Steric effects of substituents on phenethylamine hallucinogens. 3,4-(Methylenedioxy)amphetamine analogues alkylated on the dioxole ring.
The compounds 1-(2-methyl-1,3-benzodioxol-5-yl)-2-aminopropane and 1-(2,2-dimethyl-1,3-benzodioxol-5-yl)-2-aminopropane were synthesized and evaluated for pharmacologic effects in mice. These can be viewed as analogues of the known psychotomimetic agent 3,4-(methylenedioxy)amphetamine (MDA). Their hydrochloride salts were compared with MDA for their ability to increase spontaneous motor activity and to elicit behavioral effects. The former compounds was MDA-like in action, while the latter was not. The results suggest that one face of the molecule must be free of steric bulk to possess activity.
D015104:3,4-Methylenedioxyamphetamine / Q000031:analogs & derivatives / Q000138:chemical synthesis* / Q000494:pharmacology; D000662:Amphetamines / Q000138:chemical synthesis*; D000818:Animals; D001522:Behavior, Animal / Q000187:drug effects; D055598:Chemical Phenomena; D002621:Chemistry; D003292:Convulsants; D051379:Mice; D009043:Motor Activity / Q000187:drug effects
D000662:Amphetamines; D003292:Convulsants; D015104:3,4-Methylenedioxyamphetamine