Article ID Journal Published Year Pages File Type
1377227 Bioorganic & Medicinal Chemistry Letters 2006 4 Pages PDF
Abstract

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

Related Topics
Physical Sciences and Engineering Chemistry Organic Chemistry
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