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

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

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 75 Target ID: CHEMBL2039 Sources: https://www.ncbi.nlm.nih.gov/pubmed/7205271	Substrate 661
Trace amine-associated receptor 1 48 Target ID: CHEMBL5857 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27424325 \| https://www.ncbi.nlm.nih.gov/pubmed/18182557	Activator 1447	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 1447	0.43 nM [EC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Depression 240 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
Role of copper ion in bacterial copper amine oxidase: spectroscopic and crystallographic studies of metal-substituted enzymes.	2003-01-29	12537504
Serotonin 5-hydroxytryptamine 2A receptor-coupled phospholipase C and phospholipase A2 signaling pathways have different receptor reserves.	2003-01	12490596
Degradation of benzyldimethylalkylammonium chloride by Aeromonas hydrophila sp. K.	2003	12534818
Analysis of enantiomers of chiral phenethylamine drugs by capillary gas chromatography/mass spectrometry/flame-ionization detection and pre-column chiral derivatization.	2002-12-31	12543494
[Localization of non-monoaminergic aromatic L-amino acid decarboxylase neurons (D-neurons) in the human striatum and their functional significance].	2002-12	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.	2002-12	12413828
The effects of acute and subchronic treatment with fluoxetine and citalopram on stimulus control by DOM.	2002-12	12376156
Novel dual inhibitors of AChE and MAO derived from hydroxy aminoindan and phenethylamine as potential treatment for Alzheimer's disease.	2002-11-21	12431053
[Tetrahydroisoquinoline derivatives as possible Parkinson's disease-inducing substances].	2002-11	12440154
Plausible molecular mechanism for activation by fumarate and electron transfer of the dopamine beta-mono-oxygenase reaction.	2002-10-01	12038965
Production of amines in equine cecal contents in an in vitro model of carbohydrate overload.	2002-10	12413088
Major depressive episodes and diet pills.	2002-10	12387686
Stimulation of the catecholaminergic and serotoninergic neurons in the rat brain by R-(-)-1-(benzofuran-2-yl)-2-propylaminopentane, (-)-BPAP.	2002-09-20	12204771
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.	2002-09-13	12175892
Formation of biogenic amines in a typical semihard Italian cheese.	2002-09	12233866
Increased urine phenylethylamine after methylphenidate treatment in children with ADHD.	2002-09	12205654
High-performance liquid chromatographic determination of biogenic amines in poultry carcasses.	2002-08-28	12188600
Content of biogenic amines in a Chardonnay wine obtained through spontaneous and inoculated fermentations.	2002-08-14	12166978
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.	2002-08-09	12166811
A sensitive method for determining levels of [-]-2,5,-dimethoxy-4-methylamphetamine in the brain tissue.	2002-08-08	12164258
Probing the catalytic mechanism of Escherichia coli amine oxidase using mutational variants and a reversible inhibitor as a substrate analogue.	2002-08-01	11985492
[Human striatal D-neurons and their significance].	2002-08	12373866
Subjective and hormonal effects of 3,4-methylenedioxymethamphetamine (MDMA) in humans.	2002-08	12172693
Characterization of selected Spanish table wine samples according to their biogenic amine content from liquid chromatographic determination.	2002-07-31	12137502
Monoamine-dependent production of reactive oxygen species catalyzed by pseudoperoxidase activity of human hemoglobin.	2002-06	12162542
Application of ligand SAR, receptor modeling and receptor mutagenesis to the discovery and development of a new class of 5-HT(2A) ligands.	2002-06	12052195
Monoamine oxidase A and B activities in embryonic chick hepatocytes: differential regulation by retinoic acid.	2002-06	11979502
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.	2002-05-17	12108645
Analysis of conserved active site residues in monoamine oxidase A and B and their three-dimensional molecular modeling.	2002-05-10	11861643
Phenylethylamine induces an increase in cytosolic Ca2+ in yeast.	2002-05	12092817
[Decreased beta-phenylethylamine in urine of children with attention deficit hyperactivity disorder and autistic disorder].	2002-05	12030014
[Neuroimaging and neurochemical studies of Rett syndrome].	2002-05	12030008
Heart rate dynamics in monoamine oxidase-A- and -B-deficient mice.	2002-05	11959640
Intercalated organic-inorganic perovskites stabilized by fluoroaryl-aryl interactions.	2002-04-22	11952366
Geometry-affinity relationships of the selective serotonin receptor ligand 9-(aminomethyl)-9,10-dihydroanthracene.	2002-04-11	11931619
An MCASE approach to the search of a cure for Parkinson's Disease.	2002-04-02	11926966
Cp*(2)TiMe(2): an improved catalyst for the intermolecular addition of n-alkyl- and benzylamines to alkynes.	2002-03-22	11895418
Inhibition of copper amine oxidases by pyridine-derived aldoximes and ketoximes.	2002-03-07	11879727
Rat striatal monoamine oxidase-B inhibition by l-deprenyl and rasagiline: its relationship to 2-phenylethylamine-induced stereotypy and Parkinson's disease.	2002-03	12039419
Spectroscopic evidence in support of horseradish peroxidase compound II-catalyzed oxidation of salicylic acid but not of phenylethylamine.	2002-03	12005064
Increased baroreceptor response in mice deficient in monoamine oxidase A and B.	2002-03	11834493
Stereospecific cleavage of carbon-phosphorus bonds: stereochemical course of the phosphinoyl curtius (Harger) reaction.	2002-02-09	11835571
High-level expression of human liver monoamine oxidase A in Pichia pastoris: comparison with the enzyme expressed in Saccharomyces cerevisiae.	2002-02	11812236
A TLC visualisation reagent for dimethylamphetamine and other abused tertiary amines.	2002-01-17	11793881
Enzymatic decarboxylation of tyrosine and phenylalanine to enhance volatility for high-precision isotopic analysis.	2002-01-15	11817371
Do we know the mechanism of chiral recognition between cyclodextrins and analytes?	2002-01-15	11755754
Automated headspace solid-phase microextraction and in-matrix derivatization for the determination of amphetamine-related drugs in human urine by gas chromatography-mass spectrometry.	2002-01	11866382
The enigma of conditioned taste aversion learning: stimulus properties of 2-phenylethylamine derivatives.	2002	12479782
Psychomotor stimulant effects of beta-phenylethylamine in monkeys treated with MAO-B inhibitors.	2001-12	11797065
Phenibut (beta-phenyl-GABA): a tranquilizer and nootropic drug.	2001	11830761

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

Substance Class	Chemical Created by `admin` on `Mon Mar 31 18:38:47 GMT 2025` Edited by `admin` on `Mon Mar 31 18:38:47 GMT 2025`
Record UNII	327C7L2BXQ
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

2-PHENYLETHYLAMINE

Preferred Name

English

PHENETHYLAMINE

Systematic Name

English

PHENETHYLAMINE [MI]

Common Name

English

2-Phenethylamine

Common Name

English

2-PHENYLETHYLAMINE [HSDB]

Common 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)