C6H5CH2CH2NH2

C6H5CH2CH2NH2, commonly called phenethylamine (β-phenylethylamine), is an organic compound that consists of a benzene ring attached to a two-carbon chain terminating in an amino group. Its molecular formula is C8H11N and its systematic IUPAC name is 2-phenylethylamine. The structure is often depicted as Ph-CH2-CH2-NH2.

In biology, phenethylamine is produced by decarboxylation of the essential amino acid phenylalanine and occurs in trace levels in some foods and beverages. It is also present in the human brain as a trace amine, where it can interact with trace amine-associated receptors (TAARs) and influence dopaminergic signaling, though its exact physiological role is not fully defined.

Properties: It is a basic, primary amine; forms salts with acids; highly soluble in water and many organic solvents; exists as a colorless liquid at room temperature. It has a conjugate acid pKa of about 9–10, reflecting its moderate basicity.

Applications: Phenethylamine serves as a versatile building block in organic synthesis and pharmaceutical research. It is the core structure for many biologically active phenethylamines, including neurotransmitter precursors and synthetic analogs; related compounds include amphetamine derivatives, dopamine precursors, and various pharmaceutical intermediates.

Safety: As a primary amine, it is a irritant and basic; may be harmful if inhaled or absorbed through the skin and should be handled with gloves and eye protection. It is generally stored away from oxidizers and incompatible materials.