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Photoelectron spectra of psychotropic drugs. III. Ionization potentials and partition coefficients as predictors of substituted amphetamine psychoactivities
Author(s) -
Domelsmith L. N.,
Houk K. N.
Publication year - 2009
Publication title -
international journal of quantum chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.484
H-Index - 105
eISSN - 1097-461X
pISSN - 0020-7608
DOI - 10.1002/qua.560140725
Subject(s) - chemistry , ionization , ionization energy , phenethylamines , partition coefficient , amphetamine , computational chemistry , x ray photoelectron spectroscopy , spectral line , stereochemistry , chromatography , organic chemistry , nuclear magnetic resonance , psychology , ion , physics , neuroscience , dopamine , astronomy
Abstract Ionization potentials have been measured by photoelectron spectroscopy for 14 substituted amphetamines and phenethylamines. Comparisons with STO‐3G calculations on various methoxylated benzene models indicate adequate agreement between calculated and experimental ionization potentials, but also reveal unexpected methoxy conformations in some of these species. Multiple regression analyses demonstrate the importance of both ionization potentials and lipophilicities, measured by 1‐octanol‐water partition coefficients, in determining psychotropic activities for a series of substituted amphetamines. The first and second π ionization potentials also correlate with differences in the abilities of a variety of psychotropic drugs to displace d ‐LSD from its high‐affinity binding site in rat brain homogenates.