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Forensic Science International Dec 2001The possibility of simultaneous synthesis of alpha-phenylethylamine and amphetamine from mixture of acetophenone and benzylmethylketone was studied. The structures of...
The possibility of simultaneous synthesis of alpha-phenylethylamine and amphetamine from mixture of acetophenone and benzylmethylketone was studied. The structures of specific impurities were predicted and these compounds were synthesized and finally found in reaction mixtures, as well as in the final product. The data collected by gas chromatography, proton and carbon magnetic resonance, Fourier transform infrared spectrometry and mass spectrometry are presented.
Topics: Amphetamines; Chromatography, Gas; Drug Contamination; Gas Chromatography-Mass Spectrometry; Illicit Drugs; Phenethylamines; Spectrophotometry, Infrared
PubMed: 11728746
DOI: 10.1016/s0379-0738(01)00548-5 -
The Kurume Medical Journal 2000Plasma beta-phenylethylamine (PEA) levels were determined in 27 patients with Parkinson's disease (PD) in order to evaluate its relation with the severity or clinical...
Plasma beta-phenylethylamine (PEA) levels were determined in 27 patients with Parkinson's disease (PD) in order to evaluate its relation with the severity or clinical course of PD. The plasma PEA concentrations in PD patients were significantly lower (mean +/- SD, 862 +/- 554 pg/ml) than those in the control group (1765 +/- 790 pg/ml) (p < 0.0001). The concentrations of PEA in plasma did not correlate with Hoen and Yahr stage. However, in serial measurements of the PEA of 5 patients in the progressive group of the clinical course of PD, the plasma PEA levels revealed a downward trend after one or two years. On the other hand, in 3 patients of non-progressive group, the plasma PEA remained at the same level. This study suggests that plasma PEA level might reflect nigrostriatal degeneration in patients with PD.
Topics: Aged; Female; Gas Chromatography-Mass Spectrometry; Humans; Male; Middle Aged; Parkinson Disease; Phenethylamines
PubMed: 11197147
DOI: 10.2739/kurumemedj.47.267 -
Yakubutsu, Seishin, Kodo = Japanese... Sep 1986beta Phenylethylamine (PEA) is an endogenous amine that resembles amphetamine in chemical structure and has been identified in human and other mammalian brains and in... (Review)
Review
beta Phenylethylamine (PEA) is an endogenous amine that resembles amphetamine in chemical structure and has been identified in human and other mammalian brains and in many peripheral tissues. Although PEA exists in much smaller amounts than monoamines, the mode of action of PEA as a neuromodulator is of special interest. In this paper the author reviews animal and clinical studies on PEA. The first section deals the methods for the determination of PEA in mammalian brains and human urine. PEA is reliably measured using spectrofluorometric, gas chromatographic-mass spectrometric methods. The second chapter reviews the changes in animal behavior elicited by PEA. The administration of PEA induces stereotypy and increased motor activity in animals. The third part reviews the effect of PEA on dopamine, noradrenaline, serotonin and tyramine metabolism in mammalian brains. The fourth chapter examines recent clinical evidence suggesting a role for PEA in schizophrenia and affective disorders.
Topics: Animals; Behavior, Animal; Biogenic Amines; Brain; Haplorhini; Humans; Mice; Phenethylamines; Psychotropic Drugs; Rats
PubMed: 3101312
DOI: No ID Found -
Lloydia 1977A total of ten alkaloids have been identified in extracts of a Mexican cactus, Dolichothele uberiformis (Zucc.) Br. and R. The data provide documentation for the...
A total of ten alkaloids have been identified in extracts of a Mexican cactus, Dolichothele uberiformis (Zucc.) Br. and R. The data provide documentation for the presence of (--)-synephrine, (--)-longimammine, N-methyl-3,4-dimethoxy-beta-phenethylamine, N-methyl-4-methoxy-beta-phenethylamine, (--y-normacromerine, N-methyltryramine, hordenine, longimammatine, and the first reported isolation of (--)-N,N-dimethyl-beta-hydroxy-beta-phenethylamine (ubine) from a natural source. Spectral data support the identification of another new alkaloid (uberine) as 5-methoxy-7-hydroxy-2-methyl-1,2,3,4-tetrahydroisoquinoline.
Topics: Desert Climate; Isoquinolines; Mexico; Phenethylamines; Plants; Species Specificity; Tetrahydroisoquinolines
PubMed: 875645
DOI: No ID Found -
Journal of Neurochemistry Nov 1995The adrenal medullary chromaffin cell is a commonly used model for the adrenergic neuron. Although much work has been done to study the transport system in the adrenal...
The adrenal medullary chromaffin cell is a commonly used model for the adrenergic neuron. Although much work has been done to study the transport system in the adrenal chromaffin vesicles, relatively little is known about cellular transport, especially with regard to structural features of phenethylamines required for intracellular accumulation. We have now investigated the structural requirements of phenethylamine-related compounds for their accumulation into cultured adrenal chromaffin cells. We find that two types of cellular uptake, previously described only for dopamine, norepinephrine, and epinephrine, are also present for [3H]tyramine. Although two types of accumulation occur, tyramine accumulation occurs mainly via a cocaine-insensitive process, whereas dopamine accumulation occurs predominantly via a cocaine-sensitive process. The accumulation of [14C]-phenethylamine and p-methoxyphenethylamine is not affected by cocaine, suggesting that a ring hydroxyl substituent is necessary for cocaine-sensitive accumulation. The compounds p-hydroxyphenylpropylamine and p-hydroxyphenyl-2-aminoethyl sulfide accumulate in the cell only via a cocaine-insensitive process, indicating that lengthening of the aminoalkyl side chain prevents cocaine-sensitive accumulation. We have performed conformational analyses of this series of compounds to determine whether the conformation of these compounds can be related to the kinetic data. For dopamine, tyramine, phenethylamine, and p-methoxyphenethylamine, two groups of energy-minimized conformers were found. We find that there is an approximately linear relationship between the Km values for these phenethylamines and the differences in minimized energies between the low- and highest energy conformer groups of each compound. A similar correlation was found for p-hydroxyphenyl-2-aminoethyl sulfide. These results are consistent with the hypothesis that these compounds undergo a conformational change from the low-energy conformer to the highest energy conformer before their cocaine-insensitive accumulation.
Topics: Adrenal Glands; Animals; Cattle; Cells, Cultured; Chromaffin System; Cocaine; Dopamine; Molecular Conformation; Phenethylamines; Tyramine
PubMed: 7595487
DOI: 10.1046/j.1471-4159.1995.65052031.x -
Journal of the American Chemical Society May 2022Fluorine-containing medicinal compounds frequently allow modulation of physical-chemical properties. Here, we address the effect of fluorine, near the ethylamino side...
Fluorine-containing medicinal compounds frequently allow modulation of physical-chemical properties. Here, we address the effect of fluorine, near the ethylamino side chain, on conformational flexibility and noncovalent interactions (NCIs) of the selected jet-cooled monohydrated cluster of 2-(2-fluoro-phenyl)-ethylamine (2-FPEA) by mass-selected resonance-enhanced two-photon ionization and ionization-loss stimulated Raman spectroscopies. Our results show that Raman spectral signatures of the 2-FPEA-HO cluster match the scaled harmonic vibrational Raman frequencies, resulting from density functional theory calculations of the most stable 2-FPEA conformer hydrogen-bonded (HB) to water, confirming the three-dimensional cluster structure. This predicted electronic structure, together with NCI analysis, allows visualization and assessment of the attractive and repulsive interactions. The comparison of the NCIs and revealed red (O-H and N-H stretches) and blue shifts (C-H stretches and CH out-of-plane bends) of the cluster to other class members confirm O-H···N, N-H···π, C-H···O, and C-H···F HB formation and their contribution to structure stabilization, uncovering the potential of the approach.
Topics: Fluorine; Hydrogen Bonding; Molecular Conformation; Phenethylamines
PubMed: 35471862
DOI: 10.1021/jacs.2c02480 -
Progress in Neuro-psychopharmacology &... 19891. The relevance of trace amine research is outlined for PEA and T in the context of psychotherapeutic drug action, particularly in relation to the actions of... (Review)
Review
1. The relevance of trace amine research is outlined for PEA and T in the context of psychotherapeutic drug action, particularly in relation to the actions of MAO-inhibitor antidepressant drugs. 2. Evidence for the neuronal localization of these amines and their relationship to brain catecholamines is discussed with respect to possible co-localization with DA and their distribution within the nigro-striatal/striato-nigral system. 3. The results of recent experiments assessing the behavioural effects of prodrugs for PEA and T are described. The interactions of these compounds with MAO inhibitors are assessed and the actions of PEA prodrugs are discussed in relation to brain DA systems. 4. Recent evidence for functional decreases in beta-adrenergic receptors following chronic administration of MAO inhibitors is outlined. The lack of association of such effects with the percentage of MAO inhibition observed after these treatments indicates influences of these compounds (or metabolites) on factors other than MAO activity as mediators of these effects. The possible role of PEA (as a metabolite of PLZ) in this context is proposed. The possible involvement of PEA in emergent changes in beta-adrenergic receptors induced by chronic antidepressant drugs is hypothesized in relation to ongoing research.
Topics: Animals; Brain; Catecholamines; Phenethylamines; Prodrugs; Psychotropic Drugs; Tryptamines
PubMed: 2664894
DOI: 10.1016/0278-5846(89)90131-0 -
Biochemical and Biophysical Research... Dec 1981
Topics: Animals; Behavior, Animal; Brain; Catecholamines; Ditiocarb; Methysergide; Phenethylamines; Pimozide; Polyribosomes; Rats; Serotonin
PubMed: 6277320
DOI: 10.1016/0006-291x(81)90922-0 -
Chemical Communications (Cambridge,... Feb 2015A copper-catalyzed regio- and intermolecular aminofluorination of styrenes has been developed. In this reaction Ph-I=N-Ts and Et3N·3HF act as nitrogen and fluorine...
A copper-catalyzed regio- and intermolecular aminofluorination of styrenes has been developed. In this reaction Ph-I=N-Ts and Et3N·3HF act as nitrogen and fluorine sources, respectively. The obtained β-fluoro-N-Ts-phenethylamines can be N-alkylated with subsequent deprotection affording the corresponding β-fluoro-N-alkylated phenethylamines, which are interesting building blocks for compounds acting on neuronal targets.
Topics: Catalysis; Copper; Fluorine; Phenethylamines; Stereoisomerism; Styrenes
PubMed: 25622147
DOI: 10.1039/c4cc10162f -
The Journal of Organic Chemistry Nov 2017The first total synthesis of dendrochrysanene (1) was achieved. The key reaction for the construction of dendrochrysanene was an oxidative frame rearrangement reaction...
The first total synthesis of dendrochrysanene (1) was achieved. The key reaction for the construction of dendrochrysanene was an oxidative frame rearrangement reaction from a phenanthrene dimer to a spiro-lactone skeleton, which we serendipitously identified. Owing to the steric hindrance of the substituent on the peri position of the phenanthrene dimer, high-temperature conditions were required for the rearrangement reaction; however, at such temperatures, the substrate decomposed. To address this issue, we added phenylethylamine or benzylamine to the reaction system. We assumed that the amine trapped generated hydrochloric acid and acted as a ligand for iron, helping to maintain an appropriate redox potential. The total synthesis of dendrochrysanene, involving this rearrangement reaction, is an important sequence interlinking phenanthrene derivatives, phenanthrene dimers, and spiro-lactone compounds, which are frequently isolated from plants of Orchidaceae.
Topics: Benzylamines; Dendrobium; Molecular Structure; Phenanthrenes; Phenethylamines; Spiro Compounds
PubMed: 28967251
DOI: 10.1021/acs.joc.7b02223