Article ID | Journal | Published Year | Pages | File Type |
---|---|---|---|---|
1377227 | Bioorganic & Medicinal Chemistry Letters | 2006 | 4 Pages |
Electron-withdrawing substituents at position 4 of 2,5-dimethoxy-substituted amphetamines increase, whereas electron-donating substituents decrease the psychotomimetic activity. The origin of this clearly localized effect is discussed. The uses of modified Hammett substituent scales (σ− and σ+), and especially the good σ+ correlation, strongly suggest that electron-donating substituents decrease the biological activity through a specific effect relating to the extent of the conjugative electron release from the 5-methoxy group to the phenyl ring.
Graphical abstractElectron-donating substituents decrease the psychotomimetic activity trough a specific effect relating to the diminution of the conjugative electron release from the 5-methoxy group to the phenyl ring.Figure optionsDownload full-size imageDownload as PowerPoint slide