Synthesis and structural insights into novel quaternary tryptamine analogues: a thesis in Chemistry

Harsh Bawa

doi:10.62791/20671

Back

Thesis

Synthesis and structural insights into novel quaternary tryptamine analogues: a thesis in Chemistry

Harsh Bawa

Master of Science (MS), University of Massachusetts Dartmouth

2026

DOI:

https://doi.org/10.62791/20671

Abstract

Tryptamine natural products, particularly serotonin, play important physiological roles and function as neurotransmitters in mediating mood in humans through their interactions with serotonin receptors, which are distributed throughout the central and peripheral nervous systems. While serotonin controls mood in the central nervous system, a vast majority of it is found in peripheral locations, particularly the digestive tract. There are many tryptamine natural products found in nature, including a variety of compounds that are maximally alkylated to generate quaternary tryptamines, which, due to their charged nature, are unlikely to cross the blood-brain barrier. What (if any) role do these peripherally restricted compounds play? In this work/research study, novel analogues of quaternary tryptammonium salts are synthesized and characterized using nuclear magnetic resonance (NMR) spectroscopy and single-crystal X-ray crystallography to advance the understanding of their impact.

Files and links (1)

pdf

Bawa H. CAS MS Thesis 20262.92 MB

Embargoed Access, Embargo ends: 09/21/2027 CC BY-NC-ND V4.0

Metrics

2 Record Views

Details

Title: Synthesis and structural insights into novel quaternary tryptamine analogues
Creators: Harsh Bawa
ORCID: 0009-0008-4463-436X
Contributors: David Robert Manke (Advisor) - University of Massachusetts Dartmouth, Department of Chemistry and Biochemistry
Catherine Neto (Committee Member) - University of Massachusetts Dartmouth, Department of Chemistry and Biochemistry
Shuowei Cai (Committee Member) - University of Massachusetts Dartmouth, Department of Chemistry and Biochemistry
Number of pages: x, 96 pages
Illustrations: illustrations
Table of contents: List of figures -- List of tables -- Background and significance -- Tryptamines -- Serotonin -- Traditional psychoactive tryptamines -- Ayahuasca -- Toad venom -- Magic mushrooms -- Experiments and results -- Synthesis of N-isopropyl-N, N-dimethyltryptammonium iodide (DMiPT I) -- Synthesis of N-isopropyl-N, N-dimethyltryptammonium iodide (DEiPT I) -- Synthesis of N-methyll-N, N-diisopropyltryptammonium iodide (MDiPT I) -- Synthesis of 2-methyl-N-isopropyl-N, N-dimethyltryptammonium iodide (2-Me-DEiPT I) -- Synthesis of 2-methyl-N-isopropyl-N, N-diethyltryptammonium iodide (2-Me-DEiPT I) -- Synthesis of 5-methyl-N-N-diisopropytryptammonium Iodide (5-Me-DiPT I) -- Synthesis of 5-methoxy-N-isopropy-N,N-dimethyltryptammonium Iodide (5-MeODMiPT I) -- Synthesis of 5-methoxy-N-isopropy-N,N-diethyltryptammonium Iodide (5-MeODEiPT I) -- Synthesis of 5-chloro-N-isopropy-N,N-diethyltryptammonium Iodide (5-Cl-DEiPT I) -- Synthesis of 5-chloro-N-isopropytryptammonium chloride (5-Cl-NiPT Cl) -- Synthesis of 5-chloro-N-methyl-N,N-isopropytryptammonium iodide (5-Cl-MDiPT I) -- Synthesis of 6-floro-N-isopropy-N,N-diethyltryptammonium iodide (6-F-DEiPT I) -- Synthesis of 6-methyltryptammonium chloride (6-Me-T Cl) -- Synthesis of Co-crystal (5-Me-DMiPT I + 5-Me-MDiPT I) -- Synthesis of Co-crystal (DMiPT I + MDiPT I) -- Discussion -- Future directions -- References.
References: Includes bibliographical references (pages 89-96).
Awarding Institution: University of Massachusetts Dartmouth
Degree Awarded: Master of Science (MS)
Degree in: Chemistry
Academic Unit: Department of Chemistry and Biochemistry
Language: English
Resource Type: Thesis
DOI: https://doi.org/10.62791/20671
Record Identifier: 9914554690601301