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...
Fifteen rats were trained to discriminate between the tryptamine hallucinogen psilocybin (4-phosphoryloxy-N,N-dimethyltryptamine; 1.0 mg/kg) and saline in a two-lever choice task. Dose-response and time-response curves were obtained. The psilocybin cue generalized to psilocin (the dephosphorylated congener of psilocybin) and to the prototypical indoleamine h...
The specific binding of 3H-serotonin to calf caudate homogenate was studied. The dissociation constant was 2nM and the number of specific sites was 14fmoles/mg protein. Of many drugs tested, inhibition of specific 3H-serotonin binding occurred almost exclusively with serotonin agonists and antagonists. The concentrations for 50% inhibition of 3H-serotonin bi...
The effects of several indoleamines and phenethylamines were studied in the chronic spinal dog and compared with two standard drugs, LSD and amphetamine. In the nontolerant chronic spinal dog, their effects on a variety of physiologic and behavioral functions were measured in untreated dogs, as well as dogs treated with certain antagonists. The effects of th...
The dopaminergic actions of various hallucinogenic drugs were assessed by examining their effects on turning behavior in rats with unilateral 6-hydroxydopamine lesions of the nigro-striatal pathway. LSD (0.1 and 0.2 mg/kg) produced strong contralateral turning, indicating that it is a potent dopamine receptor agonist, while BOL (5 mg/kg), a non-hallucinogeni...
D-lysergic acid diethylamide (LSD) displays (1) the phenylethylamine pattern present in mescaline, cyclazocine and catecholamines and (2) the 4-substituted tryptamine structure of psilocybin which is a serotonin analog. Hence (a) Naloxone--a blocker of the LSD-like side effects of cyclazocine--should (and does) block effects of LSD, and (b) cross-tolerance m...
