Phenylalkylamines with potential psychotherapeutic utility. 2. Nuclear substituted 2-amino-1-phenylbutanes
Robert T. Standridge, Henry G. Howell, Hugh A. Tilson, J. Chamberlain, Henry M. Holava, Jonas A. Gylys, R. A. Partyka, Alexander T. Shulgin
Journal of Medicinal Chemistry February 1, 1980 DOI: 10.1021/jm00176a010 (opens in new tab)
Study at a glance
AI-extracted from the abstract| Characteristics | Preclinical study Peer reviewed |
|---|---|
| Population | Animals |
| Keywords | Hallucinogen Butane Stereochemistry Chemical synthesis Structure–activity relationship Plant-based medicinal research |
| Citations | 13 |
| Key points | Most of the synthesized analogues of (R)-2-amino-1-(2,5-dimethoxy-4-methylphenyl)butane have low hallucinogenic potential in animal models. |
Abstract
A series of 2-amino-1-(4-substituted-2,5-dimethoxyphenyl)butanes (Table V) was prepared as analogues of (R)-2-amino-1-(2,5-dimethoxy-4-methylphenyl)butane (1a). 1-(2,5-Dimethoxyphenyl)-2-(N-phthalimido)butane (7) was utilized as a synthetic intermediate common to many of the target compounds. Animal data are presented indicating that most of these analogues have low hallucinogenic potential. Selected compounds were compared with 1a in an avoidance-response acquisition model which differentiates between 1a and the human hallucinogens DOM (2a) and DOET (2b). Structure-activity relationships of these analogues are discussed.