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Receptor binding profiles and quantitative structure-affinity relationships of some

Nicholas V Cozzi1, Paul F Daley2

  • 1The Alexander Shulgin Research Institute, 1483 Shulgin Road, Lafayette, CA 94549, United States; Neuropharmacology Laboratory, 2695 Medical Sciences Center, Department of Cell and Regenerative Biology, University of Wisconsin School of Medicine and Public Health, 1300 University Avenue, Madison, WI 53706, United States.

Bioorganic & Medicinal Chemistry Letters
|January 8, 2016
PubMed
Summary

This study explored the pharmacological profiles of N,N-diallyltryptamine (DALT) and its derivatives, identifying numerous receptor targets. These findings suggest multiple serotonin and non-serotonergic sites contribute to the psychoactive effects of DALT compounds.

Keywords:
5-Methoxy-N,N-diallyltryptamineDALTHallucinogenN,N-DiallyltryptaminePsychedelicPsychopharmacologyQSARReceptor bindingTryptamine

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Area of Science:

  • Pharmacology
  • Medicinal Chemistry
  • Neuroscience

Background:

  • N,N-Diallyltryptamine (DALT) and 5-methoxy-N,N-diallyltryptamine (5-MeO-DALT) are psychoactive tryptamines with poorly characterized pharmacological properties.
  • Previous research by Alexander Shulgin indicated differing psychoactivity levels between DALT and 5-MeO-DALT.

Purpose of the Study:

  • To synthesize and characterize novel 5-substituted-DALT compounds.
  • To evaluate the binding affinities of DALT and its derivatives at various cloned receptors and transporter proteins.
  • To identify potential structure-affinity relationships within the 5-substituted-DALT series.

Main Methods:

  • Synthesis of novel 5-substituted-N,N-diallyltryptamines.
  • In vitro binding assays against 45 cloned receptors and transporter proteins.
  • Quantitative structure-activity relationship (QSAR) analysis using electronic, hydrophobic, and steric parameters.

Main Results:

  • Identified 27 potential receptor targets for 5-substituted-DALT compounds based on in vitro binding affinities.
  • Observed nanomolar affinities for serotonin receptors (5-HT1A, 5-HT1D, 5-HT2B, 5-HT6, 5-HT7), adrenergic receptors (α2A, α2B, α2C), sigma receptors (σ1, σ2), and histamine H1 receptors.
  • Established correlations between physicochemical properties (steric volume, electronic, hydrophobic parameters) and binding affinities at specific receptors.

Conclusions:

  • Multiple serotonin and non-serotonergic targets are likely involved in the psychoactive effects of DALT drugs.
  • Quantitative structure-affinity relationships were identified, aiding in the rational design of more potent and selective DALT analogs.
  • The study provides a foundation for further investigation into the therapeutic potential and mechanisms of action of DALT derivatives.