Amphetamine structure-activity relationships

MDMA is believed to have unique psychoactive properties that clearly distinguish it from hallucinogenic or psychostimulant phenethylamines. Not only have MDMA users consistently reported this distinctiveness, but subsequent studies of MDMA and similar compounds, in many laboratories, have shown that they do not fit within the structure-activity relationships that presently are understood to define the hallucinogenic amphetamines. 

Thus, for this class of psychoactive agent, prehminary structure-activity relationships are being formulated. Currently, four structural features eontrast the structure-activity relationships of entactogens with those of hallueinogenie amphetamines. 

Woolverton, W.L. Shybut, G. and Johanson, CE. Structure-activity relationships among some t(-N-alkylated amphetamines. Pharmacol Biochem Behav 13 869-876, 1980. 

AMPHETAMINE-LIKE STRUCTURE-ACTIVITY RELATIONSHIPS Aromatic Substituents... 

Fuller, R.W. Structure-activity relationships among the halogenated amphetamines. Ann NY Acad Sci 305 147-159, 1978. 

Hansch and Caldwell have analyzed the quantitative structure/activity relationships (QSAR) of a series of amphetamine and 2-phenethylamine analogs, to discern the role of steric and hydrophobic aryl substituents on the inhibition of 5-HT uptake (142). From the biological data of 19 compounds, including those in Table 15.13. and some additional analogs, the following equation was derived for inhibition of uptake activity, where C is the IC concentration, MR4 is the molar refrac-tivity value of the aryl substituent scaled by 0.1, and 7T3 is the hydrophobicity of the meUi substituent on the aryl ring ... 

The discovery that tryptamine is also an endogenous enhancer substance (Knoll 1994) opened the way for a structure-activity relationship study aiming to synthesize a new family of enhancer compounds structurally unrelated to PEA and the amphetamines. J -(-)-l-(benzofuran-2-yl)-2-propylaminopen-tane [ (-)-BPAP ] was selected as a tryptamine-derived synthetic mesencephalic... 

Structure-Activity Relationships for Amphetamine-like Stimulant Action... 

Chemistry - In contrast to the efforts in the field of antidepressants, relatively little work on central stimulants was reported. The structure-activity relationship of amphetamine derivatives was studied by a molecular orbital method 74. xhe greatest central stimulant effect was associated with those compounds having the lowest negative charge on the ring carbon atom ortho to the side-chain and with the lowest dipole moment arising from... 

Non-Phenethylamine Derivatives - The search for compounds which bear no structural relationship to phenethylamlnes and have anorectic properties continues. Current studies on Wy-5244 (XIV) show it to possess only weak sympathomimetic activity in isolated cat atria and rabbity aortic strips however the compound apparently does alter adrenergic receptor mechanisms since the actions of substances such as norepinephrine, d-amphetamine, phenoxybenzamine, and Imlpramine were profoundly influenced by Wy-5244.31 The synthesis of (XIV) and related compounds has been described.32... 

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