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Pullman B, Courriere P, Berthod H. 
“Molecular Orbital Studies on the Conformation of Hallucinogenic Indolealkylamines and Related Compounds. The Isolated Molecules and the Solvent Effect.”. 
J Med Chem. 1974;17:439-447.
The conformation of hallucinogenic indolealkylamines and related compounds was studied. Methods The molecular orbital perturbative configuration interaction using localized orbitals (PCILO) was computed, using the quantum energy program exhange (Indiana University, Bloomington,Ind.). conformational energy map was constructed for each sub-group of the lndolealkyamines, using geometrical input data of a representative compound. Computations of torsion angles Al and hr were made in increments of 30°. Data are given for group (1) ionic derivatives with N Ha terminal group serotonin (creatine sulfate and pilrate) and tryptamine.HCl; group (2) neutral with NHz terminal, 5-methoxytryptamine; group (3) ionic with N'H(CH3)z terminal, 5-methoxy-N,N-dimethyltryptaminé, psilocybin and psilocine; and group (4) neutral with N(CH3):terminal, N-N-dimethyltryptamine and bufotenine.Melatonin, LSD, ibogaine, yohimban, cleavamine and reserpine, which do not fit into these subgroups were also evaluated. The effects of water on the conformation of 5-HT and bufotenin were determined using the microscopic super-molecular approach. hr suits NACHO, in contrast to the extended Hueckel theory, predicted a preference for a gauche form, with the plane of the side chain inclined with respect to the ring, for subgroup (1) compounds. The global energy minimum predicted by-the intermediate neglect differential overlap method, does not seem to be significant. Group (2) showed a strong preference for a perpendicular and fully ex-tended conformation. Group (3) showed a preference for a perpen-dicular and gauche conformation. Group (4) are predicted to prefer a perpendicular or a strongly inclined side-chain with respect to the ring. Hydration produces a smoothing-out of the energy diff-erences between the preferred conformers of the rationing forms, particularly those with N Ha cationic lead. The bans ( T2 = iS0°) and gauche ( T2 + 60°) conformers are of nearly equal energy and should coexist in solution.
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