Related Experiment Video
Updated: May 9, 2026

Preparation of Stable Bicyclic Aziridinium Ions and Their Ring-Opening for the Synthesis of Azaheterocycles
Published on: August 22, 2018
Effect of ring-constrained phenylpropyloxyethylamines on sigma receptors
Lidiya Stavitskaya1, Michael J Seminerio, Jason R Healy
1Department of Pharmaceutical Sciences, University of Maryland, School of Pharmacy, 20 N. Pine Street, Baltimore, MD 21201, USA.
Abstract:
A series of ring-constrained phenylpropyloxyethylamines, partial opioid structure analogs and derivatives of a previously studied sigma (σ) receptor ligand, was synthesized and evaluated at σ and opioid receptors for receptor selectivity. The results of this study identified several compounds with nanomolar affinity at both σ receptor subtypes. Compounds 6 and 9 had the highest selectivity for both σ receptor subtypes, compared to μ opioid receptors. In addition, compounds 6 and 9 significantly reduced the convulsive effects of cocaine in mice, which would be consistent with antagonism of σ receptors.
More Related Videos
07:16Methods for the Discovery of Novel Compounds Modulating a Gamma-Aminobutyric Acid Receptor Type A Neurotransmission
Published on: August 16, 2018
10:42Preparation of N-(2-alkoxyvinyl)sulfonamides from N-tosyl-1,2,3-triazoles and Subsequent Conversion to Substituted Phthalans and Phenethylamines
Published on: January 3, 2018
Related Concept Videos
Adrenergic Agonists: Chemistry and Structure-Activity Relationship
Aromatic ring substitutions: Substituting the aromatic ring with –OH groups at positions 3 and 4 yields catecholamines (e.g., epinephrine), which have a high affinity for adrenoceptors. Hydrogen bonding between –OH groups and receptors enhances adrenergic activity.
Separation of the aromatic...
ortho–para-Directing Activators: –CH3, –OH, –⁠NH2, –OCH3
π Electron Effects on Chemical Shift: Aromatic and Antiaromatic Compounds
Base-Catalyzed Ring-Opening of Epoxides
Acid-Catalyzed Ring-Opening of Epoxides
Directing Effect of Substituents: meta-Directing Groups