Abstract
Molecular orbital calculations and classical potential function calculations were carried out to examine the proposal that the conformations of the hallucinogenic tryptamines and phenylalkylamines are such that their 6-membered aromatic rings and their alkylamino nitrogens are congruent with A ring and N(6) nitrogen atom of lysergic acid diethylamide (the nitrogen of the D ring). The congruent conformation of psilocin is Ψ{C(9)-C(3)-C(β)-C(α)} = 46 ± 10 degrees, φ{C(3)-C(β)-C(α)-N} = 230 ± 20 degrees, θ1{C(β)-C(α)-N-C(1N)} = 180 ± 10 degrees, and θ2{C(β)-C(α)-N-C(2N)} = 300 ± 10 degrees; that of mescaline is ψ{C(2)-C(1)-C(β)-C(α) = 147 ± 10 degrees and φ{C(l)-C[β]-C(α)-N} = 160 ± 20 degrees. These results show that congruence of psilocin and mescaline with lysergic acid diethylamide is energetically permissible.
ACKNOWLEDGMENT We thank Mr. Marian Strelcyzk for technical assistance.
- Copyright ©, 1973, by Academic Press, Inc.
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