TY - JOUR T1 - Self-association and Binding Sites of Some Psychotomimetic Tryptamine Derivatives and Related Compounds: Nuclear Magnetic Resonance Investigations JF - Molecular Pharmacology JO - Mol Pharmacol SP - 605 LP - 611 VL - 12 IS - 4 AU - H. SAPPER AU - W. LOHMANN Y1 - 1976/07/01 UR - http://molpharm.aspetjournals.org/content/12/4/605.abstract N2 - The nature of the binding sites in the self-association of some psychotomimetic drugs has been investigated by NMR techniques. In the case of d-lysergic acid diethylamide the interaction of the aromatic ring systems was found to be the basis of self-association (ΔH = -8.7 ± 0.7 kcal mole-1). In self-associates of the tryptamine derivatives and mescaline (ΔH = -3 to -4 kcal mole-1) the ring overlap of associated molecules may be replaced by an alignment of the amino group located at the end of the side chain with the ring system of a neighboring molecule. The influence of substitutions on the ring systems and special solvent-solute interactions is discussed. Whereas the amino group at the end of the side chain seems to be the preferred site of solvent-solute interactions, the locus of a hydroxyl substitution on the ring system seems to modify the stereochemistry of the self-associates. ER -