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.

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The pharmacology of psilocybin

Selected Contents from Volume I: Indole Alkaloids Diketopiperazines Chaetoglobosins/Cytochalasins Aflavinines Tryptoquivalines Penitrems/Lolitrems Selected Contents from Volume II: Antheridiols and Oogoniols Ganoderic Acids Ganoderiols Lucidenic Acids Azasteroids Fusidanes and Protostanes Selected Contents from Volume III: Cercophorins Fiscalins Palmarumycins Phomosines Radicinins Modified Trichothecenes

Handbook of secondary fungal metabolites

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

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

By selection of certain strains of the ergot fungus found on Pennisetum typhoideum Rich. (a tropical millet) and modifying the substrate we succeeded in increasing the alkaloid yield in saprophytic cultures up to 1000–1500 mg alkaloids per liter of culture filtrate and increasing the alkaloid content of the mycelium to 1% of its dry weight.

Neue Alkaloide aus der saprophytischen Kultur des Mutterkornpilzes von Pennisetum typhoideum Rich. 42. Mitteilung über Mutterkornalkaloide

Aus den Sklerotien eines auf der afrikanischen Kolbenhirse Pennisetum typhoideum Rich. gefundenen Mutterkornpilzes konnte das Alkaloid Agroclavin isoliert und identifiziert werden. Aus den Sklerotien wurden Pilzstamme isoliert, welche die Fahigkeit besitzen, in saprophytischer Kultur in vitro Alkaloide zu bilden. Aus Kulturfiltraten und aus Mycelien konnten die beiden bereits bekannten Alkaloide Agroclavin und Elymoclavin, sowie ein neues Alkaloid mit der Bruttoformel C16H18O2N2, fur das wir die Bezeichnung Penniclavin vorschlagen, isoliert und charakterisiert werden.

Die Alkaloide eines Mutterkornpilzes von Pennisetum typhoideum Rich. und deren Bildung in saprophytischer Kultur. 36. Mitteilung über Mutterkornalkaloide

Three monoconidial strains ofClaviceps purpurea were grown parasitically on rye and saprophytically on a nutrient medium. The qualitative alkaloid spectra were nearly identical in the sclerotia and in the corresponding saprophytic cultures, while the quantitative distribution of some of the alkaloids differed considerably.

Vergleich der Alkaloidbildung vonClaviceps purpurea in parasitischer und saprophytischer Kultur

Durch Zusatz von Elymoclavin und von Agroclavin zu Kulturen des mexikanischen Rauschpilzes Psilocybe semperviva HEIMet CAILLEUX konnten diese beiden Mutterkornalkaloide am C-8 hydroxyliert werden, wobei aus Elymoclavin Pennicalvin und Isopenniclavin, aus Agroclavin Setoclavin und Spuren Isosetoclavin entstanden.

Mikrobiologische Hydroxylierungen an Mutterkornalkaloiden vom Clavin‐Typus mit dem mexikanischen Rauschpilz Psilocybe semperviva HEIMet CAILLEUX. 52. Mitteilung über Mutterkornalkaloide

A. Brack

Papers

Psilocybin und Psilocin, zwei psychotrope Wirkstoffe aus mexikanischen Rauschpilzen

Neue Alkaloide aus der saprophytischen Kultur des Mutterkornpilzes von Pennisetum typhoideum Rich. 42. Mitteilung über Mutterkornalkaloide

Die Alkaloide eines Mutterkornpilzes von Pennisetum typhoideum Rich. und deren Bildung in saprophytischer Kultur. 36. Mitteilung über Mutterkornalkaloide

Vergleich der Alkaloidbildung vonClaviceps purpurea in parasitischer und saprophytischer Kultur

Mikrobiologische Hydroxylierungen an Mutterkornalkaloiden vom Clavin‐Typus mit dem mexikanischen Rauschpilz Psilocybe semperviva HEIMet CAILLEUX. 52. Mitteilung über Mutterkornalkaloide