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Journal of the American Chemical Society

ISSN 1520-5126

14 papers in the library · 474 citations · publishing 1946-2025

Papers

The Alkaloids of Tabernanthe iboga. Part IV.1 The Structures of Ibogamine, Ibogaine, Tabernanthine and Voacangine

Journal of the American Chemical Society January 1, 1958 M. F. Bartlett, D. F. Dickel, W. I. Taylor 131 citations

The paper reports the determination of the structures of four alkaloids—ibogamine, ibogaine, tabernanthine, and voacangine—isolated from the plant Tabernanthe iboga. Through chemical and spectroscopic analysis, the authors establish the molecular frameworks of these compounds, which are central to understanding the plant's psychoactive and medicinal properties. The work provides a foundation for further studies on the pharmacology and synthesis of iboga alkaloids.

DOI: 10.1021/ja01534a036 Citation Computer science Icon Information retrieval +2

Photoelectron spectra of psychotropic drugs. 1. Phenethylamines, tryptamines, and LSD

Journal of the American Chemical Society June 1, 1977 L. N. Domelsmith, Linda L. Munchausen, K. N. Houk 72 citations

The photoelectron spectra of 27 phenethylamines, tryptamines, and LSD were measured and interpreted using semi-empirical molecular orbital calculations. The ionization potentials of these psychotropic drugs correlate with their known pharmacological activities. The spectra provide information about the electronic structures of these molecules, which can be related to their interactions with biological receptors.

DOI: 10.1021/ja00455a018 Tryptamines Phenethylamines Altmetrics Citation +3

Biosynthesis of an Anti-Addiction Agent from the Iboga Plant.

Journal of the American Chemical Society August 21, 2019 Scott C Farrow, Mohamed O Kamileen, Lorenzo Caputi et al. 69 citations

The plant-derived psychoactive compounds (-)-ibogaine and (-)-voacangine show promise for treating opioid addiction but are difficult to obtain from natural sources. Researchers achieved the complete biosynthesis of (-)-voacangine and its de-esterified form, which converts to (-)-ibogaine upon heating, enabling biocatalytic production. These compounds have the opposite enantiomeric configuration compared to other major alkaloids in their class, offering insight into enantioselective enzymatic formal Diels-Alder reactions.

DOI: 10.1021/jacs.9b05999 Full text Substance abuse treatment Anti-addiction agents Opioid dependence solutions Biocatalysis: biocatalytic synthesis +10

Chemical Transformations of Ibogaine

Journal of the American Chemical Society June 1, 1966 G. Büchi, R. E. Manning 34 citations

The paper describes chemical transformations of the alkaloid ibogaine, a compound with psychoactive properties. The authors detail synthetic reactions that modify ibogaine's structure, including oxidation, reduction, and rearrangement processes, producing various derivatives. These transformations are characterized and identified, contributing to the understanding of ibogaine's chemical behavior and potential for generating new compounds. The work is a synthetic organic chemistry study focused on the reactivity and derivatization of ibogaine.

DOI: 10.1021/ja00963a031 Citation Altmetrics Computer science Icon +7

Biosynthesis of the Peyote Alkaloids. The Incorporation of Tyrosine-2-C14 into Mescaline and Anhalonidine1

Journal of the American Chemical Society September 1, 1966 Edward Leete 24 citations

Tyrosine labeled with carbon-14 at the 2-position was fed to peyote plants, and the radioactive label was tracked into the alkaloids mescaline and anhalonidine. The incorporation pattern supports that tyrosine is a precursor in the biosynthesis of these peyote alkaloids, with the label appearing in specific positions consistent with a proposed biosynthetic pathway.

DOI: 10.1021/ja00970a020 Mescaline Citation Icon Social media +7

Photocyclizations of pharmacodynamic amines. V. Unusual rearrangements of the mescaline skeleton

Journal of the American Chemical Society September 1, 1970 Osamu Yonemitsu, Hideo Nakai, Yuichi Kanaoka et al. 20 citations

The mescaline skeleton undergoes unusual rearrangements during photocyclization reactions. Irradiation of certain mescaline derivatives leads to products formed through unexpected bond cleavages and recombinations, rather than simple cyclization. The structures of the photoproducts were determined by spectroscopic methods and X-ray crystallography. The rearrangements involve migration of the trimethoxyphenyl group and formation of new carbon-nitrogen bonds, producing heterocyclic compounds not previously accessible by other routes. These findings illustrate the complexity of photochemical transformations in pharmacologically relevant amines and provide new synthetic pathways to novel ring systems.

DOI: 10.1021/ja00722a025 Mescaline Skeleton computer programming Stereochemistry Radical photochemical reactions

Molecular Design of SERTlight: A Fluorescent Serotonin Probe for Neuronal Labeling in the Brain.

Journal of the American Chemical Society April 10, 2024 Wei-Li Lee, Xavier Westergaard, Christopher Hwu et al. 18 citations

A novel small molecule fluorescent agent called SERTlight specifically labels serotonin neurons in the mammalian brain. SERTlight is a substrate for the serotonin transporter (SERT) and accumulates inside serotonin neurons, producing a bright and selective optical signal. Unlike many other agents, SERTlight does not activate serotonin receptors or other common targets and is not released by neuronal activity or drugs like MDMA. It is compatible with other imaging tools and can label distant axonal projections while allowing simultaneous measurement of serotonin release. This new tool enables detailed study of the serotonin system in health and disease.

DOI: 10.1021/jacs.3c11617 Full text Neuroscience Serotonin research Molecular imaging Brain visualization +1

Photocyclizations of pharmacodynamic amines. III. Three-dimensional structure of 7-hydroxy-1,9,10-trimethoxy-4-azabicyclo[5.2.2]undeca-8,10-dien-3-one from mescaline

Journal of the American Chemical Society July 1, 1969 Osamu Yonemitsu, Hideo Nakai, Yuichi Kanaoka et al. 13 citations

The three-dimensional structure of a photocyclization product derived from mescaline, 7-hydroxy-1,9,10-trimethoxy-4-azabicyclo[5.2.2]undeca-8,10-dien-3-one, was determined by X-ray crystallography. The molecule contains a bicyclic ring system with an azabicyclo[5.2.2]undecane framework, including a ketone and hydroxyl group, and three methoxy substituents. The configuration confirms the stereochemistry resulting from the photochemical reaction of mescaline, a pharmacodynamic amine. This structural elucidation provides insight into the reaction pathway and the three-dimensional arrangement of atoms in the product.

DOI: 10.1021/ja01044a071 Mescaline Pharmacodynamics Stereochemistry Computational chemistry +1

Cactus Alkaloids. II. Condensation of Mescaline with Formaldehyde by the Eschweiler—Clarke Reaction

Journal of the American Chemical Society January 1, 1952 J.a. Rodríguez Castrillón 10 citations

The Eschweiler-Clarke reaction, a reductive methylation using formaldehyde and formic acid, was applied to mescaline, a cactus alkaloid. The reaction produced N-methylmescaline and N,N-dimethylmescaline. The products were isolated and characterized, demonstrating that this condensation method can be used to modify the mescaline molecule. The work provides a synthetic route to N-alkylated derivatives of mescaline, which are of interest for studying structure-activity relationships among cactus alkaloids.

DOI: 10.1021/ja01122a507 Mescaline Cactus Formaldehyde Condensation +1

Ultraviolet Absorption Spectra of Mescaline Sulfate and β-Phenylethylamine Sulfate

Journal of the American Chemical Society November 1, 1946 Kurt Salomon, Albert F. Bina 5 citations

The ultraviolet absorption spectra of mescaline sulfate and β-phenylethylamine sulfate were measured and reported. The data provide reference spectra for these compounds in the ultraviolet range, which can be used for identification and analytical purposes in chemistry and pharmacology.

DOI: 10.1021/ja01215a509 Mescaline Sulfate Ultraviolet Absorption acoustics +4

Deciphering Ibogaine’s Matrix Pharmacology: Multiple Transporter Modulation at Serotonin Synapses

Journal of the American Chemical Society December 26, 2025 Christopher Hwu, Václav Havel, Xavier Westergaard et al. 2 citations

Ibogaine and its main metabolite noribogaine inhibit the vesicular monoamine transporter 2 (VMAT2) with submicromolar potency, as shown in cell-based assays and two-photon microscopy of mouse brain synaptic vesicle clusters. Noribogaine also induces partial serotonin release from synaptic vesicles and binds VMAT2 at a distinct site from the established inhibitor dihydrotetrabenazine. These compounds additionally inhibit plasma membrane monoamine transporters, prominently the serotonin transporter (SERT), and a novel target, organic cation transporter 2 (OCT2). Several iboga analogs display dual inhibition of VMAT2 and SERT with comparable potencies, termed "Synaptic Reuptake Inhibitors" (SynRIs). This profile explains why ibogaine and noribogaine do not induce catalepsy, unlike other VMAT2 inhibitors, and illustrates the complex "matrix pharmacology" of iboga compounds.

DOI: 10.1021/jacs.5c06325 Serotonergic Monoamine neurotransmitter Serotonin transporter Vesicular monoamine transporter +10