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ChemRxiv

ISSN 2573-2293

11 papers in the library · 6 citations · publishing 2018-2026

Papers

Rapid quantification of Psilocybin with reversed-phase HPLC and single-wavelength detection

ChemRxiv October 26, 2021 Alexzander Samuelsson, Eric Janusson, Sajni Shah et al. 2 citations

Psilocybin and psilocin, the main psychoactive alkaloids in Psilocybe mushrooms, are gaining renewed attention for therapeutic use, yet validated, rapid methods for analyzing their purity are scarce. To address this, the authors developed an inexpensive high-performance liquid chromatography (HPLC) technique using readily available equipment and dilute reagents. Aqueous ammonium formate (0.143 mM) effectively controlled psilocybin Zwitterion resolution, and a standard C18 column achieved excellent separation between the two compounds. The method runs in under two minutes, meeting high-throughput needs. Validation with certified standards showed it to be accurate (3.5% bias for psilocybin), reliable (0.32% relative standard deviation), and efficient (capacity factor k’ = 1.78).

Fungi Fiction: Analytical Investigation into the Church Of Psilomethoxin's Alleged Novel Compound Using UPLC-HRMS

ChemRxiv June 2, 2023 Samuel E. Williamson, Alexander M. Sherwood 1 citation

The Church of Psilomethoxin claims its sacrament is a novel tryptamine, psilomethoxin, produced by adding 5-MeO-DMT to the substrate of cultivated Psilocybe mushrooms. Using ultra-performance liquid chromatography with high-resolution mass spectrometry (UPLC-HRMS) and authentic reference standards, this analysis found no evidence of psilomethoxin in samples of the material sold to members online. Instead, the samples unambiguously contained psilocybin, baeocystin, and psilocin. The findings indicate that the church's claims about biosynthesis of psilomethoxin are likely misguided, with implications for public health and safety.

Characterization of the Binding Poses of Classical and Photoswitchable Psychedelics Interacting with 5-HT2AR

ChemRxiv February 7, 2023 Vito F. Palmisano, Claudio Agnorelli, David Erritzøe et al. 1 citation

Classic psychedelics target the 5-HT2A serotonin receptor, but their precise mode of action remains unclear. Computational modeling of the receptor's orthosteric binding pocket for several psychedelics—including serotonin, LSD, DMT, and a photoswitchable analog (AzoDMT)—revealed two nearly equivalent binding poses. LSD and serotonin preferred the canonical crystallized pose, whereas DMT and 4-OH-DMT slightly favored a newly identified pose. The cis form of AzoDMT was the most stable, and its azobenzene domain interacted with the same residue (L229) responsible for LSD's extracellular loop closure. These simulations clarify drug–protein interactions and may aid development of new psychedelic compounds.

A Single Administration of the Atypical Psychedelic Ibogaine or its Metabolite Noribogaine Induces an Antidepressant-like Effect in Rats

ChemRxiv March 19, 2020 Paola Rodrı́guez, Jessika Urbanavicius, José Pedro Prieto et al. 1 citation

Ibogaine and its main metabolite noribogaine produce antidepressant-like effects in rats in a dose- and time-dependent manner, without altering locomotor activity. Noribogaine's effect is short-lived (30 minutes) and correlates with high brain concentrations (estimated > 8 µM free drug), while ibogaine's effect is significant at 3 hours. At that time, both compounds are present in the brain at concentrations (ibogaine ~0.5 µM, noribogaine ~2.4 µM) that alone cannot produce the same behavioral outcome, suggesting a polypharmacological mechanism underlies their antidepressant-like effects.

Effect of Liner Properties on the Analysis of Lysergic Acid Diethylamide (LSD) Analogs

ChemRxiv Sarah Shuda 1 citation

LSD and related psychedelic drugs are often present at low concentrations on forensic evidence, requiring sensitive detection. The liner inside the injection port of a gas chromatograph (GC) affects how well these compounds are vaporized and transferred to the column. Testing twelve different liners—varying in shape, packing material, and chemical deactivation—showed that liners containing packing material (like glass wool) produced significantly higher peak areas than unpacked liners. Liner geometry had a smaller effect, only mattering with one deactivation type when glass wool was absent. Base deactivation improved peak area compared to standard and Topaz deactivation in straight liners with packing. Over seventy sample runs, base-deactivated and standard liners maintained consistent response, while Topaz-deactivated liners lost 52–68% response after the first injection and 30–54% from first to last injection.

Semi-Quantitative Estimation of MDMA Tablet Dosage and Cocaine/Ketamine Purity Using a Simple to Operate Field-Portable Device

ChemRxiv June 9, 2026 Matthew Gardner, Alexander Power, Anca Frinculescu et al.

A low-cost, field-portable device using Hybridized Spectral Fingerprinting (HSF) and deep learning can rapidly screen illicit drug samples for MDMA dosage and cocaine/ketamine purity. A convolutional neural network trained on 62 GC-EI-MS quantified MDMA tablets classified samples into 1–170 mg or 170–300 mg dosage brackets, achieving 98% accuracy on 195 external test samples. Another model trained on 1H NMR quantified cocaine and ketamine samples provided presumptive identification and semi-quantitative purity estimation with 96% accuracy on 47 external samples. The approach supports harm reduction and police screening by alerting on potentially harmful MDMA tablets and estimating cocaine and ketamine purity.

A streamlined synthesis of 5-methoxy-N,N-dimethyltryptamine, bufotenin, and bufotenin prodrugs from melatonin

ChemRxiv November 26, 2025 Anton A. Homon, P. V. Vara Prasad, Elham Pourian et al.

A streamlined, chromatography-free synthesis of 5-MeO-DMT from melatonin achieves 76% overall yield, producing 64 g of analytically pure product in under 5 days. Demethylation of 5-MeO-DMT yields bufotenin hydrobromide in 51% yield (22 g) within an additional 2 days. Candidate prodrugs of bufotenin are prepared to potentially improve nanoformulation and blood-brain-barrier passive uptake. The method uses inexpensive, widely available melatonin, avoiding expensive starting materials, extensive chromatography, and late-stage chemistries that raise toxicity concerns.

We licked the frogs so you don’t have to: A comprehensive history and analysis of the chemical syntheses of the classical psychedelics Bufotenin(e) and 5-methoxy-N,N-dimethyltryptamine

ChemRxiv June 26, 2025 Anton A. Homon, Jaxon Laramie, John J. Hayward et al.

Bufotenin and 5-MeO-DMT are potent psychedelics found in plants and toad secretions, but their therapeutic potential for psychological disorders and inflammatory or neurodegenerative diseases has been hindered by prohibition and limited commercial availability. This review collates all known academic and patent syntheses of bufotenin from 1935 to 2024, comparing routes to help researchers choose the most suitable method. The authors highlight challenges that need solving to reduce costs for future commercial-scale production, aiming to support the growing clinical and preclinical research into these compounds.

Hemp proteins conjugated with green tea polyphenol extract form de novo plant-sourced emulsifiers suitable for nanodelivery systems bearing lipophilic psychopharmaceuticals

ChemRxiv February 27, 2025 William Charles Hosie, Mary Augustina Egbuta, Kasra Razmkhah et al.

A new class of biocompatible emulsifiers was created by conjugating hemp protein with green tea polyphenols using a simple pH-assisted coupling protocol. These emulsifiers were used to produce hemp oil nanoemulsions enriched with 5-methoxy-N,N-dimethyltryptamine (5-MeO-DMT), achieving average droplet sizes of about 200 nm and ζ potential values of about -40 mV. The polyphenol-conjugated emulsifiers protected the sensitive drug under simulated oxidative stress, indicating retained antioxidant properties. The emulsions resisted various stressors and showed colloidal stability for 4 weeks without phase separation. Cellular uptake was confirmed by imaging, and in vitro cytotoxicity assays showed acceptable cell viability with drug-loaded nanoemulsions, offering an ingestible formulation for improved bioavailability of 5-MeO-DMT.

Ibogaine Modifies GDNF, BDNF and NGF Expression in Brain Regions Involved in Mesocorticolimbic and Nigral Dopaminergic Circuits

ChemRxiv October 29, 2018 Soledad Marton, Bruno González, Sebastián Rodríguez et al.

Ibogaine, a psychedelic alkaloid, alters the expression of three neurotrophic factors—GDNF, BDNF, and NGF—in rat brain regions containing dopamine neurons. A single injection of 20 or 40 mg/kg ibogaine increased expression of these factors after 24 hours in a dose- and region-specific manner. The higher dose selectively raised GDNF in the ventral tegmental area and substantia nigra. Both doses increased BDNF in the nucleus accumbens, substantia nigra, and prefrontal cortex, while the higher dose also raised BDNF in the ventral tegmental area. NGF increased in all regions after the higher dose. Mature GDNF protein rose in the ventral tegmental area, and proBDNF increased in the nucleus accumbens. These changes may contribute to ibogaine's anti-addictive properties.

Membrane Permeation of Psychedelic Compounds

ChemRxiv Vito Federico Palmisano, Claudio Agnorelli, Andrea Fagiolini et al.

The ability of classic psychedelics to permeate neuronal membranes and reach intracellular 5-HT2A receptors is critical for their therapeutic effects. Using molecular dynamics simulations, this computational study examined how structural modifications to tryptamines affect membrane permeability. Dimethylation of the primary amine group and adding a methoxy group at position 5 increased permeability. In contrast, substitutions at other positions on the indole ring and protonation of the molecules raised the energy barrier at the bilayer center, making the compounds highly impermeable. These findings can guide future drug design to develop psychedelics with enhanced activity.