Psilocin

Structural formula
General
Surname	Psilocin
other names	4-hydroxy- N , N -dimethyltryptamine; 3- [2- (dimethylamino) ethyl] -1 H -indol-4-ol; 4-HO-DMT;
Molecular formula	C 12 H 16 N 2 O
External identifiers / databases
EC number	208-296-5
ECHA InfoCard	100.007.543
PubChem	4980
Wikidata	Q409150
properties
Molar mass	204.27 g mol −1
Physical state	firmly
Melting point	173-176 ° C
solubility	very bad in water
safety instructions
GHS labeling of hazardous substances Caution
H and P phrases	H: 302
	P: no P-phrases
Toxicological data	7 mg kg −1 ( LD 50 , rabbit , iv )
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Psilocin is an indole alkaloid and one of the tryptamines . It is the hydrolysis product of psilocybin and thus represents the actually psychoactive form of psilocybin. In addition, it also occurs as an alkaloid itself . The free base decomposes in air.

It is often used as an intoxicant because of its hallucinogenic effects . The effects of ingestion are similar to those of an LSD intoxication, but they are usually shorter in duration. Psilocin is usually consumed in the form of mushrooms containing psilocybin .

history

Albert Hofmann and his laboratory assistant Hans Tscherter at Sandoz isolated psilocin and its phosphate ester psilocybin from hallucinogenic mushrooms in 1959 . In the 1960s, studies and psycholytic therapy with psilocin were carried out, especially in the psychiatric field , until these came to a standstill due to strict regulations. At the moment, research into psilocin-assisted psychotherapy is intensifying again. a. treatment-resistant depression and end-stage cancer patients, in order to enable them to possibly better deal with death.

chemistry

Psilocin results from the dephosphorylation of psilocybin , e.g. B. under strongly acidic or alkaline conditions. Psilocin is relatively unstable because of its phenolic OH group.

Under alkaline conditions and in the presence of oxygen, it immediately forms bluish degradation products. Similar products are also produced under acidic conditions, in the presence of oxygen and iron (III) ions ( Keller reagent FeCl ₃ / MeOH / HCl).

Psilocin is a basic amine . Its salts, which it z. B. can form with acids are usually more stable than psilocin.

pharmacology

Psilocin is a partial agonist at the 5-HT _2A receptor . Its binding profile (as far as is known) is less complex than that of LSD. The binding of psilocin to the 5-HT _2C receptor is probably responsible for side effects (e.g. on the blood sugar level). O -acetylpsilocin and psilocybin are believed to be prodrugs of psilocin.

Side effects of consumption

Cases of persistent perception disorders after hallucinogen use ( hallucinogen persisting perception disorder , HPPD) are known. In extreme cases, drug psychosis can be triggered, as Espiard showed in a monocasuistic study.

toxicity

The ratio of effective dose to lethal dose differs widely in comparison to other psychoactive substances. If the psilocin were consumed in the form of fresh mushrooms, the dose for physiologically fatal poisoning would be around 1 kg mushrooms / kg body weight.

Legal position

Germany

With the fourth Narcotics Equal Opportunities Ordinance (4th BtMGlV) of February 21, 1967, which came into force on February 25, 1967, psilocybin and psilocin in the Federal Republic of Germany were made subject to the narcotics regulations of the Opium Act . Today psilocybin and psilocin are listed in Appendix I to Section 1 of the BtMG (substances that are not marketable or prescription-free). The acquisition, possession and distribution of these substances is therefore generally prohibited.

Web links

TIHKAL: Psilocin (English)

Individual evidence

↑ Entry on psilocybin. In: Römpp Online . Georg Thieme Verlag, accessed on May 30, 2014.
^ The Merck Index . An Encyclopaedia of Chemicals, Drugs and Biologicals . 14th edition, 2006, p. 1363, ISBN 978-0-911910-00-1 .
↑ ^a ^b ^c data sheet Psilocin from Sigma-Aldrich , accessed on April 22, 2011 ( PDF ).
↑ Deutscher Ärzteverlag GmbH, editor of the Deutsches Ärzteblatt: Cancer: Fungal hallucinogen relieves depression and takes away fear of ... ( aerzteblatt.de [accessed on September 22, 2018]).
^ Robin L Carhart-Harris, Leor Roseman, Mark Bolstridge, Lysia Demetriou, J Nienke Pannekoek: Psilocybin for treatment-resistant depression: fMRI-measured brain mechanisms . In: Scientific Reports . tape 7 , no. 1 , October 13, 2017, ISSN 2045-2322 , doi : 10.1038 / s41598-017-13282-7 ( nature.com [accessed September 22, 2018]).
↑ FDA approves magic mushrooms depression drug trial . In: Newsweek . August 23, 2018 ( newsweek.com [accessed September 22, 2018]).
↑ David E. Nichols (2004): Hallucinogens. In: Pharmacol Ther . 101: 131-181, PDF .
↑ ML Espiard et al. a .: Hallucinogen persisting perception disorder after psilocybin consumption: a case study. In: Eur. Psychiatry. Volume 20, Numbers 5-6, 2005. pp. 458-460, PMID 15963699 .
↑ 4th BtMGlV of February 21, 1967 .

[Römpp-1] Entry on psilocybin. In: Römpp Online . Georg Thieme Verlag, accessed on May 30, 2014.

[MerckIndex-2] The Merck Index . An Encyclopaedia of Chemicals, Drugs and Biologicals . 14th edition, 2006, p. 1363, ISBN 978-0-911910-00-1 .

[sigma-aldrich-3] ta sheet Psilocin from Sigma-Aldrich , accessed on April 22, 2011 ( PDF ).

[4] Deutscher Ärzteverlag GmbH, editor of the Deutsches Ärzteblatt: Cancer: Fungal hallucinogen relieves depression and takes away fear of ... ( aerzteblatt.de [accessed on September 22, 2018]).

[5] Robin L Carhart-Harris, Leor Roseman, Mark Bolstridge, Lysia Demetriou, J Nienke Pannekoek: Psilocybin for treatment-resistant depression: fMRI-measured brain mechanisms . In: Scientific Reports . tape 7 , no. 1 , October 13, 2017, ISSN 2045-2322 , doi : 10.1038 / s41598-017-13282-7 ( nature.com [accessed September 22, 2018]).

[6] FDA approves magic mushrooms depression drug trial . In: Newsweek . August 23, 2018 ( newsweek.com [accessed September 22, 2018]).

[7] David E. Nichols (2004): Hallucinogens. In: Pharmacol Ther . 101: 131-181, PDF .

[8] ML Espiard et al. a .: Hallucinogen persisting perception disorder after psilocybin consumption: a case study. In: Eur. Psychiatry. Volume 20, Numbers 5-6, 2005. pp. 458-460, PMID 15963699 .

[9] 4th BtMGlV of February 21, 1967 .