ChemWiki - User contributions [en]

It:Psilocin

2006-12-08T11:30:28Z

Cpw105:

=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
|-
| colspan="1" | '''Smiles5'''
| colspan="2" | <nowiki>OC1=CC=CC2=C1C(CCN(C)C)=CN2</nowiki>
|-
| colspan="1" | '''CASNo5'''
| colspan="2" | 520-53-6
|}

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]]
 

When psilocybin is ingested into the body, it is metabolised in vivo into psilocin.

=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 [[It:Serotonin|Serotonin]]. It is believed that psychoactive properties of psilocin are a result of its interference with the action of [[It:Serotonin|Serotonin]] in the brain.

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

=Toxicity=
For obvious reasons the toxicity of Psilocin has not been tested on humans however tests have been run on animals specifically rabbits and rats using Psilocybin for the former the LD50 (amount required to kill half of the test population) is 12.5mg/kg in the latter it is 280mg/kg which is greater than caffeine. There have been no documented cases of fatality from Psilocybin at recreational levels.

=Side Effects=
Desirable side effects of psilocin are its hallucinogenic properties however this can have a negative effect i.e. from a 'bad trip' other effects include increased heart rate and blood pressure also nausea, vomiting and stomach pains. There is no reported evidence of withdrawal symtoms or physical dependence

=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
 
5. From www.wikipedia.org

It:Psilocin

2006-12-08T11:19:06Z

Cpw105:

=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
|-
| colspan="1" | '''Smiles5'''
| colspan="2" | <nowiki>OC1=CC=CC2=C1C(CCN(C)C)=CN2</nowiki>
|-
| colspan="1" | '''CASNo5'''
| colspan="2" | 520-53-6
|}

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]]
 

When psilocybin is ingested into the body, it is metabolised in vivo into psilocin.

=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 [[It:Serotonin|Serotonin]]. It is believed that psychoactive properties of psilocin are a result of its interference with the action of [[It:Serotonin|Serotonin]] in the brain.

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

=Toxicity=
For obvious reasons the toxicity of Psilocin has not been tested on humans however tests have been run on animals specifically rabbits and rats using Psilocybin for the former the LD50 (amount required to kill half of the test population) is 12.5mg/kg in the latter it is 280mg/kg which is greater than caffeine. There have been no documented cases of fatality from Psilocybin at recreational levels.

=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
 
5. From www.wikipedia.org

It:Psilocin

2006-12-08T10:53:31Z

Cpw105: /* References */

=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
|-
| colspan="1" | '''Smiles5'''
| colspan="2" | <nowiki>OC1=CC=CC2=C1C(CCN(C)C)=CN2</nowiki>
|-
| colspan="1" | '''CASNo5'''
| colspan="2" | 520-53-6
|}

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]]
 

When psilocybin is ingested into the body, it is metabolised in vivo into psilocin.

=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 [[It:Serotonin|Serotonin]]. It is believed that psychoactive properties of psilocin are a result of its interference with the action of [[It:Serotonin|Serotonin]] in the brain.

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

=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
 
5. From www.wikipedia.org

It:Psilocin

2006-12-08T10:51:32Z

Cpw105:

=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
|-
| colspan="1" | '''Smiles5'''
| colspan="2" | <nowiki>OC1=CC=CC2=C1C(CCN(C)C)=CN2</nowiki>
|-
| colspan="1" | '''CASNo5'''
| colspan="2" | 520-53-6
|}

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]]
 

When psilocybin is ingested into the body, it is metabolised in vivo into psilocin.

=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 [[It:Serotonin|Serotonin]]. It is believed that psychoactive properties of psilocin are a result of its interference with the action of [[It:Serotonin|Serotonin]] in the brain.

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

=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

It:Psilocin

2006-12-08T10:47:54Z

Cpw105: /* Structure and Properties */

=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
|-
| colspan="1" | '''Smiles3'''
| colspan="2" | |<nowiki>OC1=CC=CC2=C1C(CCN(C)C)=CN2</nowiki>
|}

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]]
 

When psilocybin is ingested into the body, it is metabolised in vivo into psilocin.

=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 [[It:Serotonin|Serotonin]]. It is believed that psychoactive properties of psilocin are a result of its interference with the action of [[It:Serotonin|Serotonin]] in the brain.

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

=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