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Sapper H, Lohmann W. 
“Self-association and Binding Sites of Some Psychotomimetic Tryptamine Derivatives and Related Compounds: Nuclear Magnetic Resonance Investigations”. 
Mol.Pharmacol.. 1976;12(4):605-11.
Abstract
An NMR spectral study of binding sites in the self asacciation of various psychotomimetic drugs is described. Methods The NMR spectra of N,N-dimethyltryptamine (DMT), bufotenine, 5-hydroxytryptamine (HT), mescaline (all from Fluka), 6-hydroxytryptamine, psilocin and LSD (Sandoz) were recorded in deuterated phosphate buffer (pD 7.4) except for LSD which waa in acetate buffer (pD 5.4) using 2,2,3,3-tetradeutero-3trimethylsilylpropionate as internal reference. Self-association of LSD was more pronounced than that of DMT, HT and mescaline. Association of LSD molecules appeared to involve separation of the positively charged N(6) atoms so that the ring systems interacted with each other. The rotational abilities of the side-chains of the other compounds examined preclude direct ring-ring interactions. With the tryptamine derivatives and mescaline an alignment of the amino group at the end of the side-chain with the ring system of a neighboring molecule occurred. The side-chain amino group appeared to be the preferred site of aolvent solute interactiona. These spectral studies indicated that the mechanism of action on the receptor of LSD may be different from that of other psychotomimetics.
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