Structural requirements for adrenergic alpha-receptorcovalent occupancy by chiral tetramine disulfides

Chiral tetramine disulfldes 3, designed to study the molecular properties of the active site of the adrenergic alpha-receptor, were synthesizedand tested on ral vas deferens preparation. The activity of the three optical isomers showed that the receptor displays an insignificantdegree ol stereoselectivity thus supporting the hypothesis that the benzylic groups of tetramine disulfides related to Benextramine donot bind at the same site that is normally occupied by the catechol nuclei of the neurotrirnsmitter. Rather, they would interact withan accessory area which appears to be insensitive to chirality efiects.