Skip to content

The Journal of Organic Chemistry

ISSN 0022-3263

18 papers in the library · 593 citations · publishing 1954-2006

Papers

Divinorin A, a psychotropic terpenoid, and divinorin B from the hallucinogenic Mexican mint, Salvia divinorum

The Journal of Organic Chemistry November 1, 1984 Leander J. Valdés, William M. Butler, George M. Hatfield et al. 174 citations

The hallucinogenic Mexican mint Salvia divinorum contains two terpenoid compounds, divinorin A and divinorin B. Divinorin A is a psychotropic terpenoid, while divinorin B is also present. The work describes the isolation and characterization of these compounds from the plant.

DOI: 10.1021/jo00198a026 Hallucinogen Traditional medicine Terpenoid Psychology +2

Improved Fischer Indole Reaction for the Preparation of N,N-Dimethyltryptamines: Synthesis of L-695,894, a Potent 5-HT1D Receptor Agonist

The Journal of Organic Chemistry July 1, 1994 Cheng-Yi Chen, Chris H. Senanayake, Timothy J. Bill et al. 150 citations

The Fischer indole reaction was improved to prepare N,N-dimethyltryptamines, enabling the synthesis of L-695,894, a potent 5-HT1D receptor agonist. The new method provides a more efficient route to this class of compounds.

DOI: 10.1021/jo00092a046 Citation Icon Computer science Social media +3

Synthesis of Tricyclic Heterocycles via a Tandem Aryl Alkylation/Heck Coupling Sequence

The Journal of Organic Chemistry December 29, 2006 Dino Alberico, Alena Rudolph, Mark Lautens 60 citations

A palladium-catalyzed reaction, accelerated by microwave heating, forms two alkyl-aryl bonds and one alkenyl-aryl bond in a single vessel. This method produces a range of symmetrical and unsymmetrical tricyclic heterocycles containing oxygen, nitrogen, silicon, or sulfur atoms, starting from a Heck acceptor and an aryl iodide with two attached alkyl halides. The approach was used to synthesize a tricyclic analogue of mescaline.

DOI: 10.1021/jo0617868 Tandem Tricyclic Aryl Alkylation +10

Abbreviated Ibogaine Congeners. Synthesis and Reactions of Tropan-3-yl-2- and -3-indoles. Investigation of an Unusual Isomerization of 2-Substituted Indoles Using Computational and Spectroscopic Techniques

The Journal of Organic Chemistry April 1, 1994 David B. Repke, Dean R. Artis, Janis T. Nelson et al. 40 citations

The synthesis and reactions of tropan-3-yl-2- and -3-indoles, abbreviated congeners of the psychoactive alkaloid ibogaine, are described. An unusual isomerization of 2-substituted indoles was investigated using computational and spectroscopic techniques. The work provides synthetic routes to these compounds and characterizes the isomerization process, contributing to the chemistry of axial and atropisomeric chirality in alkaloid synthesis.

DOI: 10.1021/jo00087a037 Isomerization Computational chemistry Combinatorial chemistry Organic chemistry +2

MESCALINE ANALOGS. II. TETRA- AND PENTA-METHOXY-β-PHENETHYLAMINES

The Journal of Organic Chemistry January 1, 1955 F. Benington, R. D. Morin, Leland C. Clark 38 citations

The paper reports the synthesis of several tetra- and penta-methoxy-β-phenethylamines, which are analogs of the psychoactive compound mescaline. The authors describe the chemical preparation and characterization of these new compounds, providing details on their synthesis and physical properties. This work contributes to the medicinal chemistry of phenethylamines by expanding the known set of methoxylated derivatives for potential pharmacological study.

DOI: 10.1021/jo01119a017 Mescaline Phenethylamines Tetra Medicinal chemistry

Mescaline Analogs. VIII. Substituted 5-Methoxy-and 5,6,7-Trimethoxyindoles

The Journal of Organic Chemistry January 1, 1958 F. Benington, R. D. Morin, Leland C. Clark 17 citations

This paper reports the synthesis of new mescaline analogs, specifically substituted 5-methoxy- and 5,6,7-trimethoxyindoles. The authors describe the chemical reactions and procedures used to produce these compounds. The work provides details on the preparation and characterization of these organic compounds, contributing to the chemistry of mescaline-related structures.

DOI: 10.1021/jo01095a007 Mescaline Stereochemistry Chemical reaction mechanisms

Mescaline Analogs. V. p-Dialkylamino-β-phenethylamines and 9-(β-Aminoethyl)julolidine

The Journal of Organic Chemistry December 1, 1956 F. Benington, R. D. Morin, L. C. Clark 14 citations

The paper describes the synthesis of a series of p-dialkylamino-β-phenethylamines and the compound 9-(β-aminoethyl)julolidine, which are analogs of mescaline. The authors report the preparation and characterization of these new chemical compounds, including their physical properties and yields. The work contributes to the medicinal chemistry of phenethylamines by expanding the structural diversity of mescaline-like molecules for potential pharmacological study.

DOI: 10.1021/jo01118a038 Mescaline Phenethylamines Medicinal chemistry

MESCALINE ANALOGS. I. 2,4,6-TRIALKOXY-β-PHENETHYLAMINES

The Journal of Organic Chemistry January 1, 1954 F. Benington, R. D. Morin, Leland C. Clark 13 citations

The paper reports the synthesis of a series of 2,4,6-trialkoxy-β-phenethylamines, which are structural analogs of mescaline. The authors describe the chemical preparation and characterization of these compounds, detailing the synthetic routes and analytical data. This work contributes to the chemistry of phenethylamines and provides new compounds for potential pharmacological investigation.

DOI: 10.1021/jo01366a003 Mescaline Phenethylamines Pharmacology Stereochemistry

Stable carbonium ions from .beta.-arylalkyl derivatives in antimony pentafluoride-sulfur dioxide (SbP5.SO2). II. Ions related to mescaline

The Journal of Organic Chemistry May 1, 1974 James A. Manner, James Cook, Brian G. Ramsey 11 citations

In antimony pentafluoride–sulfur dioxide, β-arylalkyl derivatives form stable carbonium ions. This work examines ions related to mescaline, characterizing their structure and stability under these strongly acidic conditions.

DOI: 10.1021/jo00923a007 Carbonium ion Sulfur dioxide Inorganic chemistry

Notes - Mescaline Analogs. IX. Tetra- and Pentamethyl-β-phenethylamines

The Journal of Organic Chemistry December 1, 1958 F. Benington, R Morin, Leland C. Clark 11 citations

The authors report the synthesis of several new mescaline analogs, specifically tetra- and pentamethyl-β-phenethylamines. The work describes the chemical preparation and characterization of these compounds, expanding the known series of mescaline-related structures.

DOI: 10.1021/jo01106a632 Mescaline Phenethylamines Tetra Medicinal chemistry +1

Notes - Mescaline Anaologs. VI. Mescaline Homologs

The Journal of Organic Chemistry December 1, 1956 F. Benington, Robert Morin, Larry Clark 8 citations

The article describes the synthesis of homologs of mescaline, a psychoactive compound. The authors prepared several chemical variants by modifying the carbon chain length of the mescaline molecule. The work focuses on the organic chemistry procedures used to create these analogs, reporting the methods and yields of the synthesized compounds. No biological or pharmacological testing is described in this note.

DOI: 10.1021/jo01118a635 Mescaline Chemistry

MESCALINE ANALOGS. III. 2,4,6-TRIALKYL- AND 3,4-DIHYDROXY-5-METHOXY-β-PHENETHYLAMINES

The Journal of Organic Chemistry September 1, 1955 F. Benington, R. D. Morin, Leland C. Clark 8 citations

This paper reports the synthesis of new mescaline analogs, specifically 2,4,6-trialkyl- and 3,4-dihydroxy-5-methoxy-β-phenethylamines. The authors describe the chemical preparation and characterization of these compounds, expanding the known set of phenethylamine derivatives for potential pharmacological study. No biological testing or activity data are reported in this abstract.

DOI: 10.1021/jo01126a019 Mescaline Phenethylamines Stereochemistry Medicinal chemistry

Bridged Lactones and Bridged Carbocyclic Systems from 2-(3,4,5-Trimethoxyphenyl)-4,5-dimethyl-Δ4-cyclohexenecarboxylic Acid. Novel Mescaline Analogs1

The Journal of Organic Chemistry November 1, 1963 Thomas J. Perun, Leo Zeftel, Robert G. Nelb et al. 5 citations

A series of bridged lactones and bridged carbocyclic compounds were synthesized from 2-(3,4,5-trimethoxyphenyl)-4,5-dimethyl-Δ4-cyclohexenecarboxylic acid, a precursor related to mescaline. The chemical transformations produced novel molecular structures, and the products were analyzed to explore their potential as mescaline analogs.

DOI: 10.1021/jo01046a001 Mescaline Bicyclic molecule Medicinal chemistry Stereochemistry