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Phenethylamine, or β-phenylethylamine or 2-phenylethylamine, is an alkaloid and monoamine. Phenethylamine also has a constitutional isomer α-phenylethylamine (1-phenylethylamine), which has two stereoisomers: (R)-(+)-1-phenylethylamine and (S)-(-)-1-phenylethylamine. In the human brain, 2-phenethylamine is believed to function as a neuromodulator or neurotransmitter (trace amine). Phenethylamine is a natural compound biosynthesized from the amino acid phenylalanine by enzymatic decarboxylation. It is also found in many foods such as chocolate, especially after microbial fermentation. However trace amounts from food is quickly metabolized by the enzyme MAO-B, preventing significant concentrations from reaching the brain.[2][3]
Phenylethylamine is a precursor to the neurotransmitter phenylethanolamine.[4]
D-Phenylalanine increases the brain content of phenylethylamine .[5] Phenylethylamine has been shown at least indirectly to satisfy the four main criteria required to demonstrate that a neuroamine sustains mood and that its deficit can be responsible for depression.[5] while at the same time inhibiting DA neuron firings.[6][7] It also modulates noradrenergic transmission.[8] Phenethylamine, along with tyramine, reversibly depresses the slow GABAB receptor inhibitory post-synaptic potential in midbrain dopaminergic cells.[9]
Low levels are found in those suffering from attention deficit disorder[10] and often in depression, while levels are elevated in schizophrenia.[11] This is associated with low dopamine in ADHD and depression and high dopamine in schizophrenia.