Details
Stereochemistry | ACHIRAL |
Molecular Formula | C8H11N.HI |
Molecular Weight | 249.0921 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
I.NCCC1=CC=CC=C1
InChI
InChIKey=UPHCENSIMPJEIS-UHFFFAOYSA-N
InChI=1S/C8H11N.HI/c9-7-6-8-4-2-1-3-5-8;/h1-5H,6-7,9H2;1H
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 |
|||
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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Following the trace of elusive amines. | 2001 Aug 14 |
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Effects of carboxyl-terminal truncations on the activity and solubility of human monoamine oxidase B. | 2001 Aug 3 |
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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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Biogenic amines in vacuum-packaged and carbon dioxide-controlled atmosphere-packaged fresh pork stored at -1.50 degrees C. | 2001 Feb |
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2-Naphthylamine, a compound found in cigarette smoke, decreases both monoamine oxidase A and B catalytic activity. | 2001 Feb 2 |
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Trace amines: identification of a family of mammalian G protein-coupled receptors. | 2001 Jul 31 |
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A sensitive method for determining levels of [-]-2,5,-dimethoxy-4-methylamphetamine in the brain tissue. | 2001 Jul-Aug |
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Structure-activity studies leading to (-)1-(benzofuran-2-yl)-2-propylaminopentane, ((-)BPAP), a highly potent, selective enhancer of the impulse propagation mediated release of catecholamines and serotonin in the brain. | 2001 May |
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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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Phenibut (beta-phenyl-GABA): a tranquilizer and nootropic drug. | 2001 Winter |
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Probing the catalytic mechanism of Escherichia coli amine oxidase using mutational variants and a reversible inhibitor as a substrate analogue. | 2002 Aug 1 |
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High-performance liquid chromatographic determination of biogenic amines in poultry carcasses. | 2002 Aug 28 |
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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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Stereospecific cleavage of carbon-phosphorus bonds: stereochemical course of the phosphinoyl curtius (Harger) reaction. | 2002 Feb-Mar |
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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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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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[Neuroimaging and neurochemical studies of Rett syndrome]. | 2002 May |
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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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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 |
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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