Erowid References Database
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Domelsmith LN, Munchhausen LL, Houk KN.
“Photoelectron Spectra of Psychotropic Drugs. 1. Phenethylamines, Tryptamines, and LSD”.
J.Am.Chem.Soc.. 1977 /;99(13):4311-21.
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Abstract
The photoelectron spectra of ,3-phenethylamine (1) and 10 analogs (2-11), of tryptamine (1Z) arid 7 analogs (indole, 13-18) and of LSD were studied. The spectra of these compounds were discussed in detail. The changes in ionization potentials (IP's) in the series were interpreted in terms of the influence of substituents on the mole cular orbital energies. The first IN (IP1) and the average of the first and second IP's (IPav) of the following compounds were plotted against the minimum effective brain level (MEBL) to alter rat behavior in a conditioned avoidance response: (19, 18, 17, 14 7, 6, 5, 10, 1 and 12 after MAO inhibition). IPav correlated more closely with activity than IP1, but the activites of tryptamines were less well correlated by IPav than were the activities of phenethylamines. It was noted that drugs with low IPav's are recognized hallucinogens. A correlation between IPav and activities (MEBL's) of these drugs is consistent with perturbation or charge transfer models of reactivity. It was suggested that there is probably a significant relationship between behavioral activity (at least in rats) and the electron-donating ability of the phenethylamines and tryptamineS. Studies on a wider range of phenethylamines and tryptamines are in progress to determine whether a quantitative relationship between hallucinogenic activity and IN can be established.
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