Related Experiment Video
Updated: Aug 25, 2026

A Convenient Method for Extraction and Analysis with High-Pressure Liquid Chromatography of Catecholamine Neurotransmitters and Their Metabolites
Published on: March 1, 2018
Conformational requirements for norepinephrine uptake inhibition by phenethylamines in brain synaptosomes. Effects of
Abstract:
Amphetamine is a strong competitive antagonist of brain synaptosomal [3H]norepinephrine ([3H]NE) uptake. Its alpha-ethyl analogue is much less active, while 2-aminotetralin and 1,2-dihydro-2-aminonaphthalene, in which the alpha-ethyl group is tied to the aromatic ring, possess about the same inhibitory potency as amphetamine. The conformational properties of these compounds in solution were studied by 1H and 13C NMR methods. Only small differences between amphetamine and alpha-ethylphenethylamine hydrochlorides were observed in the relative rotamer populations due to rotation around the C alpha -C beta bond of the side chain. In D2O the gauche conformation is slightly favored, while in CDCl3 the trans conformation is the predominant one. Conformational analysis of the alpha-ethyl group in alpha-ethylphenethylamine showed that this group exists in two equally populated conformations in both solvents. It is suggested that these conformations hinder the approach of alpha-ethylphenethylamine to the brain synaptosomal NE uptake sites.
Related Concept Videos
Adrenergic Neurons: Neurotransmission
Synthesis: Catecholamine synthesis requires tyrosine, which is taken...
Adrenergic Agonists: Indirect-Acting Agents
One mechanism involves depleting stored catecholamines by displacing them from synaptic vesicles. These agents, known as "displacers," are transported into vesicles at the expense of noradrenaline. Examples include amphetamine and tyramine, which lack a catechol moiety, resulting in prolonged action, improved oral bioavailability, and...
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...
Adrenergic Antagonists: Chemistry and Classification of ɑ-Receptor Blockers
Nonselective α-blockers: Nonselective α-blockers contain haloalkylamine or imidazoline moieties. Phenoxybenzamine, with a haloalkylamine...
Drugs Affecting Neurotransmitter Release or Uptake
Drugs Affecting Neurotransmitter Synthesis

