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 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
Tissue distribution of NS-49, a phenethylamine class alpha 1A-adrenoceptor agonist, in pigmented rats.	2001	11413741
Pharmacokinetics of NS-49, a phenethylamine class alpha 1A-adrenoceptor agonist. 4th communication: tissue distribution, placental transfer and milk secretion of radioactivity in rats after a single oral administration of 14C-NS-49, and effects of repeated administration on its pharmacokinetics.	2001	11413740
beta-Phenylethylamine modulates acetylcholine release in the rat striatum: involvement of a dopamine D(2) receptor mechanism.	2001 Apr 20	11334866
Effects of carboxyl-terminal truncations on the activity and solubility of human monoamine oxidase B.	2001 Aug 3	11371556
S(+)-4-(1-Phenylethylamino)quinazolines as inhibitors of human immunoglobulin E synthesis: potency is dictated by stereochemistry and atomic point charges at N-1.	2001 Aug 30	11520212
Psychomotor stimulant effects of beta-phenylethylamine in monkeys treated with MAO-B inhibitors.	2001 Dec	11797065
Amphetamine, 3,4-methylenedioxymethamphetamine, lysergic acid diethylamide, and metabolites of the catecholamine neurotransmitters are agonists of a rat trace amine receptor.	2001 Dec	11723224
Apomorphine, dopamine and phenylethylamine reduce the proportion of phosphorylated insulin receptor substrate 1.	2001 Dec 14	11755133
New observations on the secondary chemistry of world Ephedra (Ephedraceae).	2001 Jul	11454619
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
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
Molecular mechanism for agonist-promoted alpha(2A)-adrenoceptor activation by norepinephrine and epinephrine.	2001 May	11306720
I1 receptors, cardiovascular function, and metabolism.	2001 Nov	11721890
Hydrogen-deuterium exchange at non-labile sites: a new reaction facet with broad implications for structural and dynamic determinations.	2001 Nov	11720390
Biochemical, behavioral, physiologic, and neurodevelopmental changes in mice deficient in monoamine oxidase A or B.	2001 Nov 15	11750790
Oxidation of phenethylamine derivatives by cytochrome P450 2D6: the issue of substrate protonation in binding and catalysis.	2001 Nov 27	11714275
Inhibition of copper amine oxidases by pyridine-derived aldoximes and ketoximes.	2001 Nov-Dec	11879727
Phenylethylamine, a possible link to the antidepressant effects of exercise?	2001 Oct	11579070
A TLC visualisation reagent for dimethylamphetamine and other abused tertiary amines.	2001 Oct-Dec	11793881
Postmortem tissue concentrations of venlafaxine.	2001 Sep 15	11516890
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
Geometry-affinity relationships of the selective serotonin receptor ligand 9-(aminomethyl)-9,10-dihydroanthracene.	2002 Apr 11	11931619
An MCASE approach to the search of a cure for Parkinson's Disease.	2002 Apr 2	11926966
Intercalated organic-inorganic perovskites stabilized by fluoroaryl-aryl interactions.	2002 Apr 22	11952366
Probing the catalytic mechanism of Escherichia coli amine oxidase using mutational variants and a reversible inhibitor as a substrate analogue.	2002 Aug 1	11985492
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
High-level expression of human liver monoamine oxidase A in Pichia pastoris: comparison with the enzyme expressed in Saccharomyces cerevisiae.	2002 Feb	11812236
Stereospecific cleavage of carbon-phosphorus bonds: stereochemical course of the phosphinoyl curtius (Harger) reaction.	2002 Feb-Mar	11835571
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	11866382
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
Monoamine oxidase A and B activities in embryonic chick hepatocytes: differential regulation by retinoic acid.	2002 Jun	11979502
Rat striatal monoamine oxidase-B inhibition by l-deprenyl and rasagiline: its relationship to 2-phenylethylamine-induced stereotypy and Parkinson's disease.	2002 Mar	12039419
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
Cp*(2)TiMe(2): an improved catalyst for the intermolecular addition of n-alkyl- and benzylamines to alkynes.	2002 Mar 22	11895418
[Decreased beta-phenylethylamine in urine of children with attention deficit hyperactivity disorder and autistic disorder].	2002 May	12030014
[Neuroimaging and neurochemical studies of Rett syndrome].	2002 May	12030008
Heart rate dynamics in monoamine oxidase-A- and -B-deficient mice.	2002 May	11959640
Analysis of conserved active site residues in monoamine oxidase A and B and their three-dimensional molecular modeling.	2002 May 10	11861643
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	12108645
Production of amines in equine cecal contents in an in vitro model of carbohydrate overload.	2002 Oct	12413088
Plausible molecular mechanism for activation by fumarate and electron transfer of the dopamine beta-mono-oxygenase reaction.	2002 Oct 1	12038965
Formation of biogenic amines in a typical semihard Italian cheese.	2002 Sep	12233866
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

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 `Fri Dec 15 16:58:57 GMT 2023` Edited by `admin` on `Fri Dec 15 16:58:57 GMT 2023`
Record UNII	327C7L2BXQ
Record Status	`Validated (UNII)`
Record Version

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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)