Phenethylamine

Phenethylamine
Clinical data


Pronunciation	/fɛnˈɛθələmiːn/
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
IUPAC name 2-Phenylethan-1-amine
Synonyms	1-amino-2-phenylethane
CAS Number	64-04-0^Y
PubChem (CID)	1001
IUPHAR/BPS	2144
DrugBank	DB04325^Y
ChemSpider	13856352^Y
UNII	327C7L2BXQ^Y
KEGG	C05332^Y
ChEBI	CHEBI:18397^Y
ChEMBL	CHEMBL610^Y
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)
SMILES c1ccc(cc1)CCN
InChI InChI=1S/C8H11N/c9-7-6-8-4-2-1-3-5-8/h1-5H,6-7,9H2^Y Key:BHHGXPLMPWCGHP-UHFFFAOYSA-N^Y

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.