Details
Stereochemistry | ACHIRAL |
Molecular Formula | C8H11N.HNO3 |
Molecular Weight | 184.1925 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
O[N+]([O-])=O.NCCC1=CC=CC=C1
InChI
InChIKey=OSPDPBJTCYRCLZ-UHFFFAOYSA-N
InChI=1S/C8H11N.HNO3/c9-7-6-8-4-2-1-3-5-8;2-1(3)4/h1-5H,6-7,9H2;(H,2,3,4)
β-phenylethylamine (2-phenylethylamine) is a small amine containing alkaloid synonymous with phenethylamine and the acronym PEA; in the human body it has a neuromodulator/neurotransmitter role and is known as a trace amine due to its low quantity relative to other bioactive amino acids. PEA was characterized as a substrate for type B monoamine oxidase. PEA functions by activating trace amine receptors (including TAAR1 and TAAR2) thereby regulating monoamine turnover. Ring-substituted phenethylamines, commonly known as 2Cs, are designer drugs that are emerging as new drugs of abuse. PEA administration may be therapeutic in selected depressed patients.
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
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Target ID: CHEMBL2039 Sources: https://www.ncbi.nlm.nih.gov/pubmed/7205271 |
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Target ID: CHEMBL5857 |
0.3 µM [EC50] | ||
Target ID: Q9P1P5 Gene ID: 9287.0 Gene Symbol: TAAR2 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/27424325 |
0.43 nM [EC50] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Primary | Unknown Approved UseUnknown |
PubMed
Title | Date | PubMed |
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Psychomotor stimulant effects of beta-phenylethylamine in monkeys treated with MAO-B inhibitors. | 2001 Dec |
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Neurobiology and neurochemistry of Rett syndrome. | 2001 Dec |
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Amphetamine, 3,4-methylenedioxymethamphetamine, lysergic acid diethylamide, and metabolites of the catecholamine neurotransmitters are agonists of a rat trace amine receptor. | 2001 Dec |
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Loss of serotonin oxidation as a component of the altered substrate specificity in the Y444F mutant of recombinant human liver MAO A. | 2001 Dec 11 |
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Apomorphine, dopamine and phenylethylamine reduce the proportion of phosphorylated insulin receptor substrate 1. | 2001 Dec 14 |
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Spectroscopic observation of intermediates formed during the oxidative half-reaction of copper/topa quinone-containing phenylethylamine oxidase. | 2001 Dec 25 |
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Poly(amidoamine)s as potential nonviral vectors: ability to form interpolyelectrolyte complexes and to mediate transfection in vitro. | 2001 Fall |
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I1 receptors, cardiovascular function, and metabolism. | 2001 Nov |
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Biochemical, behavioral, physiologic, and neurodevelopmental changes in mice deficient in monoamine oxidase A or B. | 2001 Nov 15 |
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Oxidation of phenethylamine derivatives by cytochrome P450 2D6: the issue of substrate protonation in binding and catalysis. | 2001 Nov 27 |
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Fluorometric determination of DL-fenfluramine, DL-norfenfluramine and phentermine in plasma by achiral and chiral high-performance liquid chromatography. | 2001 Nov 5 |
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Inhibition of copper amine oxidases by pyridine-derived aldoximes and ketoximes. | 2001 Nov-Dec |
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A TLC visualisation reagent for dimethylamphetamine and other abused tertiary amines. | 2001 Oct-Dec |
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Phenibut (beta-phenyl-GABA): a tranquilizer and nootropic drug. | 2001 Winter |
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The enigma of conditioned taste aversion learning: stimulus properties of 2-phenylethylamine derivatives. | 2002 |
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An MCASE approach to the search of a cure for Parkinson's Disease. | 2002 Apr 2 |
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Intercalated organic-inorganic perovskites stabilized by fluoroaryl-aryl interactions. | 2002 Apr 22 |
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[Human striatal D-neurons and their significance]. | 2002 Aug |
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Subjective and hormonal effects of 3,4-methylenedioxymethamphetamine (MDMA) in humans. | 2002 Aug |
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Content of biogenic amines in a Chardonnay wine obtained through spontaneous and inoculated fermentations. | 2002 Aug 14 |
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High-performance liquid chromatographic determination of biogenic amines in poultry carcasses. | 2002 Aug 28 |
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[Localization of non-monoaminergic aromatic L-amino acid decarboxylase neurons (D-neurons) in the human striatum and their functional significance]. | 2002 Dec |
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Synthesis of 3-alkyl(aryl)-4-alkylidenamino-4,5-dihydro-1H-1,2,4-triazol-5-ones and 3-alkyl-4-alkylamino-4,5-dihydro-1H-1,2,4-triazol-5-ones as antitumor agents. | 2002 Dec |
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The effects of acute and subchronic treatment with fluoxetine and citalopram on stimulus control by DOM. | 2002 Dec |
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Analysis of enantiomers of chiral phenethylamine drugs by capillary gas chromatography/mass spectrometry/flame-ionization detection and pre-column chiral derivatization. | 2002 Dec 31 |
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High-level expression of human liver monoamine oxidase A in Pichia pastoris: comparison with the enzyme expressed in Saccharomyces cerevisiae. | 2002 Feb |
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Stereospecific cleavage of carbon-phosphorus bonds: stereochemical course of the phosphinoyl curtius (Harger) reaction. | 2002 Feb-Mar |
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Automated headspace solid-phase microextraction and in-matrix derivatization for the determination of amphetamine-related drugs in human urine by gas chromatography-mass spectrometry. | 2002 Jan |
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Enzymatic decarboxylation of tyrosine and phenylalanine to enhance volatility for high-precision isotopic analysis. | 2002 Jan 15 |
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Do we know the mechanism of chiral recognition between cyclodextrins and analytes? | 2002 Jan 15 |
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Characterization of selected Spanish table wine samples according to their biogenic amine content from liquid chromatographic determination. | 2002 Jul 31 |
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Monoamine-dependent production of reactive oxygen species catalyzed by pseudoperoxidase activity of human hemoglobin. | 2002 Jun |
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Application of ligand SAR, receptor modeling and receptor mutagenesis to the discovery and development of a new class of 5-HT(2A) ligands. | 2002 Jun |
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Rat striatal monoamine oxidase-B inhibition by l-deprenyl and rasagiline: its relationship to 2-phenylethylamine-induced stereotypy and Parkinson's disease. | 2002 Mar |
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Increased baroreceptor response in mice deficient in monoamine oxidase A and B. | 2002 Mar |
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Cp*(2)TiMe(2): an improved catalyst for the intermolecular addition of n-alkyl- and benzylamines to alkynes. | 2002 Mar 22 |
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[Decreased beta-phenylethylamine in urine of children with attention deficit hyperactivity disorder and autistic disorder]. | 2002 May |
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Heart rate dynamics in monoamine oxidase-A- and -B-deficient mice. | 2002 May |
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Analysis of conserved active site residues in monoamine oxidase A and B and their three-dimensional molecular modeling. | 2002 May 10 |
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Simultaneous separation of common mono- and divalent cations on a calcinated silica gel column by ion chromatography with indirect photometric detection and aromatic monoamines-oxalic acid, containing crown ethers, used as eluent. | 2002 May 17 |
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[Tetrahydroisoquinoline derivatives as possible Parkinson's disease-inducing substances]. | 2002 Nov |
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Novel dual inhibitors of AChE and MAO derived from hydroxy aminoindan and phenethylamine as potential treatment for Alzheimer's disease. | 2002 Nov 21 |
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Production of amines in equine cecal contents in an in vitro model of carbohydrate overload. | 2002 Oct |
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Major depressive episodes and diet pills. | 2002 Oct |
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Plausible molecular mechanism for activation by fumarate and electron transfer of the dopamine beta-mono-oxygenase reaction. | 2002 Oct 1 |
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Increased urine phenylethylamine after methylphenidate treatment in children with ADHD. | 2002 Sep |
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Stimulation of the catecholaminergic and serotoninergic neurons in the rat brain by R-(-)-1-(benzofuran-2-yl)-2-propylaminopentane, (-)-BPAP. | 2002 Sep 20 |
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Degradation of benzyldimethylalkylammonium chloride by Aeromonas hydrophila sp. K. | 2003 |
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Serotonin 5-hydroxytryptamine 2A receptor-coupled phospholipase C and phospholipase A2 signaling pathways have different receptor reserves. | 2003 Jan |
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Role of copper ion in bacterial copper amine oxidase: spectroscopic and crystallographic studies of metal-substituted enzymes. | 2003 Jan 29 |
Sample Use Guides
Early research shows that taking 10-60 mg of phenethylamine by mouth per day along with 5 mg of the antidepressant selegiline (Anipryl, Eldepryl) twice per day for 4 weeks relieves depression in 60% of people. Of the people who respond to initial treatment with phenethylamine plus selegiline, 86% show continued depression relief when treated for up to 50 weeks.
Excretion study of phenethylamine in man: single oral dose of 300 mg.
Rats: 20, 40, 100 mg/kg ip or 1.0, 2.5, and 5.0 mg/kg iv
Route of Administration:
Other
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/18182557
1 uM phenethylamine alters monoamine transporter function in vitro
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SUBSTANCE RECORD