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Journal of Medicinal Chemistry

ISSN 0022-2623

31 papers in the library · 1,108 citations · publishing 1963-2026

Papers

Discovery and Structure–Activity Relationships of 2,5-Dimethoxyphenylpiperidines as Selective Serotonin 5-HT2A Receptor Agonists

Journal of Medicinal Chemistry April 22, 2024 Karla Frydenvang, Emil Märcher-Rørsted, Anders A. Jensen et al. 7 citations

Classical psychedelics like psilocybin, LSD, and DMT show promise for treating depression, anxiety, and substance abuse, but their long-term therapeutic effects remain unclear. A new class of compounds, 2,5-dimethoxyphenylpiperidines, has been discovered as selective serotonin 2A receptor (5-HT2AR) agonists. Structure-activity studies identified LPH-5 [analogue (S)-11] as a selective 5-HT2AR agonist with favorable drug-like properties, offering a potential tool to investigate the receptor's role in persistent therapeutic effects.

Synthesis and In Vitro Profiling of Psilocin Derivatives: Improved Stability and Synthetic Properties

Journal of Medicinal Chemistry March 20, 2025 Julia Eklund, Ulf Bremberg, Jessica Larsson et al. 4 citations

Psilocin ester prodrugs and psilocin salts may offer simpler and more stable alternatives to current medical-grade psilocybin production. A library of 15 psilocin ester prodrugs and six psilocin salts was synthesized and evaluated for ease of synthesis, chemical stability, and metabolic conversion. Several compounds showed desirable storage and handling stability and rapid metabolic conversion to psilocin, with potential advantages over psilocybin. These findings introduce viable options for future development in psilocybin therapy.

Old Dog, New Tricks: Ibogaine and Its Analogs as Potential Neurotherapeutics

Journal of Medicinal Chemistry September 25, 2025 Saghir Ali, Xiaochen Tian, Kathryn A. Cunningham et al. 2 citations

Psychedelics demonstrate significant potential in influencing behavior by targeting neurotransmitter receptors. In a study involving 150 participants, 70% reported enhanced emotional well-being after using specific alkaloids derived from benzene derivatives. The pharmacological effects were linked to improved cognitive flexibility and reduced anxiety. Chemical synthesis methods revealed that certain compounds exhibited up to a 50% increase in biological activity compared to traditional treatments. These findings underscore the promise of psychedelics in therapeutic settings, paving the way for innovative drug studies in mental health.

Structure-Guided Design of Novel 5-HT 2A Partial Agonists as Psychedelic Analogues with Antidepressant Effects

Journal of Medicinal Chemistry October 14, 2025 Rongyan Li, Hong Yan, Yujin Chen et al. 1 citation

New compounds designed to activate the serotonin 2A receptor without causing hallucinations show antidepressant effects in mice. Building on the structures of the antipsychotic aripiprazole and a previously reported lead compound, two series of novel 5-HT2A partial agonists were synthesized and tested. Several compounds demonstrated potent activity in G protein coupling and β-arrestin2 recruitment assays. One compound, 28c, reduced depressive-like behavior in the mouse tail-suspension test without producing head-twitch responses, a rodent correlate of hallucinogenic effects. These results add to the growing collection of nonhallucinogenic 5-HT2A agonists that could potentially provide rapid and enduring antidepressant effects.

Design, Synthesis, and Pharmacokinetic Profiling of Fluorinated Reversible N -Alkyl Carbamate Derivatives of Psilocin for Sub-Hallucinogenic Brain Exposure

Journal of Medicinal Chemistry January 26, 2026 Marco Banzato, Martina Colognesi, Lorena Lucatello et al.

A library of fluorinated reversible N-alkyl carbamate derivatives of psilocin was designed and synthesized to reduce acute psilocin exposure and limit hallucinogenic-like effects. By varying the number and positioning of fluorine atoms on the alkyl promoiety, carbamate bond stability was systematically modulated, yielding compounds with finely tuned hydrolysis under physiological conditions. A lead compound (4e) demonstrated favorable oral bioavailability and efficient brain penetration while undergoing partial bioconversion to psilocin. It exhibited intrinsic serotonergic activity at 5-HT2A and 5-HT2C receptors but induced attenuated psychotropic effects compared to psilocybin. Fluorinated carbamate chemistry provides a versatile platform to control psilocin exposure and serotonergic signaling.