Effect of 4-substitution on psychotomimetic activity of 2,5-dimethoxy amphetamines as studied by means of different substituent parameter scales

Bioorganic & Medicinal Chemistry Letters
Kari NeuvonenFerenc Fülöp

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 (sigma(-) and sigma(+)), and especially the good sigma(+) 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.

References

Aug 5, 1999·Neuropsychopharmacology : Official Publication of the American College of Neuropsychopharmacology·G K Aghajanian, G J Marek

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Citations

Sep 22, 2009·Forensic Science International : Synergy·Hadir M MaherC Randall Clark
Aug 15, 2013·Rapid Communications in Mass Spectrometry : RCM·Karolina Sekuła, Dariusz Zuba
Feb 11, 2011·Organic & Biomolecular Chemistry·María Rodríguez-MataVicente Gotor

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