm<sup>-1</sup> [http://pubs.acs.org/cgi-bin/article.cgi/joceah/2002/67/i07/html/jo0110597.html journal] <ref>G. Revial, I. Jabin, S. Lim and M. Pfau, J. Org. Chem., 2002, 67, 2252-2256.{{DOI|10.1021/jo0110597}}</ref>

''NMR''

''<sup>1</sup>H NMR'' peaks (D<sub>2</sub>O): adapted from [http://pubs.acs.org/cgi-bin/article.cgi/joceah/2002/67/i07/html/jo0110597.html journal]<ref>G. Revial, I. Jabin, S. Lim and M. Pfau, J. Org. Chem., 2002, 67, 2252-2256.{{DOI|10.1021/jo0110597}}</ref>

{| class="wikitable"
{| border="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''

[[Image:Bufomass.JPG|thumb|left|Mass spectrum of Bufotenin<ref>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}}</ref>]]

==Human experience of Bufotenin vapour ==

<ref>Erowid experience vaults:http://www.erowid.org/experiences/exp.php?ID=64707</ref>

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.

==Serotonin==

''General Information''

IUPAC Name: 3-(2-aminoethyl)-1H-indol-5-ol

Molecular Formula: C<sub>10</sub>H<sub>12</sub>N<sub>2</sub>O

Molecular weight: 176.215 g/mol

Smile: OC1=CC=C(NC=C2CCN)C2=C1

PubChem: 5202

[[Image:Serotonin.jpg|thumb|right|200|Serotonin Structure]]

3D Representation of ''Serotonin''

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Serotonin picrate monohydrate ''Crystal Unit Cell'' (C<sub>10</sub>H<sub>13</sub>N<sub>2</sub>O<sup>+</sup>, C<sub>6</sub>H<sub>2</sub>N<sub>3</sub>O<sub>7</sub><sup>-</sup>, H<sub>2</sub>O)

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=References=

<references/>