phenylalkylamine

Phenylalkylamines, commonly referred to as phenethylamines, are a broad class of organic compounds defined by a phenyl ring attached to an alkyl chain bearing an amine group. The core skeleton is typically the phenethylamine structure (Ar-CH2-CH2-NH2), with many derivatives formed by substituting the aromatic ring or adjusting the side chain. This framework includes both naturally occurring monoamines such as dopamine, norepinephrine, and epinephrine, and a wide range of synthetic compounds used in medicine or encountered as psychoactive drugs.

Substitutions on the benzene ring and along the side chain generate diverse pharmacological profiles. Simple phenethylamines can be further modified to give amphetamine-type compounds (alpha-methylphenethylamines), as well as a family of substituted phenethylamines that include psychedelic and empathogenic agents. Examples commonly cited in pharmacology and toxicology include phenethylamine (the parent compound), amphetamine, methamphetamine, mescaline, MDMA (3,4-methylenedioxymethamphetamine), and members of the 2C family such as 2C-B. Endogenous examples such as dopamine illustrate the natural occurrence of this motif in the nervous system.

Pharmacologically, phenylalkylamines principally modulate monoamine neurotransmission, acting as substrates for, or inhibitors of, transporters for dopamine, norepinephrine, and serotonin. Substitution patterns influence potency, selectivity, and central nervous system effects, which range from stimulant and mood-enhancing to hallucinogenic. Due to potential for abuse and health risks, many phenylalkylamines are regulated, with clinical uses concentrated in specific stimulant or decongestant medications and research contexts.