Isomeric cyclopropyl ring-methylated homologs of trans-2-(2,5-dimethoxy-4-methylphenyl)cyclopropylamine, an hallucinogen analog
James N. Jacob, David E. Nichols
Journal of Medicinal Chemistry May 1, 1982 DOI: 10.1021/jm00347a009 via OpenAlex
Summary
AI-generated from the abstractAdding a methyl group at the 3-position of the cyclopropyl ring, in either the cis or trans orientation relative to the amino group, eliminated the activity of the hallucinogen analogue trans-2-(2,5-dimethoxy-4-methylphenyl)cyclopropylamine. Neither the cis nor the trans isomer showed appreciable activity in the mouse ear-scratch assay or in producing contraction in the rat fundus preparation, compared to the nonmethylated parent compound.
Study at a glance
| Characteristics | Experimental study Peer reviewed |
|---|---|
| Population | Mice and rats |
| Intervention | 5-dimethoxy-4-methylphenyl)cyclopropylamine |
| Keywords | Hallucinogen Stereochemistry Ring chemistry Pharmacology Organic chemistry |
| Citations | 6 |
| Key finding | Neither the cis nor the trans 3-methylated isomer of trans-2-(2,5-dimethoxy-4-methylphenyl)cyclopropylamine showed appreciable activity in the mouse ear-scratch assay or rat fundus preparation compared to the nonmethylated parent. |
Abstract
The hallucinogen analogue trans-2-(2,5-dimethoxy-4-methylphenyl)cyclopropylamine was modified by adding a 3-methyl group, either cis or trans with respect to the amino group. These two isomeric cyclopropyl ring-methylated compounds were then tested for activity in the mouse ear-scratch assay and for a contractile effect in the rat fundus preparation. Neither compound was found to possess appreciable activity when compared to the nonmethylated parent, in either assay.