Phenylalkylamines with potential psychotherapeutic utility. 2. Nuclear substituted 2-amino-1-phenylbutanes
- 1 February 1980
- journal article
- research article
- Published by American Chemical Society (ACS) in Journal of Medicinal Chemistry
- Vol. 23 (2) , 154-162
- https://doi.org/10.1021/jm00176a010
Abstract
A series of 2-amino-1-(4-substituted-2,5-dimethoxyphenyl)butanes was prepared as analogs of (R)-2-amino-1-(2,5-dimethoxy-4-methylphenyl)butane (1a) [dimoxamine, BL-3912A]. 1-(2,5-Dimethoxyphenyl)-2-(N-phthalimido)butane was used as a synthetic intermediate common to many target compounds. Animal [cat and rat] data indicate that most analogs 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 [4-methyl-2,5-dimethyoxy-.alpha.-methylphenethylamine] and DOET [2,5-dimethoxy-4-ethylamphetamine]. Structure-activity relationships of these analogs are discussed.This publication has 5 references indexed in Scilit:
- Synthesis and body distribution of several iodine-131-labeled central nervous system active drugsJournal of Medicinal Chemistry, 1977
- In vitro O-demethylation of the psychotomimetic amine, 1-(2,5-dimethoxy-4-methylphenyl)-2-aminopropaneJournal of Medicinal Chemistry, 1977
- Behavioral comparisons of R-2-amino-1-(2,5-dimethoxy-4-methylphenyl) butane (BL-3912A) with R-DOM and S-AmphetaminePsychopharmacology, 1977
- Phenylalkylamines with potential psychotherapeutic utility. 1. 2-Amino-1-(2,5-dimethoxy-4-methylphenyl)butaneJournal of Medicinal Chemistry, 1976
- COMPARISON OF EFFECTS OF R-(-)-2-AMINO-1-(2,5-DIMETHOXY-4-METHYLPHENYL) PROPANE (DOM), R-(-)-2-AMINO-1-(2,5-DIMETHOXY-4-METHYLPHENYL) BUTANE (BL-3912A) AND 5-HYDROXYTRYPTAMINE ON NON-INNERVATED VASCULAR SMOOTH-MUSCLE1976