A new view of the structural relationship between LSD and mescaline
David E. Nichols, William Pfister, G.k.w. Yim, Reilly Cosgrove
Brain Research Bulletin May 1, 1977 DOI: 10.1016/0361-9230(77)90034-x via OpenAlex
Summary
AI-generated from the abstractThe S-(-) enantiomer of 2-amino-1,2,3,4-tetrahydronaphthalene (2-AT) produces selective central effects in mice and rabbits that resemble those of hallucinogens such as mescaline. A stereochemical analysis of these findings suggests that the structural relationship between mescaline and other phenethylamine-type hallucinogens may involve a correspondence between the aromatic ring of the phenethylamines and the pyrrole portion of the indole nucleus in LSD.
Study at a glance
| Characteristics | Experimental study Peer reviewed |
|---|---|
| Population | Mice and rabbits |
| Interventions | 2 3 4-tetrahydronaphthalene R-(+) 2-amino-1 |
| Topics | Mescaline |
| Keywords | Hallucinogen Phenethylamines Tryptamines Enantiomer |
| Citations | 10 |
| Key finding | The S-(-) enantiomer of 2-AT shows selective central effects similar to hallucinogens like mescaline, and stereochemical analysis suggests a structural correspondence between phenethylamine aromatic rings and the pyrrole portion of LSD's indole nucleus. |
Abstract
An examination of the effects of S-(-) and R-(+) 2-amino-1,2,3,4-tetrahydronaphthalene (2-AT) on mouse spontaneous activity and rabbit EEG has shown that the S-(-) enantiomer shows selective central effects similar to those of hallucinogens like mescaline. A stereochemical analysis of these results indicates that the structural relationship between mescaline, or other phenethylamine type hallucinogens, may involve correspondence between the aromatic ring of the phenethylamines and the pyrrole portion of the indole nucleus in LSD.