Dihydrobenzofuran Analogues of Hallucinogens. 3. 1 Models of 4-Substituted (2, 5-Dimethoxyphenyl) alkylamine Derivatives with Rigidified Methoxy Groups 2

AP Monte, D Marona-Lewicka, MA Parker…

Index: Monte, Aaron P.; Marona-Lewicka, Danuta; Parker, Matthew A.; Wainscott, David B.; Nelson, David L.; Nichols, David E. Journal of Medicinal Chemistry, 1996 , vol. 39, # 15 p. 2953 - 2961

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Citation Number: 104

Abstract

Tetrahydrobenzodifuran functionalities were employed as conformationally restricted bioisosteres of the aromatic methoxy groups in prototypical hallucinogenic phenylalkylamines 1 and 2. Thus, a series of 8-substituted 1-(2, 3, 6, 7-tetrahydrobenzo [1, 2- b: 4, 5-b'] difuran-4-yl)-2-aminoalkanes (7a-e) were prepared and evaluated for activity in the two-lever drug discrimination paradigm in rats trained to discriminate saline from LSD ...