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 via OpenAlex
Summary
AI-generated from the abstractA series of new chemical compounds similar to a known hallucinogen were synthesized and tested in animals. Most of the analogues showed low hallucinogenic potential. The compounds were compared with a reference substance in a behavioral model that distinguishes hallucinogenic from non-hallucinogenic drugs. The chemical structures and their effects are discussed.
Study at a glance
| Characteristics | Preclinical study Peer reviewed |
|---|---|
| Population | Animals |
| Keywords | Hallucinogen Butane Stereochemistry Chemical synthesis Structure–activity relationship |
| Citations | 13 |
| Key finding | 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.