A crystallographic and theoretical study of the conformation of DOET and its significance for the hallucinogenic amphetamines
Journal of Pharmacy and Pharmacology January 1, 1975 Alan S. Horn, Michael L. Post, Olga Kennard et al. 4 citations
The crystal structure of DOET, a psychedelic compound, was determined using X-ray crystallography. No hydrogen bonding was found in the solid state. The side chain of the molecule adopts a staggered position relative to the benzene ring, with the α-methyl group fully extended away from the ring and the amino group bent back toward it. Theoretical calculations revealed six possible side-chain positions with very small energy differences, one matching the crystal form. These findings are compared to the structures of related hallucinogens, mescaline and TMA.