A quantum-chemical and experimental study of the hallucinogen (k)- 1-(2,5-dimethoxy-4-nitrophenyl)-2-aminopropane (DON)

Abstract

The electronic structure of 1-(2,5-dimethoxy-4-nitrophenyl)-2-aminopropane (DON) was calculated at the CND0/2 level, and the racemic compound was synthesized and found to be hallucinogenic at doses of 4 mg. DON differs from its similarly active congeners in that a hydrophilic nitro group replaces lipophilic substituents at C-4 of the benzene ring. The implications for the mechanism of serotonin receptor binding of these drugs are discussed.