Accurate and sensitive analytical methods for psilocin (PC) and psilocybin (PB), tryptamine-type hallucinogens contained in "magic mushrooms," were investigated using liquid chromatography-mass spectrometry (LC-MS) and liquid chromatography-tandem mass spectrometry (LC-MS-MS). The chromatographic separation on an ODS column and mass spectral information gave...
Accurate and sensitive analytical methods for psilocin (PC) and psilocybin (PB), tryptamine-type hallucinogens contained in "magic mushrooms," were investigated using liquid chromatography-mass spectrometry (LC-MS) and liquid chromatography-tandem mass spectrometry (LC-MS-MS). The chromatographic separation on an ODS column and mass spectral information gave...
A25-year-old man was brought to the emergency department from a late-night dance club. A friend reported that the patient commonly used designer drugs that he purchased over the Internet. While at the club, he started to vomit and experience visual hallucinations. He had no previous medical history and took no prescription medications. On searching the patie...
IntroductionA wide range of fungi and medicinal herbs, rich in hallucinogenic substances and widely used for mystic and medicinal purposes, can give rise to neurotoxic symptoms.DevelopmentWe review the toxic syndromes that can arise from the ingestion of hallucinogenic fungi, cacti and plants, together with descriptions of cases of acute poisoning resulting ...
In the context of excessive use of natural or synthetic psychoactive substances, with stimulating, psychedelic and hallucinogenic effects, an increase, if not a recurrence, in consumption of Psilocybe semilanceata has been observed in France over some fifteen years. Psilocybin and psilocin are the active compounds, responsible for the hallucinogenic effects ...
The enantiomers of 3-(N-methylpyrrolidin-2-ylmethyl)-5-methoxyindole, 1, and 3-(N-methylpyrrolidin-2-ylmethyl)-4-hydoxyindole, 3, were prepared using an asymmetric synthesis that employed (+)- or (-)-proline. A new approach was developed that had certain advantages over the synthesis originally reported for the isomers of 1. (+/-)-3-(N-Methylpyrrolidin-3-yl)...
An important determinant of the neurobehavioral responses induced by a drug is its relative receptor selectivity. The molecular basis of ligand selectivity of hallucinogenic and nonhallucinogenic compounds of varying structural classes for the human 5-hydroxytryptamine (5-HT)2A and 5-HT2C receptors was investigated with the use of reciprocal site-directed mu...
Several fungi species collected in the Hawaiian Islands have been reported to be psychoactive. Previous chemical analyses together with the present study indicate that 5 coprophilous and one non-coprophilous species occurring in the islands are now known to contain psychoactive alkaloids. At least some of these species are consumed in the Hawaiian Islands, a...
The occurrence of tryptamine derivatives and urea in Panaeolus cyanescens, also known as Copelandia cyanescens, from Australia, Hawaii and Thailand was investigated. All 70 collections contained psilocin, serotonin and urea. Those from Hawaii were also relatively rich in psilocybin, whereas the species from Australia and Thailand were virtually exempt of thi...
Mycelial cultures of PSILOCYBE CUBENSIS, with the ability to form psilocybin and psilocin DE-NOVO, also hydroxylated and methylated fed tryptamine to give psilocin in up to 3.3% dry mass of the obtained fruit bodies. By using HPLC and TLC, it was found that these mushrooms contain only a small amount of psilocybin (0.01-0.2% dry mass). The values of psilocin...
Analysis of Gymnopilus purpuratus from two localities in the G.D.R. revealed the presence of psilocybin, psilocin and low concentrations of baeocystin. Psilocybin levels varied from 0.07 % up to 0.33 % of dry weight of the bluing basidiocarps. The psilocin content was high and reached 0.31 % of dry weight. The highest concentrations of the alkaloids were fou...
Mycelial cultures of Psilocybe cubensis capable of forming psilocybin and psilocin de novo display a high capacity for hydroxylation of tryptamine derivatives at the 4-position. A specific biotransformation of added synthetic N,N-diethyl-tryptamine was found. Thus high amounts of 4-hydroxy-N,N-diethyltryptamine (up to 3.3%) and a minor quantity of 4-phosphor...
The content of tryptamine derivatives in Psilocybe semilanceata, a popular hallucinogenic mushroom, was measured by high-performance liquid chromatography. Most of the 52 samples have been collected at several localities in Switzerland during a 1-5 year period. The content of psilocybin and baeocystin varied in the range of 0.21-2.02% and 0.05-0.77%, respect...
Seven taxa of agarics reported in literature to contain psilocybin (viz. Psathyrella candolleana, Gymnopilus spectabilis, G. fulgens, Hygrocybe psittacina var. psittacina and var. californica, Rickenella fibula, R. swartzii) have been analysed for psilocybin and related tryptamines with negative results.
Tryptamine produces pharmacologic effects in man and the chronic spinal dog which are similar to those produced by LSD, mescaline, psilocin, DMT, DOM and DOB. These effects include tachycardia, tachypnea, mydriasis, hyperreflexia, behavioral changes and in man, hallucinations. Chronic spinal dogs treated chronically with LSD became tolerant to its ability to...
Abstract14C- and 3H-Labelled psilocin (4-hydroxy-N,N-dimethyl-tryptamine), the principal, active agent of hallucinogenic mushrooms, was synthesized from 2-methyl-3-nitrophenol via 4-benzyloxyindole. 14C-Labelled potassium cyanide was reacted with 4-benzyloxygramine (obtained from 4-benzyloxyindole) to give 14C-4-benzyloxy-3-indole acetic acid, an intermediat...
Using high performance liquid and thin-layer chromatographic methods more than 100 species of fungi from Europe belonging to 18 genera were analysed for the hallucinogenic compound psilocybin and for some related tryptamine derivatives. Psilocybin, psilocin and/or baeocystin were found in 3 PSILOCYBE 1 PANAEOLUS, 5 INOCYBES and one PLUTEUS. PSILOCYBE SEMILAN...
The presence of psilocybin and its monomethyl analogue baeocystin is for the first time demonstrated in five taxa of the genus Inocybe, viz. I. coelestium, I. corydalina var. corydalina, I. corydalina var. erinaceomorpha, I. haemacta and I. aeruginascens. These taxa are characterized by a glaucous coloration of the stipe. A sixth taxon, I. calamistrata, whic...
