Alexander M. Sherwood
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View article: In Vitro Psilocybin Synthesis by Co‐Immobilized Enzymes
In Vitro Psilocybin Synthesis by Co‐Immobilized Enzymes Open
Advanced clinical trials investigate the Psilocybe magic mushroom natural product psilocybin as a treatment against major depressive disorder. Currently, synthetic material is used to meet the demand for legitimate pharmaceutical purposes.…
View article: Classification of psychedelics and psychoactive drugs based on brain-wide imaging of cellular c-Fos expression
Classification of psychedelics and psychoactive drugs based on brain-wide imaging of cellular c-Fos expression Open
Psilocybin, ketamine, and MDMA are psychoactive compounds that exert behavioral effects with distinguishable but also overlapping features. The growing interest in using these compounds as therapeutics necessitates preclinical assays that …
View article: Classification of psychedelics and psychoactive drugs based on brain-wide imaging of cellular c-Fos expression
Classification of psychedelics and psychoactive drugs based on brain-wide imaging of cellular c-Fos expression Open
Psilocybin, ketamine, and MDMA are psychoactive compounds that exert behavioral effects with distinguishable but also overlapping features. The growing interest in using these compounds as therapeutics necessitates preclinical assays that …
View article: Psychedelic-like Activity of Norpsilocin Analogues
Psychedelic-like Activity of Norpsilocin Analogues Open
Primary metabolites of mushroom tryptamines, psilocybin and baeocystin (i.e., psilocin and norpsilocin), exhibit potent agonist activity at the serotonin 2A receptor (5-HT2A) in vitro but differ in their 5-HT2A-mediated effects in vivo. In…
View article: Identification of 5-HT<sub>2A</sub>Receptor Signaling Pathways Responsible for Psychedelic Potential
Identification of 5-HT<sub>2A</sub>Receptor Signaling Pathways Responsible for Psychedelic Potential Open
Summary Serotonergic psychedelics possess considerable therapeutic potential. Although 5-HT 2A receptor activation mediates psychedelic effects, prototypical psychedelics activate both 5-HT 2A -Gq/11 and β-arrestin2 signaling, making their…
View article: Swim in the Chiral Pool: MDMA and MDA Enantiomers from Alanine-Derived Precursors
Swim in the Chiral Pool: MDMA and MDA Enantiomers from Alanine-Derived Precursors Open
A divergent two-step process has provided access to optically pure enantiomers of MDMA and MDA, clinically relevant phenylisopropylamine entactogens. Target compounds were synthesized from commercially available alanine-derived aziridines.…
View article: Fungi Fiction: Analytical Investigation into the Church Of Psilomethoxin's Alleged Novel Compound Using UPLC-HRMS
Fungi Fiction: Analytical Investigation into the Church Of Psilomethoxin's Alleged Novel Compound Using UPLC-HRMS Open
The Church of Psilomethoxin claims to produce a novel tryptamine by adding 5-MeO-DMT to the substrate of cultivated Psilocybe mushrooms, which is then biosynthesized into psilomethoxin, the church’s sacrament. In this study, we investigate…
View article: Fungi Fiction: Analytical Investigation into the Church Of Psilomethoxin's Alleged Novel Compound Using UPLC-HRMS
Fungi Fiction: Analytical Investigation into the Church Of Psilomethoxin's Alleged Novel Compound Using UPLC-HRMS Open
The Church of Psilomethoxin claims to produce a novel tryptamine by adding 5-MeO-DMT to the substrate of cultivated Psilocybe mushrooms, which is then biosynthesized into psilomethoxin, the church’s sacrament. In this study, we investigate…
View article: Psychedelics for Medicinal Use: How Will This Alter the Collective Laboratory Consciousness?
Psychedelics for Medicinal Use: How Will This Alter the Collective Laboratory Consciousness? Open
Journal Article Psychedelics for Medicinal Use: How Will This Alter the Collective Laboratory Consciousness? Get access Steven W Cotten, Steven W Cotten Associate Professor, Department of Pathology and Laboratory Medicine, University of No…
View article: 5-MeO-DMT modifies innate behaviors and promotes structural neural plasticity in mice
5-MeO-DMT modifies innate behaviors and promotes structural neural plasticity in mice Open
Serotonergic psychedelics are gaining increasing interest as potential therapeutics for a range of mental illnesses. Compounds with short-lived subjective effects may be clinically useful because dosing time would be reduced, which may imp…
View article: Structure–Activity Relationships for Psilocybin, Baeocystin, Aeruginascin, and Related Analogues to Produce Pharmacological Effects in Mice
Structure–Activity Relationships for Psilocybin, Baeocystin, Aeruginascin, and Related Analogues to Produce Pharmacological Effects in Mice Open
4-Phosphoryloxy-N,N-dimethyltryptamine (psilocybin) is a naturally occurring tertiary amine found in many mushroom species. Psilocybin is a prodrug for 4-hydroxy-N,N-dimethyltryptamine (psilocin), which induces psychedelic effects via agon…
View article: Psilocybin: crystal structure solutions enable phase analysis of prior art and recently patented examples
Psilocybin: crystal structure solutions enable phase analysis of prior art and recently patented examples Open
Psilocybin (systematic name: 3-[2-(dimethylamino)ethyl]-1H-indol-4-yl dihydrogen phosphate) is a zwitterionic tryptamine natural product found in numerous species of fungi known for their psychoactive properties.Following its structural el…
View article: The crystal structure of baeocystin
The crystal structure of baeocystin Open
The title compound, baeocystin or 4-phosphoryloxy- N -methyltryptamine {systematic name: 3-[2-(methylazaniumyl)ethyl]-1 H -indol-4-yl hydrogen phosphate}, C 11 H 15 N 2 O 4 P, has a single zwitterionic molecule in the asymmetric unit. The …
View article: Assessment of Bioactivity‐Modulating Pseudo‐Ring Formation in Psilocin and Related Tryptamines
Assessment of Bioactivity‐Modulating Pseudo‐Ring Formation in Psilocin and Related Tryptamines Open
Psilocybin ( 1 ) is the major alkaloid found in psychedelic mushrooms and acts as a prodrug to psilocin ( 2 , 4‐hydroxy‐ N , N ‐dimethyltryptamine), a potent psychedelic that exerts remarkable alteration of human consciousness. In contrast…
View article: Psilocybin: Characterization of the Metastable Zone Width (MSZW), Control of Anhydrous Polymorphs, and Particle Size Distribution (PSD)
Psilocybin: Characterization of the Metastable Zone Width (MSZW), Control of Anhydrous Polymorphs, and Particle Size Distribution (PSD) Open
Psilocybin, a serotonergic agonist, was granted a "breakthrough therapy" status by the Food and Drug Administration for clinical trials involving major depressive disorder and treatment-resistant depression. The direct phosphorylation of p…
View article: Structure Elucidation and Spectroscopic Analysis of Chromophores Produced by Oxidative Psilocin Dimerization
Structure Elucidation and Spectroscopic Analysis of Chromophores Produced by Oxidative Psilocin Dimerization Open
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 r…
View article: Discriminative-Stimulus Effects of Synthetic Cathinones in Squirrel Monkeys
Discriminative-Stimulus Effects of Synthetic Cathinones in Squirrel Monkeys Open
Background Synthetic cathinones display overlapping behavioral effects with psychostimulants (e.g., methamphetamine [MA]) and/or entactogens (e.g., 3,4-methylenedioxymethaphetamine [MDMA])—presumably reflecting their dopaminergic and/or se…
View article: Chemoenzymatic Synthesis of 5-Methylpsilocybin: A Tryptamine with Potential Psychedelic Activity
Chemoenzymatic Synthesis of 5-Methylpsilocybin: A Tryptamine with Potential Psychedelic Activity Open
A novel analogue of psilocybin was produced by hybrid chemoenzymatic synthesis in sufficient quantity to enable bioassay. Utilizing purified 4-hydroxytryptamine kinase from Psilocybe cubensis, chemically synthesized 5-methylpsilocin (2) wa…
View article: CCDC 1945766: Experimental Crystal Structure Determination
CCDC 1945766: Experimental Crystal Structure Determination Open
An entry from the Cambridge Structural Database, the world’s repository for small molecule crystal structures. The entry contains experimental data from a crystal diffraction study. The deposited dataset for this entry is freely available …
View article: Synthesis and Characterization of 5-MeO-DMT Succinate for Clinical Use
Synthesis and Characterization of 5-MeO-DMT Succinate for Clinical Use Open
To support clinical use, a multigram-scale process has been developed to provide 5-MeO-DMT, a psychedelic natural product found in the parotid gland secretions of the toad, Incilius alvarius. Several synthetic routes were initially explore…
View article: Direct Phosphorylation of Psilocin Enables Optimized cGMP Kilogram-Scale Manufacture of Psilocybin
Direct Phosphorylation of Psilocin Enables Optimized cGMP Kilogram-Scale Manufacture of Psilocybin Open
A second-generation kilogram-scale synthesis of the psychedelic tryptamine psilocybin has been developed. The synthesis was designed to address several challenges first encountered with the scale-up of previously described literature proce…
View article: Scalable Hybrid Synthetic/Biocatalytic Route to Psilocybin
Scalable Hybrid Synthetic/Biocatalytic Route to Psilocybin Open
Psilocybin, the principal indole alkaloid of Psilocybe mushrooms, is currently undergoing clinical trials as a medication against treatment‐resistant depression and major depressive disorder. The psilocybin supply for pharmaceutical purpos…
View article: Synthesis and Biological Evaluation of Tryptamines Found in Hallucinogenic Mushrooms: Norbaeocystin, Baeocystin, Norpsilocin, and Aeruginascin
Synthesis and Biological Evaluation of Tryptamines Found in Hallucinogenic Mushrooms: Norbaeocystin, Baeocystin, Norpsilocin, and Aeruginascin Open
A general synthetic method was developed to access known tryptamine natural products present in psilocybin-producing mushrooms. In vitro and in vivo experiments were then conducted to inform speculations on the psychoactive properties, or …