A new, potent, conformationally-restricted analog 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-(-)....

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Bibliographic Details
Published inJournal of medicinal chemistry Vol. 25; no. 5; pp. 535 - 538
Main Authors Hathaway, Bruce A, Nichols, David E, Nichols, Maxine B, Yim, George K. W
Format Journal Article
LanguageEnglish
Published United States American Chemical Society 01.05.1982
Subjects
2-Naphthylamine - analogs & derivatives
2-Naphthylamine - chemical synthesis
alpha-Methyltyrosine
Amphetamines
Animals
Central Nervous System Stimulants - chemical synthesis
Chemical Phenomena
Chemistry
Humans
Male
Methyltyrosines - pharmacology
Mice
Molecular Conformation
Motor Activity - drug effects
Naphthalenes - chemical synthesis
Rats
Rats, Inbred Strains
Reserpine - pharmacology
Stereotyped Behavior - drug effects
Time Factors
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Summary: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.
Bibliography:ark:/67375/TPS-58T4ZK2G-X
istex:CD3B8C8AF8402F52AA9C92192BABF15EEF061A9C
ISSN:0022-2623
1520-4804
DOI:10.1021/jm00347a011