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Australian Journal of Chemistry

ISSN 0004-9425

6 papers in the library · 37 citations · publishing 1970-2024

Papers

The occurrence of the psychotomimetic agent psilocybin in an Australian agaric, Psilocybe subaeruginosa

Australian Journal of Chemistry April 1, 1970 J. Picker, R. W. Rickards 18 citations

Psilocybin and its dephosphorylated derivative psilocin were first isolated from the hallucinogenic Mexican mushroom Psilocybe mexicana Heim. These compounds have since been found in many species of the genus Psilocybe from Mexico, North America, and Europe, as well as in Stropharia cubensis from Mexico, Thailand, and Cambodia, Conocybe cyanopus and amithiill from North America, a Copelandia from France, and Panaeolus sphinctrinus from Mexico (though this last occurrence is unconfirmed). Mono- and bis-demethyl analogues occur together with psilocybin in submerged cultures of Ps. baeocystis. However, not all Psilocybe species contain these metabolites; Ps. yungensis and atrobrunnea lack them.

Alkaloids from the entheogenic plant Peganum harmala

Australian Journal of Chemistry July 17, 2023 Daniel G. Anstis, Jessica Liyu, Emma K. Davison et al. 8 citations

The plant Peganum harmala, used in traditional medicine, produces central nervous system symptoms including hallucinations. Its 160 known alkaloids are promising candidates for new entheogenic compounds that could treat mood disorders unresponsive to conventional therapies. However, bioactivity data is scarce, limited to inhibition of monoamine oxidases and cholinesterases in a few cases, with most alkaloids having no reported bioactivity. None of the classic entheogens have been detected in P. harmala, making this alkaloid collection a useful reference for discovering structurally unique entheogens.

Introduction to the chemistry and pharmacology of psychedelic drugs

Australian Journal of Chemistry July 4, 2023 Scott R. Walker, Glenn A. Pullella, Matthew Piggott et al. 5 citations

Psychedelic science is a multi-disciplinary field that has recently gained public attention due to high-profile studies on psychedelic-assisted therapy for difficult-to-treat mental health conditions. This Primer Review provides an overview of the chemistry and pharmacology of psychedelics, covering natural, semi-synthetic, and fully synthetic substances. It begins with a summary of important psychedelic classes and their traditional human use dating back to prehistoric times. The review examines ergolines (e.g., LSD), tryptamines (e.g., psilocybin, DMT), phenethylamines (e.g., mescaline, MDMA), arylcyclohexylamines (e.g., ketamine, PCP), and other naturally occurring drugs like muscimol and salvinorin A. Contributions from pioneers Albert Hofmann and Alexander Shulgin are briefly summarized, with references to primary literature.

A review of psilocybin: chemistry, clinical uses and future research directions

Australian Journal of Chemistry May 16, 2023 Eliza Milliken, Peter Galettis, Jenny Martin 4 citations

Classic psychedelics like psilocybin, ketamine, and LSD activate 5HT2A serotonin receptors and produce individualized subjective effects. Public interest in psychedelic medicine is high, but clinical evidence remains limited. Psilocybin and psilocin are tryptophan-based alkaloids found in several mushroom genera. This review covers the current evidence for psilocybin as a clinical medicine, its chemistry, proposed therapeutic mechanism, and future research directions for psilocybin-based therapies.

Synthesis of R- and S-MDMA via nucleophilic ring-opening of homochiral N-tosylaziridines

Australian Journal of Chemistry July 11, 2023 Katie D. Lewis, Glenn A. Pullella, Han Chern Loh et al. 2 citations

Homochiral (R)- and (S)-MDMA were synthesized in six steps from d- and l-alanine. A copper-catalyzed regioselective ring-opening of an N-tosylaziridine with an aryl Grignard reagent gave high yields and complete regioselectivity. The synthesis preserved configurational integrity, yielding R- and S-MDMA hydrochlorides with enantiopurities greater than 99.5%, confirmed by enantioselective HPLC with fluorescence detection. Applying the same method to make homochiral enantiomers of the α-phenyl analogue UWA-001 failed due to a switch in regioselectivity in the key step.