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

Template:Align="right" cellspacing="3" style="border: 1px solid | Chemical Properties

2D Structure

3D Structure

Molecular Formula

C₁₂H₁₆N₂O

Chemical Name

3-(2-dimethylamino-ethyl)-indol-4-ol

3-(2-Dimethylamino-aethyl)-indol-4-ol

3-[2-(dimethylamino)ethyl]-1H-indol-4-ol

Molecular Weight

204.27

Melting Point¹

434.15K

pKa Value³

10.01±0.40

Smiles⁵

OC1=CC=CC2=C1C(CCN(C)C)=CN2

CASNo⁵

520-53-6

Psilocin and its congener psilocybin are both found within certain types of fungi known as Psilocybes.

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

UV Spectral Information⁴

Solvent	Methanol
Absorption Maxima	268 nm
	284.5 nm
	294 nm

Synthesis

Psilocin can be synthesised from the readily available 4-hydroxyindole. The mechanism⁴ is detailed below.

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 psychoactive properties of psilocin are a result of its interference with the action of Serotonin in the brain.

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