Steric and Electronic Relationships among Some Hallucinogenic Compounds
Sungzong Kang, Jack Peter Green
Proceedings of the National Academy of Sciences September 1, 1970 DOI: 10.1073/pnas.67.1.62 (opens in new tab)
Study at a glance
AI-extracted from the abstract| Characteristics | Theoretical or philosophical paper Peer reviewed |
|---|---|
| Topics | LSD Mescaline |
| Keywords | Hallucinogen Steric effects Stereochemistry Pyrrole Heteroatom Ring chemistry Receptor Organic chemistry Pharmacology Biochemistry |
| Citations | 64 |
| Key points | Proposes that LSD, indolealkylamines, and methoxylated amphetamines share stereochemical and electronic features that allow them to interact with a common receptor via π-molecular and donor-acceptor complexes. |
Abstract
Stereochemical considerations and total valence electron calculations suggest congruities among the ostensibly dissimilar hallucinogenic compounds, D-lysergic acid diethylamide (LSD), indolcalkylamines, and methoxylated amphetamines. In LSD the aromatic benzene ring A and the N-6 nitrogen are essential for hallucinogenic activity; these sites may react with the receptor. The conformations of amphetamines and indolealkylamines at the receptor are such that the aromatic benzene ring lies like ring A of LSD and the alkylamino nitrogen lies like the N-6 of LSD. Ring A may interact with the receptor by forming a π-molecular complex, as suggested by the correlation between hallucinogenic activity and energy of the highest occupied molecular orbital ( E H ) of congeneric series. The N-6 nitrogen of LSD and the sterically congruent nitrogen of the other hallucinogenic compounds may react with the receptor by forming a donor acceptor complex of the n -π * or n -σ * type. Other portions of the hallucinogenic molecules confer a favorable E H : these include the methoxy and hydroxyl groups of the amphetamines (and mescaline), and the indolealkylamines; and the pyrrole ring of LSD and the indolealkylamines.
Comparable studies
Other theoretical and historical papers on mescaline, most cited first.
| Study | Year | Design | Participants |
|---|---|---|---|
| Schizophrenia: A New Approach. II. Result of a Year's Research | 1954 | Theoretical or philosophical paper | |
| Thought insertion as a self-disturbance: An integration of predictive coding and phenomenological approaches | 2016 | Theoretical or philosophical paper | |
| Entactogens: How the Name for a Novel Class of Psychoactive Agents Originated | 2022 | Theoretical or philosophical paper | |
| EFFECT OF DRUGS One individual | 1952 | Theoretical or philosophical paper | n = 1 |
| Writing on drugs | 2001 | Theoretical or philosophical paper |
Citations in the library
Cited by 10
- Repeated lysergic acid diethylamide in an animal model of depression: Normalisation of learning behaviour and hippocampal serotonin 5-HT2 signalling Journal of Psychopharmacology April 30, 2014
- THE NATURE OF THE BINDING BETWEEN LSD AND A 5‐HT RECEPTOR: A POSSIBLE EXPLANATION FOR HALLUCINOGENIC ACTIVITY British Journal of Pharmacology June 1, 1974
- Stereospecific Actions of DOET (2,5-Dimethoxy-4-Ethylamphetamine) in Man Archives of General Psychiatry July 1, 1974
- A new view of the structural relationship between LSD and mescaline Brain Research Bulletin May 1, 1977
- A crystallographic and theoretical study of the conformation of DOET and its significance for the hallucinogenic amphetamines Journal of Pharmacy and Pharmacology 1975
and 5 more in the library