Literature DB >> 4009612

Psychotomimetic N-methyl-N-isopropyltryptamines. Effects of variation of aromatic oxygen substituents.

D B Repke, D B Grotjahn, A T Shulgin.   

Abstract

Eight N-methyl-N-isopropyltryptamines (MIPTs) possessing various aromatic oxygen substituents were prepared, characterized, and evaluated for hallucinogenic activity in man. In at least two instances (the Ar H and the Ar 5-OCH3, 1 and 4) the unsymmetrical nitrogen substitution led to a substantial increase in potency as well as oral activity when compared to the symmetrical dimethyl homologues. Qualitatively, 4-hydroxy-N-methyl-N-isopropyltryptamine (2) was the most interesting in overall effect, producing a classic hallucinogenic profile. The 5-methoxy congener 4 resulted in a state characterized by heightened conceptual stimulation lacking in visual phenomena. Other members of the series exhibited diminished effects.

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Year:  1985        PMID: 4009612     DOI: 10.1021/jm00145a007

Source DB:  PubMed          Journal:  J Med Chem        ISSN: 0022-2623            Impact factor:   7.446


  6 in total

Review 1.  The promises and perils of psychedelic pharmacology for psychiatry.

Authors:  Tristan D McClure-Begley; Bryan L Roth
Journal:  Nat Rev Drug Discov       Date:  2022-03-17       Impact factor: 84.694

2.  Chemoenzymatic Synthesis of 5-Methylpsilocybin: A Tryptamine with Potential Psychedelic Activity.

Authors:  Janis Fricke; Alexander M Sherwood; Adam L Halberstadt; Robert B Kargbo; Dirk Hoffmeister
Journal:  J Nat Prod       Date:  2021-03-05       Impact factor: 4.803

3.  The Varieties of the Psychedelic Experience: A Preliminary Study of the Association Between the Reported Subjective Effects and the Binding Affinity Profiles of Substituted Phenethylamines and Tryptamines.

Authors:  Federico Zamberlan; Camila Sanz; Rocío Martínez Vivot; Carla Pallavicini; Fire Erowid; Earth Erowid; Enzo Tagliazucchi
Journal:  Front Integr Neurosci       Date:  2018-11-08

4.  Population Survey Data Informing the Therapeutic Potential of Classic and Novel Phenethylamine, Tryptamine, and Lysergamide Psychedelics.

Authors:  James D Sexton; Charles D Nichols; Peter S Hendricks
Journal:  Front Psychiatry       Date:  2020-02-11       Impact factor: 4.157

Review 5.  Toxicology and Analysis of Psychoactive Tryptamines.

Authors:  Sara Malaca; Alfredo Fabrizio Lo Faro; Alice Tamborra; Simona Pichini; Francesco Paolo Busardò; Marilyn A Huestis
Journal:  Int J Mol Sci       Date:  2020-12-04       Impact factor: 5.923

6.  Horizontal transfer and evolution of transposable elements in vertebrates.

Authors:  Hua-Hao Zhang; Jean Peccoud; Min-Rui-Xuan Xu; Xiao-Gu Zhang; Clément Gilbert
Journal:  Nat Commun       Date:  2020-03-13       Impact factor: 14.919

  6 in total

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