Psilocin (1) is the dephosphorylated and psychotropic metabolite of the mushroom natural product psilocybin. Oxidation of the phenolic hydroxy group at the C-4 position of 1 results in formation of oligomeric indoloquinoid chromophores responsible for the iconic blueing of bruised psilocybin-producing mushrooms. Based on previous NMR experiments, the hypothe...
The solid-state structures of the salts of three psilacetin derivatives, namely, 4-acet-oxy-N-eth-yl-N-methyl-tryptammonium (4-AcO-MET) hydro-fumarate {sys-tematic name: [2-(4-acet-yloxy-1H-indol-3-yl)eth-yl](meth-yl)ethyl-aza-nium 3-carb-oxy-prop-2-enoate}, C15H21N2O2 +·C4H3O4 -, 4-acet-oxy-N-allyl-N-methyl-tryptammonium (4-AcO-MALT) hydro-fumarate {systema...
The 5-HT2A receptor is thought to be the primary target for psilocybin (4-phosphoryloxy-N,N-dimethyltryptamine) and other serotonergic hallucinogens (psychedelic drugs). Although a large amount of experimental work has been conducted to characterize the pharmacology of psilocybin and its dephosphorylated metabolite psilocin (4-hydroxy-N,N-dimethyltryptamine)...
Psilocybin is a tryptamine-derived psychoactive alkaloid found mainly in the fungal genus Psilocybe, among others, and is the active ingredient in so-called "magic mushrooms". Although its notoriety originates from its psychotropic properties and popular use as a recreational drug, clinical trials have recently recognized psilocybin as a promising candidate ...
The solid-state structures of the salts of two substituted tryptamines, namely N -isopropyl- N -methyltryptaminium (MiPT) fumarate {systematic name: [2-(1 H -indol-3-yl)ethyl](methyl)propan-2-ylazanium 3-carboxyprop-2-enoate}, C14 H21 N2 + ·C4 H3 O4 −, and 4-hydroxy- N -isopropyl- N -methyltryptaminium (4-HO-MiPT) fumarate monohydrate {systematic name: [2-(4...
AbstractThe selective indole alkylation reaction applying the Ir-catalyzed-borrowing hydrogen methodology and using amino alcohols (II), (V), (VII) as suitable nitrogen-containing electrophiles is reported.
Substances of plant origin have been used to induce hallucinations for a long time, in religious ceremonies and rituals as well as in pain relief. Psilocybin and psilocin naturally occur in the fungal genus Psilocybe. Due to the psychedelic effects and relative harmlessness of these substances and the fact that they do not cause physical addiction, psilocybi...
Sixty years ago, the ethnomycologist R. G. Wasson discovered an ancient mushroom cult in Oaxaca, Mexico.1, 2 The famous mycologist R. Heim classified the psychoactive mushroom species in the genera Psilocybe and the eminent natural product chemist Albert Hofmann published the isolation, structural elucidation and synthesis of the new alkaloids psilocybin and...
ObjectivesUntil recently, routine toxicological analysis of some hallucinogens in biological material posed problems which were only resolved after the introduction of modern analytic systems into toxicological laboratories. The most frequent hallucinogens in clinical and forensic toxicology can be grouped as: cannabinoids, tropane alkaloids, N,N-dimethyltry...
An SAR study of psilocybin and psilocin derivatives reveals that 1-methylpsilocin is a selective agonist at the h5-HT(2C) receptor. The corresponding phosphate derivative, 1-methylpsilocybin, shows efficacy in an animal model for obsessive-compulsive disorder, as does 4-fluoro-N,N-dimethyltryptamine. These results suggest a new area for development of novel ...
Since June 6, 2002, psilocin and psilocybin-containing fungi (commonly called "magic mushrooms") have been regulated by the Narcotics and Psychotropics Control Law in Japan. However, various fly agaric-related products are now entering the Japanese market via the internet. In this study, fly agaric-related products available in this way were investigated for...
Derivatives of psilocin with omega-functionalized alkyl spacers in position 1 of the indole ring were synthesized as haptens for use in a radioimmunoassay. Whereas the psilocin analogues with a 3-aminopropyl and a 4-aminobutyl moiety at the indole nitrogen decomposed during synthesis, the analogous 3-carboxypropyl psilocin derivative proved to be stable. Thi...
Psilocin analogs having either a formyl group (9-12) or a bromine atom (13-18) at the 5- or 7-position have been prepared for the first time. Syntheses of 5- and 7-bromo derivatives of 4-hydroxy- (23, 24, 28) and 4-benzyloxyindole-3-carbaldehyde (19, 25, 29, 30), 4-benzyloxyindole-3-acetonitriles (20, 31), and 4-benzyloxy-N,N-dimethyltryptamine (32, 34, 35) ...
The applications of LC-API-MS in routine forensic toxicological casework were presented. This technique has been used for routine determination of several groups of drugs: opiate agonists (like morphine, codeine, dihydrocodeine and their glucuronides, methadone, buprenorphine) cocaine and its metabolites (benzoylecgonine and ecgonine methyl ester), amphetami...
A review of techniques used to screen biological specimens for the presence of drugs was conducted with particular reference to systematic toxicological analysis. Extraction systems of both the liquid-liquid and solid-phase type show little apparent difference in their relative ability to extract a range of drugs according to their physio-chemical properties...
Bufotenine, an isomer of psilocin, is a controlled Schedule I hallucinogenic substance under the New York state and Federal laws. Bufotenine was identified in 42 case samples received at the New York City Police Laboratory since May 1992. The samples were hard, resinous, dark reddish-brown material, sold on the streets as "hashish". A few other cases were al...
The occurrence and extraction of indole derivatives in six species from four genera of higher fungi were investigated. By using pure methanol for extraction of the mushrooms analysis revealed the highest concentrations of psilocybin and baeocystin. The psilocin content of the species was higher by using aqueous solutions of alcohols than with methanol alone ...
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 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...
