PHENETHYLAMINE

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

Structure Search

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

HIDE SMILES / InChI

Description
Sources: https://examine.com/supplements/phenylethylamine/ | https://www.ncbi.nlm.nih.gov/pubmed/15228583 | https://www.ncbi.nlm.nih.gov/pubmed/7205271 | https://www.ncbi.nlm.nih.gov/pubmed/27424325 | https://www.ncbi.nlm.nih.gov/pubmed/18182557 | https://www.ncbi.nlm.nih.gov/pubmed/23494844 | https://www.ncbi.nlm.nih.gov/pubmed/7711493

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.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Potency
Monoamine oxidase B 72 Target ID: CHEMBL2039 Sources: https://www.ncbi.nlm.nih.gov/pubmed/7205271	Substrate 661
Trace amine-associated receptor 1 47 Target ID: CHEMBL5857 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27424325 \| https://www.ncbi.nlm.nih.gov/pubmed/18182557	Activator 1430	0.3 µM [EC50]
Trace amine-associated receptor 2 10 Target ID: Q9P1P5 Gene ID: 9287.0 Gene Symbol: TAAR2 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/27424325	Activator 1430	0.43 nM [EC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Depression 235 Sources: https://www.ncbi.nlm.nih.gov/pubmed/7711493 https://www.webmd.com/vitamins-supplements/ingredientmono-1274-phenethylamine.aspx?activeingredientid=1274&activeingredientname=phenethylamine	Primary		Natural Metabolite	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
In vitro melanin binding of NS-49, a phenethylamine class alpha 1A-adrenoceptor agonist.	2001	11367870
Following the trace of elusive amines.	2001 Aug 14	11504935
Effects of carboxyl-terminal truncations on the activity and solubility of human monoamine oxidase B.	2001 Aug 3	11371556
Neurobiology and neurochemistry of Rett syndrome.	2001 Dec	11738843
Amphetamine, 3,4-methylenedioxymethamphetamine, lysergic acid diethylamide, and metabolites of the catecholamine neurotransmitters are agonists of a rat trace amine receptor.	2001 Dec	11723224
Poly(amidoamine)s as potential nonviral vectors: ability to form interpolyelectrolyte complexes and to mediate transfection in vitro.	2001 Fall	11710005
Use of beta-cyclodextrin in the capillary zone electrophoretic separation of the components of clandestine heroin preparations.	2001 Jul 27	11521902
A sensitive method for determining levels of [-]-2,5,-dimethoxy-4-methylamphetamine in the brain tissue.	2001 Jul-Aug	12164258
Evolution of microbial populations and biogenic amine production in dry sausages produced in Southern Italy.	2001 Jun	11412318
Amino acid-decarboxylase activity of bacteria isolated from fermented pork sausages.	2001 Jun 15	11428577
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	11377178
Hydrogen-deuterium exchange at non-labile sites: a new reaction facet with broad implications for structural and dynamic determinations.	2001 Nov	11720390
Apical dominance in Pssu-ipt-transformed tobacco.	2001 Nov	11684189
Fluorometric determination of DL-fenfluramine, DL-norfenfluramine and phentermine in plasma by achiral and chiral high-performance liquid chromatography.	2001 Nov 5	11710586
Inhibition of copper amine oxidases by pyridine-derived aldoximes and ketoximes.	2001 Nov-Dec	11879727
High performance liquid chromatography with UV detection for the simultaneous determination of sympathomimetic amines using 4-(4,5-diphenyl-1H-imidazole-2-yl)benzoyl chloride as a label.	2001 Oct	11559922
Oxygen dependency of monoamine oxidase activity in the intact lung.	2001 Oct	11557601
A TLC visualisation reagent for dimethylamphetamine and other abused tertiary amines.	2001 Oct-Dec	11793881
Synthesis and biological data of 4-amino-1-(2-chloro-2-phenylethyl)-1H-pyrazolo[3,4-b]pyridine-5-carboxylic acid ethyl esters, a new series of A1-adenosine receptor (A1AR) ligands.	2001 Sep 17	11549462
Phenibut (beta-phenyl-GABA): a tranquilizer and nootropic drug.	2001 Winter	11830761
The enigma of conditioned taste aversion learning: stimulus properties of 2-phenylethylamine derivatives.	2002	12479782
Geometry-affinity relationships of the selective serotonin receptor ligand 9-(aminomethyl)-9,10-dihydroanthracene.	2002 Apr 11	11931619
[Human striatal D-neurons and their significance].	2002 Aug	12373866
Subjective and hormonal effects of 3,4-methylenedioxymethamphetamine (MDMA) in humans.	2002 Aug	12172693
Content of biogenic amines in a Chardonnay wine obtained through spontaneous and inoculated fermentations.	2002 Aug 14	12166978
High-performance liquid chromatographic determination of biogenic amines in poultry carcasses.	2002 Aug 28	12188600
[Localization of non-monoaminergic aromatic L-amino acid decarboxylase neurons (D-neurons) in the human striatum and their functional significance].	2002 Dec	12557414
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	12413828
The effects of acute and subchronic treatment with fluoxetine and citalopram on stimulus control by DOM.	2002 Dec	12376156
Analysis of enantiomers of chiral phenethylamine drugs by capillary gas chromatography/mass spectrometry/flame-ionization detection and pre-column chiral derivatization.	2002 Dec 31	12543494
Stereospecific cleavage of carbon-phosphorus bonds: stereochemical course of the phosphinoyl curtius (Harger) reaction.	2002 Feb-Mar	11835571
Enzymatic decarboxylation of tyrosine and phenylalanine to enhance volatility for high-precision isotopic analysis.	2002 Jan 15	11817371
Do we know the mechanism of chiral recognition between cyclodextrins and analytes?	2002 Jan 15	11755754
Rapid simultaneous determination of amphetamine, methamphetamine, 3,4-methylenedioxyamphetamine, 3,4-methylenedioxymethamphetamine, and 3,4-methylenedioxyethylamphetamine in urine by solid-phase extraction and GC-MS: a method optimized for high-volume laboratories.	2002 Jul-Aug	12166811
Monoamine-dependent production of reactive oxygen species catalyzed by pseudoperoxidase activity of human hemoglobin.	2002 Jun	12162542
Spectroscopic evidence in support of horseradish peroxidase compound II-catalyzed oxidation of salicylic acid but not of phenylethylamine.	2002 Mar	12005064
Increased baroreceptor response in mice deficient in monoamine oxidase A and B.	2002 Mar	11834493
Phenylethylamine induces an increase in cytosolic Ca2+ in yeast.	2002 May	12092817
[Neuroimaging and neurochemical studies of Rett syndrome].	2002 May	12030008
[Tetrahydroisoquinoline derivatives as possible Parkinson's disease-inducing substances].	2002 Nov	12440154
Novel dual inhibitors of AChE and MAO derived from hydroxy aminoindan and phenethylamine as potential treatment for Alzheimer's disease.	2002 Nov 21	12431053
Production of amines in equine cecal contents in an in vitro model of carbohydrate overload.	2002 Oct	12413088
Major depressive episodes and diet pills.	2002 Oct	12387686
Formation of biogenic amines in a typical semihard Italian cheese.	2002 Sep	12233866
Increased urine phenylethylamine after methylphenidate treatment in children with ADHD.	2002 Sep	12205654
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	12175892
Stimulation of the catecholaminergic and serotoninergic neurons in the rat brain by R-(-)-1-(benzofuran-2-yl)-2-propylaminopentane, (-)-BPAP.	2002 Sep 20	12204771
Degradation of benzyldimethylalkylammonium chloride by Aeromonas hydrophila sp. K.	2003	12534818
Serotonin 5-hydroxytryptamine 2A receptor-coupled phospholipase C and phospholipase A2 signaling pathways have different receptor reserves.	2003 Jan	12490596
Role of copper ion in bacterial copper amine oxidase: spectroscopic and crystallographic studies of metal-substituted enzymes.	2003 Jan 29	12537504

Patents

Sample Use Guides

In Vivo Use Guide

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

1 uM phenethylamine alters monoamine transporter function in vitro

Name

Type

Language

PHENETHYLAMINE

Systematic Name

English

PHENETHYLAMINE [MI]

Common Name

English

2-Phenethylamine

Common Name

English

2-PHENYLETHYLAMINE [HSDB]

Common Name

English

2-PHENYLETHYLAMINE

Systematic Name

English

.BETA.-PHENYLETHYLAMINE

Systematic Name

English

PHENETHYLAMINE [FHFI]

Common Name

English

Phenethylamine [WHO-DD]

Common Name

English

NSC-10811

Code

English

FEMA NO. 3220

Code

English

Classification Tree Code System Code

DSLD

1650 (Number of products:55)