Phenethylamine

Phenethylamine (PEA) is an organic compound, natural monoamine alkaloid, and trace amine, which acts as a central nervous system stimulant in humans. In the brain, phenethylamine regulates monoamine neurotransmission by binding to trace amine-associated receptor 1 (TAAR1) and inhibiting vesicular monoamine transporter 2 (VMAT2) in monoamine neurons. To a lesser extent, it also acts as a neurotransmitter in the human central nervous system. In mammals, phenethylamine is produced from the amino acid L-phenylalanine by the enzyme aromatic L-amino acid decarboxylase via enzymatic decarboxylation. In addition to its presence in mammals, phenethylamine is found in many other organisms and foods, such as chocolate, especially after microbial fermentation.

Phenethylamine
Clinical data
Pronunciation/fɛnˈɛθələmn/
Other namesPEA; phenylethylamine, phetamine
Dependence
liability
Psychological: low–moderate
Physical: none
Addiction
liability
None–Low (w/o an MAO-B inhibitor)
Moderate (with an MAO-B inhibitor)
Routes of
administration
Oral (taken by mouth)
Drug classCNSTooltip central nervous system stimulant, anorectic
ATC code
  • none
Physiological data
Source tissuesSubstantia nigra pars compacta;
Ventral tegmental area;
Locus coeruleus;
many others
Target tissuesSystem-wide
ReceptorsVaries greatly across species;
Human receptors: hTAAR1
PrecursorL-Phenylalanine
BiosynthesisAromatic L-amino acid decarboxylase (AADC)
MetabolismPrimarily: MAO-B
Other enzymes: MAO-A, SSAOs (AOC2 & AOC3), PNMT, AANAT, FMO3, and others
Legal status
Legal status
  • AU: Unscheduled
  • CA: Unscheduled
  • NZ: Unscheduled
  • UK: Unscheduled
  • US: Unscheduled
  • UN: Unscheduled
Pharmacokinetic data
MetabolismPrimarily: MAO-B
Other enzymes: MAO-A, SSAOs (AOC2 & AOC3), PNMT, AANAT, FMO3, and others
Elimination half-life
  • Exogenous: 5–10 minutes
  • Endogenous: ~30 seconds
ExcretionRenal (kidneys)
Identifiers
  • 2-Phenylethan-1-amine
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
NIAID ChemDB
CompTox Dashboard (EPA)
ECHA InfoCard100.000.523
Chemical and physical data
FormulaC8H11N
Molar mass121.183 g·mol−1
3D model (JSmol)
Density0.9640 g/cm3
Melting point−60 °C (−76 °F)
Boiling point195 °C (383 °F)
  • NCCc1ccccc1
  • InChI=1S/C8H11N/c9-7-6-8-4-2-1-3-5-8/h1-5H,6-7,9H2 Y
  • Key:BHHGXPLMPWCGHP-UHFFFAOYSA-N Y
  (verify)

Phenethylamine is sold as a dietary supplement for purported mood and weight loss-related therapeutic benefits; however, in orally ingested phenethylamine, a significant amount is metabolized in the small intestine by monoamine oxidase B (MAO-B) and then aldehyde dehydrogenase (ALDH), which converts it to phenylacetic acid. This means that for significant concentrations to reach the brain, the dosage must be higher than for other methods of administration. Some authors postulated its role in people's falling-in-love without substantiating it with any direct evidence.

Phenethylamines, or more properly, substituted phenethylamines, are the group of phenethylamine derivatives that contain phenethylamine as a "backbone"; in other words, this chemical class includes derivative compounds that are formed by replacing one or more hydrogen atoms in the phenethylamine core structure with substituents. The class of substituted phenethylamines includes all substituted amphetamines, and substituted methylenedioxyphenethylamines (MDxx), and contains many drugs which act as empathogens, stimulants, psychedelics, anorectics, bronchodilators, decongestants, and/or antidepressants, among others.

This article is issued from Wikipedia. The text is licensed under Creative Commons - Attribution - Sharealike. Additional terms may apply for the media files.