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Green JP, Johnson CL, Weinstein H, Kang S, Chou D. 
“Molecular Determinants For Interaction With The LSD Receptor: Biological Studies And Quantum Chemical Analysis”. 
Psychopharmacology of Hallucinogens. 1978;p28-60.
5-Hydroxytryptamine (5-HT) is widely distributed and potently active on many "tissues in some of which it appears to react with sites similar to those of D-lysergic acid diethylamide (D-LSD) and some other hallucinogenic compounds. For these reasons, a search for the molecular structural characteristics that determine the effects of these and related substances has attracted attention (Johnson et al. 1975; Green et al. 1974). About ten-years ago,efforts began to use quantum mechanics to learn the electronic characteristics of specific atoms tin the indole ring that could account for the activities of 5-HT and other tryptamines (Merril et al., 1966; Green, 1966, 1967). This work was given impetus with the availability of more sophisticated quantom mechanical methods. These were used to account quantitatively for the potencies of tryptamines on the D-LSD receptor in the fundus of the stomach (Green and Kanq, 1970). We describe here the results of studies on the potencies of tryptamines on three different biological systems and the molecular electronic correlates of the potencies. The biological measurements are: contraction of the fundus of the rat stomach; inhibition of high affinity binding of D-LSD to rat brain membranes; and inhibition of uptake of 5-HT by rat synaptosomes. Only the last lacks sensitivity to D-LSD. As well as doing total valence electron calculations, we studied the molecular reactivity of some of the tryptamines by new theoretical methods (Weinstein et al. 1974; Bartlett and Weinstein, 1975; Politzer and Weinstein, 1975; Chanq et al. 1976) using ab-initio calculations.
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