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Phenethylamine

Phenethylamine
Image of the phenethylamine skeleton
Ball-and-stick model of phenethylamine
Clinical data
Pronunciation /fɛnˈɛθələmn/
Dependence
liability
Psychological: low–moderate
Physical: none
Addiction
liability
Low (without an MAO-B inhibitor)
Moderate (with an MAO-B inhibitor)
Routes of
administration
Oral
ATC code none
Legal status
Legal status
  • AU: Unscheduled
  • CA: Unscheduled
  • UK: Unscheduled
  • US: Unscheduled
  • UN: Unscheduled
Pharmacokinetic data
Metabolism Primarily: MAO-B and ALDH
Other enzymes: MAO-A, SSAOs, PNMT, AANAT, FMO3, and others
Biological half-life Exogenous: 5–10 minutes
Endogenous: ~30 seconds
Identifiers
Synonyms 1-amino-2-phenylethane
CAS Number 64-04-0 YesY
PubChem (CID) 1001
IUPHAR/BPS 2144
DrugBank DB04325 YesY
ChemSpider 13856352 YesY
UNII 327C7L2BXQ YesY
KEGG C05332 YesY
ChEBI CHEBI:18397 YesY
ChEMBL CHEMBL610 YesY
NIAID ChemDB 018561
ECHA InfoCard 100.000.523
Chemical and physical data
Formula C8H11N
Molar mass 121.18 g/mol
3D model (Jmol) Interactive image
Density 0.9640 g/cm3
Melting point −60 °C (−76 °F)
Boiling point 195 °C (383 °F)
  

Phenethylamine (PEA), also known as β-phenylethylamine (β-PEA) and 2-phenylethan-1-amine, is an organic compound and a natural monoamine alkaloid, a trace amine, and also the name of a class of chemicals with many members that are well known for their psychoactive and stimulant effects.

Phenylethylamine functions as a monoaminergic neuromodulator and, to a lesser extent, a neurotransmitter in the human central nervous system. It is biosynthesized from the amino acid L-phenylalanine by enzymatic decarboxylation via the enzyme aromatic L-amino acid decarboxylase. In addition to its presence in 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 primarily metabolized in the small intestine by monoamine oxidase B (MAO-B) and then aldehyde dehydrogenase (ALDH), which convert it to phenylacetic acid. This prevents significant concentrations from reaching the brain when taken in low doses.


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Wikipedia

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