=Psilocin=

Psilocin is a heterocyclic mushroom alkaloid. It is the hallucinogenically active constituent of the class A drug Psilcybe Semilanceata (commonly known as 'Magic Mushrooms').

=Structure and Properties=

{| border="5"

| {{align="right" cellspacing="3" style="border: 1px solid #C0C090; background-color: #F8EABA; margin-bottom: 3px;" colspan="3" }} | Chemical Properties
|-
| colspan="1" | '''2D Structure'''
| colspan="2" | [[Image:Psilocin.gif|thumb|left|400|Structure of Psilocin]]
|-
| colspan="1" | '''3D Structure'''
| colspan="2" | <jmol>
<jmolApplet>
<size>350</size>
<color>black</color>
<script>zoom 100; cpk off;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<inlineContents>HEADER CSD ENTRY XICKAV
CRYST1 8.5594 6.0337 11.0220 90.00 105.97 90.00 P21/c
SCALE1 0.116831 -0.000000 0.033428 0.000000
SCALE2 -0.000000 0.165736 -0.000000 0.000000
SCALE3 -0.000000 0.000000 0.094368 0.000000
ATOM 1 C UNK 0 -3.739 0.735 0.201 0.00 0.00
ATOM 2 C UNK 0 -3.739 -0.602 0.201 0.00 0.00
ATOM 3 C UNK 0 -2.581 -1.271 0.201 0.00 0.00
ATOM 4 C UNK 0 -1.423 -0.602 0.201 0.00 0.00
ATOM 5 C UNK 0 -1.423 0.735 0.201 0.00 0.00
ATOM 6 C UNK 0 -2.581 1.403 0.201 0.00 0.00
ATOM 7 C UNK 0 -1.145 -2.784 0.182 0.00 0.00
ATOM 8 C UNK 0 -0.384 -1.444 0.190 0.00 0.00
ATOM 9 C UNK 0 1.087 -1.165 0.185 0.00 0.00
ATOM 10 C UNK 0 1.319 0.340 0.167 0.00 0.00
ATOM 11 C UNK 0 3.329 0.017 -1.005 0.00 0.00
ATOM 12 C UNK 0 2.950 2.028 0.145 0.00 0.00
ATOM 13 H UNK 0 -4.691 1.285 0.201 0.00 0.00
ATOM 14 H UNK 0 -4.691 -1.152 0.201 0.00 0.00
ATOM 15 H UNK 0 -2.581 2.503 0.201 0.00 0.00
ATOM 16 H UNK 0 -3.145 -3.244 0.188 0.00 0.00
ATOM 17 H UNK 0 -0.693 -3.788 0.172 0.00 0.00
ATOM 18 H UNK 0 1.549 -1.601 1.099 0.00 0.00
ATOM 19 H UNK 0 1.548 -1.623 -0.719 0.00 0.00
ATOM 20 H UNK 0 0.857 0.775 -0.747 0.00 0.00
ATOM 21 H UNK 0 0.858 0.797 1.071 0.00 0.00
ATOM 22 H UNK 0 4.099 -0.724 -0.694 0.00 0.00
ATOM 23 H UNK 0 3.806 0.813 -1.619 0.00 0.00
ATOM 24 H UNK 0 2.543 -0.495 -1.604 0.00 0.00
ATOM 25 H UNK 0 3.526 2.327 1.050 0.00 0.00
ATOM 26 H UNK 0 3.525 2.304 -0.767 0.00 0.00
ATOM 27 H UNK 0 1.969 2.554 0.140 0.00 0.00
ATOM 28 H UNK 0 -0.250 2.384 0.201 0.00 0.00
ATOM 29 N UNK 0 -2.383 -2.521 0.190 0.00 0.00
ATOM 30 N UNK 0 2.732 0.607 0.163 0.00 0.00
ATOM 31 O UNK 0 -0.250 1.412 0.201 0.00 0.00
TER
MASTER 0 0 0 0 0 0 0 0 3 14 0 14 0
END</inlineContents>
</jmolApplet>
</jmol>
|-
| colspan="1" | '''Molecular Formula'''
| colspan="2" | C12H16N2O
|-
| colspan="1" | '''Chemical Name'''
| colspan="2" | 3-(2-dimethylamino-ethyl)-indol-4-ol
|-
| colspan="1" |
| colspan="2" | 3-(2-Dimethylamino-aethyl)-indol-4-ol
|-
| colspan="1" |
| colspan="2" | 3-[2-(dimethylamino)ethyl]-1H-indol-4-ol
|-
| colspan="1" | '''Molecular Weight'''
| colspan="2" | 204.27
|-
| colspan="1" | '''Melting Point1'''
| colspan="2" | 434.15K
|-
| colspan="1" | '''pKa Value3'''
| colspan="2" | 10.01±0.40
|}

Psilocin and its congener psilocybin are both found within certain types of fungi known as Psilocybes.[[Image:Psilocybin.gif|thumb|left|400|Structure of Psilocybin]]
 

=Characterisation=

===13C NMR Spectrum2===

Solvent: Chloroform-d (865-49-6)
 
Spectrometer/Frequency: 400 MHz
[[Image:Sdimg1003731.jpg|left|400|NMR of Psilocin]]
 

===UV Spectral Information4===

{|border="5"

| colspan="1" | '''Solvent'''
| colspan="2" | Methanol
|-
| colspan="1" | '''Absorption Maxima'''
| colspan="2" | 268 nm
|-
| colspan="1" |
| colspan="2" | 284.5 nm
|-
| colspan="1" |
| colspan="2" | 294 nm
|}

=Synthesis=

Psilocin can be synthesised from the readily available 4-hydroxyindole. The mechanism4 is detailed below.[[Image:4-hydroxyindole.gif |thumb|right|400|4-hydroxyindole]]

[[Image:Synthesis of psilocin.gif|left|400|Synthesis of Psilocin (c) 2006 American Chemical Society]]
 
Reagent and conditions: (i) Ac2O, pyridine, CH2Cl2, 0 C to rt; (ii) (COCl)2, ether, 0 C, n-hexane, then -20 C; (iii) (CH3)2NH, THF; (iv) LiAlH4, THF, ; (v) [(BnO)2PO]2O, n-BuLi, THF, -78 C to 0 C; (vi) H2, Pd/C, MeOH, rt.

=Psychoactivity=
Psilocin displays a strong structural similarity to the neurotransmitter serotonin. It is believed that psilocin has psychoactive properties because it interferes with the action of serotonin in the brain.

[[Image:Serotonin.gif|left|400|Synthesis of Serotonin]]

=References=
1. Journal; Kuhnert-Brandstaetter; Heindl; ARPMAS; Arch. Pharm. (Weinheim Ger.); 309; 1976; 625, 627, 628
 
2. Spectral data are provided by Wiley Subscription Services, Inc. (US)
 
3. Calculated using Advanced Chemistry Development (ACD/Labs) Software V8.14 for Solaris (Ó 1994-2006 ACD/Labs)
 
4. Journal; Shirota, Osamu; Hakamata, Wataru; Goda, Yukihiro; JNPRDF; J. Nat. Prod.; EN; 66; 6; 2003; 885 - 887

2006-11-15T19:46:24Z

Fo105:

It:Psilocin

2006-11-15T19:45:33Z

Fo105: /* Synthesis */

=Psilocin=

Psilocin is a heterocyclic mushroom alkaloid. It is the hallucinogenically active constituent of the class A drug Psilcybe Semilanceata (commonly known as 'Magic Mushrooms').

=Structure and Properties=

{| border="5"

| {{align="right" cellspacing="3" style="border: 1px solid #C0C090; background-color: #F8EABA; margin-bottom: 3px;" colspan="3" }} | Chemical Properties
|-
| colspan="1" | '''2D Structure'''
| colspan="2" | [[Image:Psilocin.gif|thumb|left|400|Structure of Psilocin]]
|-
| colspan="1" | '''3D Structure'''
| colspan="2" | <jmol>
<jmolApplet>
<size>350</size>
<color>black</color>
<script>zoom 100; cpk off;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<inlineContents>HEADER CSD ENTRY XICKAV
CRYST1 8.5594 6.0337 11.0220 90.00 105.97 90.00 P21/c
SCALE1 0.116831 -0.000000 0.033428 0.000000
SCALE2 -0.000000 0.165736 -0.000000 0.000000
SCALE3 -0.000000 0.000000 0.094368 0.000000
ATOM 1 C UNK 0 -3.739 0.735 0.201 0.00 0.00
ATOM 2 C UNK 0 -3.739 -0.602 0.201 0.00 0.00
ATOM 3 C UNK 0 -2.581 -1.271 0.201 0.00 0.00
ATOM 4 C UNK 0 -1.423 -0.602 0.201 0.00 0.00
ATOM 5 C UNK 0 -1.423 0.735 0.201 0.00 0.00
ATOM 6 C UNK 0 -2.581 1.403 0.201 0.00 0.00
ATOM 7 C UNK 0 -1.145 -2.784 0.182 0.00 0.00
ATOM 8 C UNK 0 -0.384 -1.444 0.190 0.00 0.00
ATOM 9 C UNK 0 1.087 -1.165 0.185 0.00 0.00
ATOM 10 C UNK 0 1.319 0.340 0.167 0.00 0.00
ATOM 11 C UNK 0 3.329 0.017 -1.005 0.00 0.00
ATOM 12 C UNK 0 2.950 2.028 0.145 0.00 0.00
ATOM 13 H UNK 0 -4.691 1.285 0.201 0.00 0.00
ATOM 14 H UNK 0 -4.691 -1.152 0.201 0.00 0.00
ATOM 15 H UNK 0 -2.581 2.503 0.201 0.00 0.00
ATOM 16 H UNK 0 -3.145 -3.244 0.188 0.00 0.00
ATOM 17 H UNK 0 -0.693 -3.788 0.172 0.00 0.00
ATOM 18 H UNK 0 1.549 -1.601 1.099 0.00 0.00
ATOM 19 H UNK 0 1.548 -1.623 -0.719 0.00 0.00
ATOM 20 H UNK 0 0.857 0.775 -0.747 0.00 0.00
ATOM 21 H UNK 0 0.858 0.797 1.071 0.00 0.00
ATOM 22 H UNK 0 4.099 -0.724 -0.694 0.00 0.00
ATOM 23 H UNK 0 3.806 0.813 -1.619 0.00 0.00
ATOM 24 H UNK 0 2.543 -0.495 -1.604 0.00 0.00
ATOM 25 H UNK 0 3.526 2.327 1.050 0.00 0.00
ATOM 26 H UNK 0 3.525 2.304 -0.767 0.00 0.00
ATOM 27 H UNK 0 1.969 2.554 0.140 0.00 0.00
ATOM 28 H UNK 0 -0.250 2.384 0.201 0.00 0.00
ATOM 29 N UNK 0 -2.383 -2.521 0.190 0.00 0.00
ATOM 30 N UNK 0 2.732 0.607 0.163 0.00 0.00
ATOM 31 O UNK 0 -0.250 1.412 0.201 0.00 0.00
TER
MASTER 0 0 0 0 0 0 0 0 3 14 0 14 0
END</inlineContents>
</jmolApplet>
</jmol>
|-
| colspan="1" | '''Molecular Formula'''
| colspan="2" | C12H16N2O
|-
| colspan="1" | '''Chemical Name'''
| colspan="2" | 3-(2-dimethylamino-ethyl)-indol-4-ol
|-
| colspan="1" |
| colspan="2" | 3-(2-Dimethylamino-aethyl)-indol-4-ol
|-
| colspan="1" |
| colspan="2" | 3-[2-(dimethylamino)ethyl]-1H-indol-4-ol
|-
| colspan="1" | '''Molecular Weight'''
| colspan="2" | 204.27
|-
| colspan="1" | '''Melting Point1'''
| colspan="2" | 434.15K
|-
| colspan="1" | '''pKa Value3'''
| colspan="2" | 10.01±0.40
|}

Psilocin and its congener psilocybin are both found within certain types of fungi known as Psilocybes.[[Image:Psilocybin.gif|thumb|left|400|Structure of Psilocybin]]
 

=Characterisation=

===13C NMR Spectrum2===

Solvent: Chloroform-d (865-49-6)
 
Spectrometer/Frequency: 400 MHz
[[Image:Sdimg1003731.jpg|left|400|NMR of Psilocin]]
 

=Synthesis=

Psilocin can be synthesised from the readily available 4-hydroxyindole. The mechanism is detailed below.[[Image:4-hydroxyindole.gif |thumb|right|400|4-hydroxyindole]]

=Psychoactivity=

=References=
1. Journal; Kuhnert-Brandstaetter; Heindl; ARPMAS; Arch. Pharm. (Weinheim Ger.); 309; 1976; 625, 627, 628
 
2. Spectral data are provided by Wiley Subscription Services, Inc. (US)
 
3. Calculated using Advanced Chemistry Development (ACD/Labs) Software V8.14 for Solaris (Ó 1994-2006 ACD/Labs)

It:Psilocin

2006-11-15T19:45:03Z

Fo105: /* Synthesis */

=Psilocin=

Psilocin is a heterocyclic mushroom alkaloid. It is the hallucinogenically active constituent of the class A drug Psilcybe Semilanceata (commonly known as 'Magic Mushrooms').

=Structure and Properties=

{| border="5"

| {{align="right" cellspacing="3" style="border: 1px solid #C0C090; background-color: #F8EABA; margin-bottom: 3px;" colspan="3" }} | Chemical Properties
|-
| colspan="1" | '''2D Structure'''
| colspan="2" | [[Image:Psilocin.gif|thumb|left|400|Structure of Psilocin]]
|-
| colspan="1" | '''3D Structure'''
| colspan="2" | <jmol>
<jmolApplet>
<size>350</size>
<color>black</color>
<script>zoom 100; cpk off;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<inlineContents>HEADER CSD ENTRY XICKAV
CRYST1 8.5594 6.0337 11.0220 90.00 105.97 90.00 P21/c
SCALE1 0.116831 -0.000000 0.033428 0.000000
SCALE2 -0.000000 0.165736 -0.000000 0.000000
SCALE3 -0.000000 0.000000 0.094368 0.000000
ATOM 1 C UNK 0 -3.739 0.735 0.201 0.00 0.00
ATOM 2 C UNK 0 -3.739 -0.602 0.201 0.00 0.00
ATOM 3 C UNK 0 -2.581 -1.271 0.201 0.00 0.00
ATOM 4 C UNK 0 -1.423 -0.602 0.201 0.00 0.00
ATOM 5 C UNK 0 -1.423 0.735 0.201 0.00 0.00
ATOM 6 C UNK 0 -2.581 1.403 0.201 0.00 0.00
ATOM 7 C UNK 0 -1.145 -2.784 0.182 0.00 0.00
ATOM 8 C UNK 0 -0.384 -1.444 0.190 0.00 0.00
ATOM 9 C UNK 0 1.087 -1.165 0.185 0.00 0.00
ATOM 10 C UNK 0 1.319 0.340 0.167 0.00 0.00
ATOM 11 C UNK 0 3.329 0.017 -1.005 0.00 0.00
ATOM 12 C UNK 0 2.950 2.028 0.145 0.00 0.00
ATOM 13 H UNK 0 -4.691 1.285 0.201 0.00 0.00
ATOM 14 H UNK 0 -4.691 -1.152 0.201 0.00 0.00
ATOM 15 H UNK 0 -2.581 2.503 0.201 0.00 0.00
ATOM 16 H UNK 0 -3.145 -3.244 0.188 0.00 0.00
ATOM 17 H UNK 0 -0.693 -3.788 0.172 0.00 0.00
ATOM 18 H UNK 0 1.549 -1.601 1.099 0.00 0.00
ATOM 19 H UNK 0 1.548 -1.623 -0.719 0.00 0.00
ATOM 20 H UNK 0 0.857 0.775 -0.747 0.00 0.00
ATOM 21 H UNK 0 0.858 0.797 1.071 0.00 0.00
ATOM 22 H UNK 0 4.099 -0.724 -0.694 0.00 0.00
ATOM 23 H UNK 0 3.806 0.813 -1.619 0.00 0.00
ATOM 24 H UNK 0 2.543 -0.495 -1.604 0.00 0.00
ATOM 25 H UNK 0 3.526 2.327 1.050 0.00 0.00
ATOM 26 H UNK 0 3.525 2.304 -0.767 0.00 0.00
ATOM 27 H UNK 0 1.969 2.554 0.140 0.00 0.00
ATOM 28 H UNK 0 -0.250 2.384 0.201 0.00 0.00
ATOM 29 N UNK 0 -2.383 -2.521 0.190 0.00 0.00
ATOM 30 N UNK 0 2.732 0.607 0.163 0.00 0.00
ATOM 31 O UNK 0 -0.250 1.412 0.201 0.00 0.00
TER
MASTER 0 0 0 0 0 0 0 0 3 14 0 14 0
END</inlineContents>
</jmolApplet>
</jmol>
|-
| colspan="1" | '''Molecular Formula'''
| colspan="2" | C12H16N2O
|-
| colspan="1" | '''Chemical Name'''
| colspan="2" | 3-(2-dimethylamino-ethyl)-indol-4-ol
|-
| colspan="1" |
| colspan="2" | 3-(2-Dimethylamino-aethyl)-indol-4-ol
|-
| colspan="1" |
| colspan="2" | 3-[2-(dimethylamino)ethyl]-1H-indol-4-ol
|-
| colspan="1" | '''Molecular Weight'''
| colspan="2" | 204.27
|-
| colspan="1" | '''Melting Point1'''
| colspan="2" | 434.15K
|-
| colspan="1" | '''pKa Value3'''
| colspan="2" | 10.01±0.40
|}

Psilocin and its congener psilocybin are both found within certain types of fungi known as Psilocybes.[[Image:Psilocybin.gif|thumb|left|400|Structure of Psilocybin]]
 

=Characterisation=

===13C NMR Spectrum2===

Solvent: Chloroform-d (865-49-6)
 
Spectrometer/Frequency: 400 MHz
[[Image:Sdimg1003731.jpg|left|400|NMR of Psilocin]]
 

=Synthesis=

Psilocin can be synthesised from 4-hydroxyindole. The mechanism is detailed below.[[Image:4-hydroxyindole.gif |thumb|right|400|4-hydroxyindole]]

=Psychoactivity=

=References=
1. Journal; Kuhnert-Brandstaetter; Heindl; ARPMAS; Arch. Pharm. (Weinheim Ger.); 309; 1976; 625, 627, 628
 
2. Spectral data are provided by Wiley Subscription Services, Inc. (US)
 
3. Calculated using Advanced Chemistry Development (ACD/Labs) Software V8.14 for Solaris (Ó 1994-2006 ACD/Labs)

File:4-hydroxyindole.gif

2006-11-15T19:44:29Z

Fo105:

2006-11-06T16:05:05Z

Fo105:

It:Psilocin

2006-11-06T16:02:43Z

Fo105: /* Structure and Properties */

2006-11-06T15:40:25Z

Fo105: /* NMR Spectrum2 */

=Psilocin=

Psilocin is a heterocyclic mushroom alkaloid. It is the hallucinogenically active constituent of the class A drug Psilcybe Semilanceata (commonly known as 'Magic Mushrooms').
=Structure and Properties=

[[Image:Psilocin.gif|thumb|left|400|Structure of Psilocin]]

{| border="5"

| {{align="right" cellspacing="3" style="border: 1px solid #C0C090; background-color: #F8EABA; margin-bottom: 3px;" colspan="2" }} | Chemical Properties
|-
| colspan="1" | '''Molecular Formula'''
| colspan="2" | C12H16N2O
|-
| colspan="1" | '''Chemical Name'''
| colspan="2" | 3-(2-dimethylamino-ethyl)-indol-4-ol
|-
| colspan="1" |
| colspan="2" | 3-(2-Dimethylamino-aethyl)-indol-4-ol
|-
| colspan="1" |
| colspan="2" | 3-[2-(dimethylamino)ethyl]-1H-indol-4-ol
|-
| colspan="1" | '''Molecular Weight'''
| colspan="2" | 204.27
|-
| colspan="1" | '''Melting Point'''
| colspan="2" | 434.15K1
|}

<jmol>
<jmolApplet>
<size>350</size>
<color>black</color>
<script>zoom 100; cpk off;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<inlineContents>HEADER CSD ENTRY XICKAV
CRYST1 8.5594 6.0337 11.0220 90.00 105.97 90.00 P21/c
SCALE1 0.116831 -0.000000 0.033428 0.000000
SCALE2 -0.000000 0.165736 -0.000000 0.000000
SCALE3 -0.000000 0.000000 0.094368 0.000000
ATOM 1 C UNK 0 -3.739 0.735 0.201 0.00 0.00
ATOM 2 C UNK 0 -3.739 -0.602 0.201 0.00 0.00
ATOM 3 C UNK 0 -2.581 -1.271 0.201 0.00 0.00
ATOM 4 C UNK 0 -1.423 -0.602 0.201 0.00 0.00
ATOM 5 C UNK 0 -1.423 0.735 0.201 0.00 0.00
ATOM 6 C UNK 0 -2.581 1.403 0.201 0.00 0.00
ATOM 7 C UNK 0 -1.145 -2.784 0.182 0.00 0.00
ATOM 8 C UNK 0 -0.384 -1.444 0.190 0.00 0.00
ATOM 9 C UNK 0 1.087 -1.165 0.185 0.00 0.00
ATOM 10 C UNK 0 1.319 0.340 0.167 0.00 0.00
ATOM 11 C UNK 0 3.329 0.017 -1.005 0.00 0.00
ATOM 12 C UNK 0 2.950 2.028 0.145 0.00 0.00
ATOM 13 H UNK 0 -4.691 1.285 0.201 0.00 0.00
ATOM 14 H UNK 0 -4.691 -1.152 0.201 0.00 0.00
ATOM 15 H UNK 0 -2.581 2.503 0.201 0.00 0.00
ATOM 16 H UNK 0 -3.145 -3.244 0.188 0.00 0.00
ATOM 17 H UNK 0 -0.693 -3.788 0.172 0.00 0.00
ATOM 18 H UNK 0 1.549 -1.601 1.099 0.00 0.00
ATOM 19 H UNK 0 1.548 -1.623 -0.719 0.00 0.00
ATOM 20 H UNK 0 0.857 0.775 -0.747 0.00 0.00
ATOM 21 H UNK 0 0.858 0.797 1.071 0.00 0.00
ATOM 22 H UNK 0 4.099 -0.724 -0.694 0.00 0.00
ATOM 23 H UNK 0 3.806 0.813 -1.619 0.00 0.00
ATOM 24 H UNK 0 2.543 -0.495 -1.604 0.00 0.00
ATOM 25 H UNK 0 3.526 2.327 1.050 0.00 0.00
ATOM 26 H UNK 0 3.525 2.304 -0.767 0.00 0.00
ATOM 27 H UNK 0 1.969 2.554 0.140 0.00 0.00
ATOM 28 H UNK 0 -0.250 2.384 0.201 0.00 0.00
ATOM 29 N UNK 0 -2.383 -2.521 0.190 0.00 0.00
ATOM 30 N UNK 0 2.732 0.607 0.163 0.00 0.00
ATOM 31 O UNK 0 -0.250 1.412 0.201 0.00 0.00
TER
MASTER 0 0 0 0 0 0 0 0 3 14 0 14 0
END</inlineContents>
</jmolApplet>
</jmol>

Psilocin and its congener psilocybin are both found within certain types of fungi known as Psilocybes.
[[Image:Psilocybin.gif|thumb|left|400|Structure of Psilocybin]]
 

=Characterisation=

==13C NMR Spectrum2==
[[Image:Sdimg1003731.jpg|left|400|NMR of Psilocin]]

Solvent: Chloroform-d (865-49-6)
Spectrometer/Frequency: 400 MHz

=References=
1. Journal; Kuhnert-Brandstaetter; Heindl; ARPMAS; Arch. Pharm. (Weinheim Ger.); 309; 1976; 625, 627, 628
 
2. Spectral data are provided by Wiley Subscription Services, Inc. (US)