Simple indole alkaloids and those with a nonrearranged monoterpenoid unit

Psilocybin and related hallucinogenic compounds are increasingly used in human research. However, due to limited information about potential subjective side effects, the controlled medical use of these compounds has remained controversial. We therefore analysed acute, short- and long-term subjective effects of psilocybin in healthy humans by pooling raw data from eight double-blind placebo-controlled experimental studies conducted between 1999 and 2008. The analysis included 110 healthy subjects who had received 1-4 oral doses of psilocybin (45-315 µg/kg body weight). Although psilocybin dose-dependently induced profound changes in mood, perception, thought and self-experience, most subjects described the experience as pleasurable, enriching and non-threatening. Acute adverse drug reactions, characterized by strong dysphoria and/or anxiety/panic, occurred only in the two highest dose conditions in a relatively small proportion of subjects. All acute adverse drug reactions were successfully managed by providing interpersonal support and did not need psychopharmacological intervention. Follow-up questionnaires indicated no subsequent drug abuse, persisting perception disorders, prolonged psychosis or other long-term impairment of functioning in any of our subjects. The results suggest that the administration of moderate doses of psilocybin to healthy, high-functioning and well-prepared subjects in the context of a carefully monitored research environment is associated with an acceptable level of risk.

http://journals.sagepub.com/doi/pdf/10.1177/0269881110382466

Acute, subacute and long-term subjective effects of psilocybin in healthy humans: a pooled analysis of experimental studies.

Psilocybin (4-phosphoryloxy-N,N-dimethyltryptamine) is the major psychoactive alkaloid of some species of mushrooms distributed worldwide. These mushrooms represent a growing problem regarding hallucinogenic drug abuse. Despite its experimental medical use in the 1960s, only very few pharmacological data about psilocybin were known until recently. Because of its still growing capacity for abuse and the widely dispersed data this review presents all the available pharmacological data about psilocybin.

/pdf/the-pharmacology-of-psilocybin-28gzi2cfsg.pdf

The pharmacology of psilocybin

Psychiatry & the psychedelic drugs. Past, present & future.

http://whereareyouquetzalcoatl.com/Xochipilli_TylsEtAll2014.pdf

Psilocybin – Summary of knowledge and new perspectives

The psychotropically active principles of the Mexican hallucinogenic fungus Psilocybe maxicana HEIM have been isolated and obtained in crystalline form. The two new substances, which have been called psilocybin and psilocin, are present in the fruit bodies, the artificially cultivated mycelium and in the sclerotia. The dried mushroom contains 0.2 to 0.4 per cent psilocybin. Psilocin is present, at the most, in trace amounts only.

Psilocybin und Psilocin, zwei psychotrope Wirkstoffe aus mexikanischen Rauschpilzen

Es wird eine rationelle Synthese fur das Bufotenin und andere ω-N-substituierte 5-Oxy-tryptamine angegeben. Folgende neue Verbindungen aus der Reihe der Oxy-tryptamine werden beschrieben: 5-Oxy-ω-N-methyl-tryptamin, 5-Oxy-ω-N-athyl-tryptamin, 5-Oxy-ω-N, N-diathyl-tryptamin, 5-Oxy-ω-N-β-aminoathyl-tryptamin, N-[β-(5-Oxy-indolyl-(3))-athyl]-piperidin, sowie zwei Stellungsisomere des Serotonins, das 4-Oxy-tryptamin und das 6-Oxy-tryptamin.

Eine neue Synthese von Bufotenin und verwandten Oxy‐tryptaminen. 40. Mitteilung über Mutterkornalkaloide

Die Aufhebung des Asymmetriezentrums am Kohlenstoffatom 8 durch β-Aminocarbonsaure-Spaltung ergibt ein identisches Lactam aus Lysergsaure und Isolysergsaure, was zur Formulierung dieser Isomeren als Diastereomere fuhrt. Ihre hydrierbare Doppelbindung wird auf Grund des Vergleichs der Absorptionsspektren in Δ9-10 festgelegt. Der Hofmann'sche Abbau, die Decarboxylierung und die Hydrierung von Lysergsaure und Isolysergsaure werden in Ubereinstimmung mit dieser Auffassung formuliert. Fur den Mechanismus der reversiblen Lysergsaure-Isolysergsaure-Umlagerung wird eine Erklarung gegeben.

Über die Isomerie von Lysergsäure und Isolysergsäure. 14. Mitteilung über Mutterkornalkaloide

The preparation and BECKMANN rearrangement of 4-tosyloxyimino-4,5,6,7-tetrahydroindoles are described. The structures of the stereoisomeric parent oximes, their tosylates, and of the products of their BECKMANN rearrangement have been confirmed by NMR and IR spectroscopy.

Herstellung und Eigenschaften von Oximen des 4-Oxo-4,5,6,7-tetrahydroindols und ihre Umlagerung in Pyrrolo-azepine 6. Mitteilung über synthetische Indol-Verbindungen [1]†

A stereoselective reduction of d-lysergic acid amides to the 2,3-dihydro derivatives is described. These new dihydro-compounds can be dehydrogenated and oxidised with potassium nitroso-disulphonate to form the corresponding 12-hydrosy-d-lysergic acid amides besides the corresponding d-lysergic acid amides.

Selektive Reduktions- und Oxydationsreaktionen an lysergsäure- Derivaten. 2.3-Dihydro- und 12-Hydroxy-lysergsäureamide. 59. Mitteilung über Mutterkornalkaloide†

F. Troxler

Papers

Psilocybin und Psilocin, zwei psychotrope Wirkstoffe aus mexikanischen Rauschpilzen

Eine neue Synthese von Bufotenin und verwandten Oxy‐tryptaminen. 40. Mitteilung über Mutterkornalkaloide

Über die Isomerie von Lysergsäure und Isolysergsäure. 14. Mitteilung über Mutterkornalkaloide

Herstellung und Eigenschaften von Oximen des 4-Oxo-4,5,6,7-tetrahydroindols und ihre Umlagerung in Pyrrolo-azepine 6. Mitteilung über synthetische Indol-Verbindungen [1]†

Selektive Reduktions- und Oxydationsreaktionen an lysergsäure- Derivaten. 2.3-Dihydro- und 12-Hydroxy-lysergsäureamide. 59. Mitteilung über Mutterkornalkaloide†