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Domelsmith LN, Munchhausen LL, Elouk KN. 
“Lysergic Acid Diethylamide. Photoelectron Ionization Potentials as Indices of Behavioral Activity”. 
J.Med.Chem.. 1977;20(10):1346-48.
Abstract
A photoelectron spectral study of LSD was undertaken in order to relate ionization potential (IP) to biological activity. Photoelectron spectra of LSD and dimethyltryptamine (DMT) were run and the IP's located. LSD had 5 IP's between 7.25 and 9.75 eV arising from the aromatic portion of the molecule and IP's of 8.4 eV from the tertiary amine and 8.5-9.0 and 9.1 eV from the amide group. The lowest aromatic IP of LSD was significantly lower than that of DMT, whereas the first IP of LSD was not abnormally low compared to other good electron donors like phenothiazines. A plot of Vogel's minimum effective brain level (MEBL) causing behavioral changes in rats in a shuttlebox against average of the first and second IP was constructed. This indicated that drugs with low average IP were recognized hallucinogens, e.g. amphetamine, mescaline, LSD. A plot of average IP against ability to displace specifically bound 3H-d-LSD in rat brain homogenates showed an emerging correlation between increasing activity and decreasing average
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