A new, potent, conformationally restricted analogue of amphetamine: 2-Amino-1,2-dihydronapthalene

Article abstract of DOI:10.1021/jm00347a011

A new stimulant compound, 1,2-dihydro-2-naphthalenamine (2-amino-1,2-dihydronaphthalene, 2-ADN), was prepared as an analogue of amphetamine and of 2-aminotetralin. The optical isomers of 2-ADN were obtained by chemical resolution, and the absolute configuration was determined to be R-(+) and S-(-). Preliminary pharmacological evaluation revealed that racemic 2-ADN is approximately one-fourth as potent as (+)-amphetamine as a stimulant in mice. The S-(-) isomer of 2-ADN was found to be solely responsible for the stimulant effects of the racemate. Both reserpine and α-methyl-p-tyrosine antagonized the stimulation produced by 2-ADN.