Details
Stereochemistry | ACHIRAL |
Molecular Formula | C8H11N.BrH |
Molecular Weight | 202.092 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
Br.NCCC1=CC=CC=C1
InChI
InChIKey=IRAGENYJMTVCCV-UHFFFAOYSA-N
InChI=1S/C8H11N.BrH/c9-7-6-8-4-2-1-3-5-8;/h1-5H,6-7,9H2;1H
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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In vitro melanin binding of NS-49, a phenethylamine class alpha 1A-adrenoceptor agonist. | 2001 |
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Beta-phenylethylamines and the isoquinoline alkaloids. | 2001 Apr |
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Mechanisms of inverse agonism of antipsychotic drugs at the D(2) dopamine receptor: use of a mutant D(2) dopamine receptor that adopts the activated conformation. | 2001 Apr |
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Regulation of human monoamine oxidase B gene by Sp1 and Sp3. | 2001 Apr |
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Effect of the interaction between a low tyramine-producing Lactobacillus and proteolytic staphylococci on biogenic amine production during ripening and storage of dry sausages. | 2001 Apr 11 |
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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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Cloning, sequencing and mutagenesis of the genes for aromatic amine dehydrogenase from Alcaligenes faecalis and evolution of amine dehydrogenases. | 2001 Aug |
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Following the trace of elusive amines. | 2001 Aug 14 |
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Effects of carboxyl-terminal truncations on the activity and solubility of human monoamine oxidase B. | 2001 Aug 3 |
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Amphetamine, 3,4-methylenedioxymethamphetamine, lysergic acid diethylamide, and metabolites of the catecholamine neurotransmitters are agonists of a rat trace amine receptor. | 2001 Dec |
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Trace amines: identification of a family of mammalian G protein-coupled receptors. | 2001 Jul 31 |
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A sensitive method for determining levels of [-]-2,5,-dimethoxy-4-methylamphetamine in the brain tissue. | 2001 Jul-Aug |
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Amino acid-decarboxylase activity of bacteria isolated from fermented pork sausages. | 2001 Jun 15 |
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The phenylacetyl-CoA catabolon: a complex catabolic unit with broad biotechnological applications. | 2001 Mar |
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Growth and metabolic activity of Shewanella putrefaciens maintained under different CO2 and O2 concentrations. | 2001 Mar 20 |
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Molecular mechanism for agonist-promoted alpha(2A)-adrenoceptor activation by norepinephrine and epinephrine. | 2001 May |
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Apical dominance in Pssu-ipt-transformed tobacco. | 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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Subjective and hormonal effects of 3,4-methylenedioxymethamphetamine (MDMA) in humans. | 2002 Aug |
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Content of biogenic amines in a Chardonnay wine obtained through spontaneous and inoculated fermentations. | 2002 Aug 14 |
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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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High-level expression of human liver monoamine oxidase A in Pichia pastoris: comparison with the enzyme expressed in Saccharomyces cerevisiae. | 2002 Feb |
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Enzymatic decarboxylation of tyrosine and phenylalanine to enhance volatility for high-precision isotopic analysis. | 2002 Jan 15 |
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Do we know the mechanism of chiral recognition between cyclodextrins and analytes? | 2002 Jan 15 |
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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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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 |
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Major depressive episodes and diet pills. | 2002 Oct |
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Plausible molecular mechanism for activation by fumarate and electron transfer of the dopamine beta-mono-oxygenase reaction. | 2002 Oct 1 |
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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
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