Phenethylamine
Phenethylamine is the simplest compound of its namesake chemical class, a naturally occurring stimulant found throughout nature in both plants and animals, including as a notable component of chocolate.12 It is closely related structurally to amphetamine and several neurotransmitters.34 Despite its intrinsic stimulant properties, phenethylamine is rapidly and completely metabolized in the human body, which largely prevents it from expressing meaningful pharmacological activity when consumed on its own.35
Contents
Dosage & Duration
Dosage
Duration
Subjective Effects
Phenethylamine is notable for producing essentially no subjective effects when taken on its own, despite being intrinsically a stimulant. Human trials at oral doses of up to 1,600 mg and intravenous doses of up to 50 mg reported no effects whatsoever. This inactivity is attributed to its rapid and complete metabolism in the body, primarily by monoamine oxidase, which destroys the compound before its stimulant properties can be expressed.
Reagent Testing
Loading reagent data
Pharmacology
Pharmacodynamics
Phenethylamine acts as a releasing agent of norepinephrine and dopamine, with in vitro potency at these targets roughly comparable to amphetamine.6 It is a potent agonist at trace amine-associated receptor 1 (TAAR1)3 and inhibits vesicular monoamine transporter 2 (VMAT2) in monoamine neurons.7 In addition to its catecholamine-releasing activity, phenethylamine functions as a monoaminergic activity enhancer, increasing the action potential-mediated release of serotonin, norepinephrine, and dopamine at concentrations lower than those required for direct catecholamine release.8
Pharmacokinetics
Phenethylamine is extremely rapidly metabolized, with an oral half-life of only 5 to 10 minutes. A significant portion of orally ingested phenethylamine is degraded in the small intestine by monoamine oxidase B (MAO-B) followed by aldehyde dehydrogenase (ALDH), producing phenylacetic acid as the primary urinary metabolite. Additional metabolizing enzymes in humans include MAO-A, phenylethanolamine N-methyltransferase (PNMT), the semicarbazide-sensitive amine oxidases AOC2 and AOC3, flavin-containing monooxygenase 3 (FMO3),9 and aralkylamine N-acetyltransferase (AANAT). This extensive and rapid enzymatic breakdown accounts for phenethylamine's negligible oral psychoactivity under normal conditions, though activity can emerge in the presence of a monoamine oxidase inhibitor.
Tolerance
Harm Potential
Addiction & Dependence
Toxicity
Acts as a potent antimicrobial against certain pathogenic strains of Escherichia coli, including the O157:H7 strain, at sufficient concentrations.10
History & Culture
Phenethylamine has long held a special place in psychopharmacological research due to its status as the simplest member of the phenethylamine chemical class. Its clean molecular structure, natural presence in human tissues and bodily fluids, and close chemical relationship to both amphetamine and…
Legality
By Country
References
Source Pages
Comparative effects of amphetamine, phenylethylamine and related drugs on dopamine efflux, dopamine uptake and mazindol binding.
DrugBank: Phenethylamine
DrugBank: Phenethylamine BioEntity
Erowid: PiHKAL Entry #142 PEA
Isomer Design (TiHKAL/PiHKAL)
PsychonautWiki: Phenethylamine (compound)
TripSit Factsheet: Phenethylamine
Wikipedia
Wikipedia: TAAR1
Citations
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