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
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)
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.
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL2039 Sources: https://www.ncbi.nlm.nih.gov/pubmed/7205271 |
|||
Target ID: CHEMBL5857 |
0.3 µM [EC50] | ||
Target ID: Q9P1P5 Gene ID: 9287.0 Gene Symbol: TAAR2 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/27424325 |
0.43 nM [EC50] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | Unknown Approved UseUnknown |
PubMed
Title | Date | PubMed |
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Beta-phenylethylamines and the isoquinoline alkaloids. | 2001 Apr |
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Regulation of human monoamine oxidase B gene by Sp1 and Sp3. | 2001 Apr |
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beta-Phenylethylamine modulates acetylcholine release in the rat striatum: involvement of a dopamine D(2) receptor mechanism. | 2001 Apr 20 |
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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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Use of beta-cyclodextrin in the capillary zone electrophoretic separation of the components of clandestine heroin preparations. | 2001 Jul 27 |
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A molecular approach to the study of structure-activity correlation for some amphetamines. | 2001 Jul-Sep |
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Involvement of adrenal medulla grafts in the open field behavior. | 2001 Jun |
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Baclofen treatment in Tourette syndrome: a double-blind, placebo-controlled, crossover trial. | 2001 Mar 13 |
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Monoamine oxidase in developing rat renal cortex: effect of dexamethasone treatment. | 2001 Mar 9 |
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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 |
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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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Oxidation of phenethylamine derivatives by cytochrome P450 2D6: the issue of substrate protonation in binding and catalysis. | 2001 Nov 27 |
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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 |
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Oxygen dependency of monoamine oxidase activity in the intact lung. | 2001 Oct |
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Conserved tyrosine-369 in the active site of Escherichia coli copper amine oxidase is not essential. | 2001 Oct 30 |
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Postmortem tissue concentrations of venlafaxine. | 2001 Sep 15 |
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Probing the catalytic mechanism of Escherichia coli amine oxidase using mutational variants and a reversible inhibitor as a substrate analogue. | 2002 Aug 1 |
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[Localization of non-monoaminergic aromatic L-amino acid decarboxylase neurons (D-neurons) in the human striatum and their functional significance]. | 2002 Dec |
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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 |
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Analysis of conserved active site residues in monoamine oxidase A and B and their three-dimensional molecular modeling. | 2002 May 10 |
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Novel dual inhibitors of AChE and MAO derived from hydroxy aminoindan and phenethylamine as potential treatment for Alzheimer's disease. | 2002 Nov 21 |
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Production of amines in equine cecal contents in an in vitro model of carbohydrate overload. | 2002 Oct |
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Major depressive episodes and diet pills. | 2002 Oct |
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Serotonin 5-hydroxytryptamine 2A receptor-coupled phospholipase C and phospholipase A2 signaling pathways have different receptor reserves. | 2003 Jan |
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
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/18182557
1 uM phenethylamine alters monoamine transporter function in vitro
Substance Class |
Chemical
Created
by
admin
on
Edited
Sat Dec 16 18:41:58 UTC 2023
by
admin
on
Sat Dec 16 18:41:58 UTC 2023
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Record UNII |
235L88TMD3
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Record Status |
Validated (UNII)
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Record Version |
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