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Details

Stereochemistry ACHIRAL
Molecular Formula C8H11N.C6H8O7
Molecular Weight 313.3032
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of PHENETHYLAMINE CITRATE

SMILES

NCCC1=CC=CC=C1.OC(=O)CC(O)(CC(O)=O)C(O)=O

InChI

InChIKey=CTBJILANYAWODF-UHFFFAOYSA-N
InChI=1S/C8H11N.C6H8O7/c9-7-6-8-4-2-1-3-5-8;7-3(8)1-6(13,5(11)12)2-4(9)10/h1-5H,6-7,9H2;13H,1-2H2,(H,7,8)(H,9,10)(H,11,12)

HIDE SMILES / InChI

Molecular Formula C6H8O7
Molecular Weight 192.1235
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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.

Originator

Sources: Nencki M. Festchrift für 40 jähriges Jubiläum des Prof Valentin. Bern: 1876.
Curator's Comment: reference retrieved from https://www.ncbi.nlm.nih.gov/pubmed/17888514

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
0.3 µM [EC50]
Target ID: Q9P1P5
Gene ID: 9287.0
Gene Symbol: TAAR2
Target Organism: Homo sapiens (Human)
0.43 nM [EC50]
Conditions
PubMed

PubMed

TitleDatePubMed
Beta-phenylethylamines and the isoquinoline alkaloids.
2001 Apr
Regulation of human monoamine oxidase B gene by Sp1 and Sp3.
2001 Apr
beta-Phenylethylamine modulates acetylcholine release in the rat striatum: involvement of a dopamine D(2) receptor mechanism.
2001 Apr 20
Spectroscopic observation of intermediates formed during the oxidative half-reaction of copper/topa quinone-containing phenylethylamine oxidase.
2001 Dec 25
Use of beta-cyclodextrin in the capillary zone electrophoretic separation of the components of clandestine heroin preparations.
2001 Jul 27
A molecular approach to the study of structure-activity correlation for some amphetamines.
2001 Jul-Sep
Involvement of adrenal medulla grafts in the open field behavior.
2001 Jun
Baclofen treatment in Tourette syndrome: a double-blind, placebo-controlled, crossover trial.
2001 Mar 13
Monoamine oxidase in developing rat renal cortex: effect of dexamethasone treatment.
2001 Mar 9
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
Platelet monoamine oxidase in healthy 9- and 15-years old children: the effect of gender, smoking and puberty.
2001 Nov
Oxidation of phenethylamine derivatives by cytochrome P450 2D6: the issue of substrate protonation in binding and catalysis.
2001 Nov 27
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
Oxygen dependency of monoamine oxidase activity in the intact lung.
2001 Oct
Conserved tyrosine-369 in the active site of Escherichia coli copper amine oxidase is not essential.
2001 Oct 30
Postmortem tissue concentrations of venlafaxine.
2001 Sep 15
Probing the catalytic mechanism of Escherichia coli amine oxidase using mutational variants and a reversible inhibitor as a substrate analogue.
2002 Aug 1
[Localization of non-monoaminergic aromatic L-amino acid decarboxylase neurons (D-neurons) in the human striatum and their functional significance].
2002 Dec
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
Analysis of conserved active site residues in monoamine oxidase A and B and their three-dimensional molecular modeling.
2002 May 10
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
Serotonin 5-hydroxytryptamine 2A receptor-coupled phospholipase C and phospholipase A2 signaling pathways have different receptor reserves.
2003 Jan
Patents

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
1 uM phenethylamine alters monoamine transporter function in vitro
Substance Class Chemical
Created
by admin
on Sat Dec 16 18:41:58 UTC 2023
Edited
by admin
on Sat Dec 16 18:41:58 UTC 2023
Record UNII
235L88TMD3
Record Status Validated (UNII)
Record Version
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Name Type Language
PHENETHYLAMINE CITRATE
Common Name English
BENZENEETHANAMINE, 2-HYDROXY-1,2,3-PROPANETRICARBOXYLATE (1:1)
Systematic Name English
Code System Code Type Description
SMS_ID
100000090347
Created by admin on Sat Dec 16 18:41:58 UTC 2023 , Edited by admin on Sat Dec 16 18:41:58 UTC 2023
PRIMARY
FDA UNII
235L88TMD3
Created by admin on Sat Dec 16 18:41:58 UTC 2023 , Edited by admin on Sat Dec 16 18:41:58 UTC 2023
PRIMARY
CAS
84473-65-4
Created by admin on Sat Dec 16 18:41:58 UTC 2023 , Edited by admin on Sat Dec 16 18:41:58 UTC 2023
PRIMARY
PUBCHEM
57354249
Created by admin on Sat Dec 16 18:41:58 UTC 2023 , Edited by admin on Sat Dec 16 18:41:58 UTC 2023
PRIMARY
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