A crystallographic and theoretical study of the conformation of DOET and its significance for the hallucinogenic amphetamines
Journal of Pharmacy and Pharmacology – January 01, 1975
Source: OpenAlex
Summary
The crystal structure of 2,5-dimethoxy-4-ethyl-α-methyl-phenylethylamine (DOET) reveals no hydrogen bonding in its solid state, with X-ray crystallography confirming a staggered isopropylamine side chain relative to the benzene ring. Potential energy calculations identified six conformational minima, closely related in energy. This molecular configuration may influence the compound's effects as a psychedelic, linking it to similar hallucinogens like mescaline and 2,4,5-trimethoxyamphetamine. Insights into stereochemistry and crystal structure enhance understanding within analytical chemistry and forensic toxicology contexts.
Abstract
Abstract The crystal and molecular structure of 2,5-dimethoxy-4-ethyl-α-methyl-phenylethylamine (DOET) has been determined by X-ray crystallography and the conformation of the side chain has been examined theoretically by the use of a potential energy calculation. There is no indication in the solid state of any intra or inter-molecular hydrogen bonding. The isopropylamine side chain is staggered to the plane of the benzene ring. The α-methyl group is fully extended (antiplanar) whereas the amino group is orientated back towards the ring (synclinal). The potential energy calculations show the existence of 6 minima, one of which corresponds to the crystal position. The calculations also show that the energy differences between the various minima of the side chain are very small. The relationship of these data to the conformations of the hallucinogens, mescaline and 2,4,5,-trimethoxyamphetamine is discussed.