File:Phenethylamine2DCSD.svg · Wikimedia Commons · See Wikimedia Commons
2-phenethylamine
Sign in to saveAlso known as β-PEA, benzeneethanamine, 2-phenylethan-1-amine, 2-phenylethylamine, 1-phenyl-2-aminoethane, 2-phenylethanamine, β-phenethylamine, 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.
Key facts
- Drug.verifiedrevid
- 612854585
- Drug.IUPAC_name
- 2-Phenylethan-1-amine
- Drug.image
- Phenethylamine2DCSD.svg
- Drug.image_class
- skin-invert-image
- Drug.alt
- Image of the phenethylamine skeleton
- Drug.width
- 200
- Drug.image2
- Phenethylamine-3D-balls.png
- Drug.image_class2
- bg-transparent
- Drug.alt2
- Ball-and-stick model of phenethylamine
- Drug.width2
- 200
- Drug.routes_of_administration
- Oral
- Drug.class
- Norepinephrine–dopamine releasing agent; Trace amine-associated receptor 1 (TAAR1) agonist; Stimulant
- Drug.dependency_liability
- Psychological: Low–moderatePhysical: None
- Drug.addiction_liability
- None–low (w/o an MAO-B inhibitor)Moderate (with an MAO-B inhibitor)
- Drug.source_tissues
- Substantia nigra pars compacta;Ventral tegmental area;Locus coeruleus;many others
- Drug.target_tissues
- System-wide
- Drug.receptors
- Varies greatly across species;Human receptors: hTAAR1
- Drug.precursor
- L-Phenylalanine
via Wikipedia infobox
Chemical data
- Formula
- C8H11N
- Molecular weight
- 121.18 g/mol
- IUPAC name
- 2-phenylethanamine
- SMILES
- C1=CC=C(C=C1)CCN
- InChIKey
- BHHGXPLMPWCGHP-UHFFFAOYSA-N
- XLogP
- 1.4
- Polar surface area
- 26 Ų
- H-bond donors
- 1
- H-bond acceptors
- 1
- Formal charge
- 0
via PubChem
Research
1,753 papers- 2-Heteroarylethylamines in medicinal chemistry: a review of 2-phenethylamine satellite chemical space.Beilstein journal of organic chemistry · 2024
- Gut microbiota-derived tryptamine and phenethylamine impair insulin sensitivity in metabolic syndrome and irritable bowel syndrome.Nature communications · 2023
- Neurophysiological correlates of affiliative behaviour between humans and dogs.Veterinary journal (London, England : 1997) · 2003
- 2-Phenethylamines in Medicinal Chemistry: A Review.Molecules (Basel, Switzerland) · 2023
- Effect of Bulky N-Dibenzofuranylmethyl Substitution on the 5-HT(2) Receptor Affinity and Efficacy of a Psychedelic Phenethylamine.ACS chemical neuroscience · 2024
via PubMed
Wikidata facts
- Mass
- 121.089149
- Autonomy
- 425
Show 16 more facts
- Commons category
- Phenethylamine
- chemical formula
- C₈H₁₁N
- canonical SMILES
- C1=CC=C(C=C1)CCN
- melting point
- 0
- density
- 0.962
- boiling point
- 201
- refractive index
- 1.5290
- pKa
- 9.83
- partition coefficient water/octanol
- 1.41
- lower flammable limit
- 1
- upper flammable limit
- 5.5
- flash point
- 81
- vapor pressure
- 5.11
- solubility
- 4.3
- kinematic viscosity
- 2.40
- dynamic viscosity
- 2.4
via Wikidata · CC0
~15 min read
Article
22 sectionsContents
- Natural occurrence
- Chemistry
- Substituted derivatives
- Analogues
- Synthesis
- Detection in body fluids
- Pharmacology
- Pharmacodynamics
- Monoamine releasing agent
- TAAR1 agonist
- Monoaminergic activity enhancer
- Other activities
- Effects in animals and humans
- Pharmacokinetics
- History
- Society and culture
- Legal status
- United States
- See also
- Notes
- References
- External links
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 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 have postulated that phenethylamine plays a role in affection without substantiating these claims with any direct evidence.