A new, potent, conformationally restricted analogue of amphetamine: 2-amino-1,2-dihydronaphthalene.
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 alpha-methyl-p-tyrosine antagonized the stimulation produced by 2-ADN.
D015081:2-Naphthylamine / Q000031:analogs & derivatives / Q000138:chemical synthesis*; D000662:Amphetamines; D000818:Animals; D000697:Central Nervous System Stimulants / Q000138:chemical synthesis*; D055598:Chemical Phenomena; D002621:Chemistry; D006801:Humans; D008297:Male; D008781:Methyltyrosines / Q000494:pharmacology; D051379:Mice; D008968:Molecular Conformation; D009043:Motor Activity / Q000187:drug effects; D009281:Naphthalenes / Q000138:chemical synthesis*; D051381:Rats; D011919:Rats, Inbred Strains; D012110:Reserpine / Q000494:pharmacology; D013239:Stereotyped Behavior / Q000187:drug effects; D013997:Time Factors; D019805:alpha-Methyltyrosine
D000662:Amphetamines; D000697:Central Nervous System Stimulants; D008781:Methyltyrosines; D009281:Naphthalenes; D019805:alpha-Methyltyrosine; C034494:2-amino-1,2-dihydronaphthalene; D012110:Reserpine; D015081:2-Naphthylamine