Phenethylamine
From Wikipedia, the free encyclopedia
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| Systematic (IUPAC) name | |
| phenylethan-2-amine | |
| Identifiers | |
| CAS number | 64-04-0 |
| ATC code | ? |
| PubChem | CID 1001 |
| ChemSpider | 13856352 |
| Chemical data | |
| Formula | C8H11N |
| Mol. mass | 121.18 g/mol |
| SMILES | eMolecules & PubChem |
| Synonyms | 2-phenylethylamine, β-phenylethylamine, 1-amino-2-phenylethane |
| Pharmacokinetic data | |
| Metabolism | MAO-A, MAO-B, ALDH, DBH, CYP2D6 |
| Half-life | ~5-10 minutes |
| Therapeutic considerations | |
| Pregnancy cat. | ? |
| Legal status | Uncontrolled |
| Routes | Oral |
Phenethylamine (PEA) is a natural monoamine alkaloid, trace amine, and psychoactive drug with stimulantmammalian central nervous system, phenethylamine is believed to function as a neuromodulatorneurotransmitter. It is biosynthesized from the amino acid phenylalanine by enzymatic decarboxylation. Besides mammals, phenethylamine is found in many other organisms and foods such as chocolate, especially after microbial fermentation. It is sold as a dietary supplement for purported mood and weight loss-related therapeutic benefits; however, orally ingested phenethylamine is usually inactive on account of extensive first-pass metabolism by monoamine oxidase (MAO) into phenylacetic acid, preventing significant concentrations from reaching the brain.[1][2] effects. In the or
The group of phenethylamine derivatives is referred to as the phenethylamines. Substituted phenethylamines, substituted amphetamines, and substituted methylenedioxyphenethylamines (MDxx) are a series of broad and diverse classes of compounds derived from phenethylamine that include stimulants, psychedelics, and entactogens, as well as anorectics, bronchodilators, decongestants, and antidepressants, among others.
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[edit] Chemistry
Phenethylamine is an amine, consisting of a benzene ring and an aminoethyl group. It is a colorless liquid at room temperature. Phenethylamine is soluble in water, ethanol, and ether. Similar to other low-molecular-weight amines, it has a fishy odor. Upon exposure to air, it forms a solid carbonate salt with carbon dioxide. Phenethylamine is strongly basic and forms a stable crystalline hydrochloride salt with a melting point of 217 °C. Phenethylamine is also a skin irritant and possible sensitizer.
Phenethylamine has an inactive constitutional isomer 1-phenylethylamine, which itself has two stereoisomers: (R)-(+)-1-phenylethylamine and (S)-(-)-1-phenylethylamine.
[edit] Pharmacology
Phenethylamine, similarly to amphetamine, acts as a releasing agent of norepinephrine and dopamine.[3][4][5][6] For this reason, it has been called the "body's endogenous amphetamine". However when taken orally it is rapidly metabolized.
Low concentrations of endogenous phenethylamine are found in those suffering from attention-deficit hyperactivity disorder (ADHD)[7] and often in clinical depression, while levels are elevated in schizophrenia.[8]
