Steric effects of substituents on phenethylamine hallucinogens. 3,4-(Methylenedioxy)amphetamine analogues alkylated on the dioxole ring.
D E Nichols, L J Kostuba
Journal of Medicinal Chemistry October 1979 DOI: 10.1021/jm00196a022 (opens in new tab)
Study at a glance
AI-extracted from the abstract| Characteristics | Animal pharmacology experiment Peer reviewed |
|---|---|
| Population | Mice |
| Interventions | 1-(2-methyl-1 1-(2 2-dimethyl-1 3 4-(methylenedioxy)amphetamine (MDA) |
| Key findings | The 2-methyl benzodioxole analogue produced MDA-like increases in spontaneous motor activity and behavioral effects in mice, whereas the 2,2-dimethyl analogue did not. The authors suggest that one face of the molecule must be free of steric bulk for activity. |
Abstract
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.
Citations in the library
Cited by 3
- ECSTACY: A Review of MDMA and MDA The International Journal of Psychiatry in Medicine December 1, 1987
- Synthesis of fluoro analogues of 3,4-(methylenedioxy)amphetamine (MDA) and its derivatives. Chemistry & Biodiversity March 2006
- Studies of dioxole ring substituted 3,4-methylenedioxyamphetamine (MDA) analogues. Pharmacology, Biochemistry, and Behavior November 1989