Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C8H11N |
| Molecular Weight | 121.1796 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
NCCC1=CC=CC=C1
InChI
InChIKey=BHHGXPLMPWCGHP-UHFFFAOYSA-N
InChI=1S/C8H11N/c9-7-6-8-4-2-1-3-5-8/h1-5H,6-7,9H2
| Molecular Formula | C8H11N |
| Molecular Weight | 121.1796 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
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
PubMed
| Title | Date | PubMed |
|---|---|---|
| Neurobiology and neurochemistry of Rett syndrome. | 2001 Dec |
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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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| A sensitive method for determining levels of [-]-2,5,-dimethoxy-4-methylamphetamine in the brain tissue. | 2001 Jul-Aug |
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| A molecular approach to the study of structure-activity correlation for some amphetamines. | 2001 Jul-Sep |
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| I1 receptors, cardiovascular function, and metabolism. | 2001 Nov |
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| Hydrogen-deuterium exchange at non-labile sites: a new reaction facet with broad implications for structural and dynamic determinations. | 2001 Nov |
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| Apical dominance in Pssu-ipt-transformed tobacco. | 2001 Nov |
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| Platelet monoamine oxidase in healthy 9- and 15-years old children: the effect of gender, smoking and puberty. | 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 |
|
| Inhibition of copper amine oxidases by pyridine-derived aldoximes and ketoximes. | 2001 Nov-Dec |
|
| A TLC visualisation reagent for dimethylamphetamine and other abused tertiary amines. | 2001 Oct-Dec |
|
| The enigma of conditioned taste aversion learning: stimulus properties of 2-phenylethylamine derivatives. | 2002 |
|
| Geometry-affinity relationships of the selective serotonin receptor ligand 9-(aminomethyl)-9,10-dihydroanthracene. | 2002 Apr 11 |
|
| An MCASE approach to the search of a cure for Parkinson's Disease. | 2002 Apr 2 |
|
| Intercalated organic-inorganic perovskites stabilized by fluoroaryl-aryl interactions. | 2002 Apr 22 |
|
| [Human striatal D-neurons and their significance]. | 2002 Aug |
|
| Subjective and hormonal effects of 3,4-methylenedioxymethamphetamine (MDMA) in humans. | 2002 Aug |
|
| Probing the catalytic mechanism of Escherichia coli amine oxidase using mutational variants and a reversible inhibitor as a substrate analogue. | 2002 Aug 1 |
|
| Content of biogenic amines in a Chardonnay wine obtained through spontaneous and inoculated fermentations. | 2002 Aug 14 |
|
| High-performance liquid chromatographic determination of biogenic amines in poultry carcasses. | 2002 Aug 28 |
|
| [Localization of non-monoaminergic aromatic L-amino acid decarboxylase neurons (D-neurons) in the human striatum and their functional significance]. | 2002 Dec |
|
| 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 |
|
| The effects of acute and subchronic treatment with fluoxetine and citalopram on stimulus control by DOM. | 2002 Dec |
|
| Analysis of enantiomers of chiral phenethylamine drugs by capillary gas chromatography/mass spectrometry/flame-ionization detection and pre-column chiral derivatization. | 2002 Dec 31 |
|
| Enzymatic decarboxylation of tyrosine and phenylalanine to enhance volatility for high-precision isotopic analysis. | 2002 Jan 15 |
|
| 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 |
|
| Monoamine oxidase A and B activities in embryonic chick hepatocytes: differential regulation by retinoic acid. | 2002 Jun |
|
| Rat striatal monoamine oxidase-B inhibition by l-deprenyl and rasagiline: its relationship to 2-phenylethylamine-induced stereotypy and Parkinson's disease. | 2002 Mar |
|
| Increased baroreceptor response in mice deficient in monoamine oxidase A and B. | 2002 Mar |
|
| Cp*(2)TiMe(2): an improved catalyst for the intermolecular addition of n-alkyl- and benzylamines to alkynes. | 2002 Mar 22 |
|
| [Neuroimaging and neurochemical studies of Rett syndrome]. | 2002 May |
|
| Heart rate dynamics in monoamine oxidase-A- and -B-deficient mice. | 2002 May |
|
| Analysis of conserved active site residues in monoamine oxidase A and B and their three-dimensional molecular modeling. | 2002 May 10 |
|
| 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 |
|
| [Tetrahydroisoquinoline derivatives as possible Parkinson's disease-inducing substances]. | 2002 Nov |
|
| Novel dual inhibitors of AChE and MAO derived from hydroxy aminoindan and phenethylamine as potential treatment for Alzheimer's disease. | 2002 Nov 21 |
|
| Production of amines in equine cecal contents in an in vitro model of carbohydrate overload. | 2002 Oct |
|
| Major depressive episodes and diet pills. | 2002 Oct |
|
| Plausible molecular mechanism for activation by fumarate and electron transfer of the dopamine beta-mono-oxygenase reaction. | 2002 Oct 1 |
|
| Formation of biogenic amines in a typical semihard Italian cheese. | 2002 Sep |
|
| Increased urine phenylethylamine after methylphenidate treatment in children with ADHD. | 2002 Sep |
|
| 1-(Benzofuran-2-yl)-2-(3,3,3-trifluoropropyl)aminopentane HCl, 3-F-BPAP, antagonizes the enhancer effect of (-)-BPAP in the shuttle box and leaves the effect of (-)-deprenyl unchanged. | 2002 Sep 13 |
|
| Stimulation of the catecholaminergic and serotoninergic neurons in the rat brain by R-(-)-1-(benzofuran-2-yl)-2-propylaminopentane, (-)-BPAP. | 2002 Sep 20 |
|
| Degradation of benzyldimethylalkylammonium chloride by Aeromonas hydrophila sp. K. | 2003 |
|
| Serotonin 5-hydroxytryptamine 2A receptor-coupled phospholipase C and phospholipase A2 signaling pathways have different receptor reserves. | 2003 Jan |
|
| 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
| Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 15 16:58:57 UTC 2023
by
admin
on
Fri Dec 15 16:58:57 UTC 2023
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| Record UNII |
327C7L2BXQ
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| Record Status |
Validated (UNII)
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| Record Version |
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DSLD |
1650 (Number of products:55)
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3109 (Number of products:85)
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JECFA EVALUATION |
PHENETHYLAMINE
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DSLD |
4130 (Number of products:39)
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WIKIPEDIA |
PiHKAL
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18397
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1309741
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m8609
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327C7L2BXQ
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327C7L2BXQ
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DB04325
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64-04-0
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1579
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3526
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C029261
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225237
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10811
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1001
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200-574-4
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PHENETHYLAMINE
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100000126271
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SUB33002
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DTXSID5058773
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SALT/SOLVATE -> PARENT |
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SALT/SOLVATE -> PARENT |
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SALT/SOLVATE -> PARENT |
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SALT/SOLVATE -> PARENT |
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SALT/SOLVATE -> PARENT |
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SALT/SOLVATE -> PARENT |
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DERIVATIVE -> PARENT |
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CONSTITUENT ALWAYS PRESENT -> PARENT |
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ACTIVE MOIETY |
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