The effect of changes in molecular configuration on inhibitory sympathomimetic action

Studies on Tetrahydroisoquinolines (Thi) (I) Bronchodilator Activity and Structure-Activity Relationship

“…The structure-activity relationship of catecholamines, the representative 9-adrenergic stimulants, has been studied for many years by several investigators (11)(12)(13)(18)(19)(20)(21)(22)(23)(24)(25)(26)(27). Based on the results of these investigations, it is generally accepted that the catecholic hydroxyl groups at position 3 and 4 are essential for manifestation of the Q-adrenergic activity (11-13).…”

The Research Behind Terbutaline

“…One of the compounds was isoetharine with an isopropyl group on the amino nitrogen. The other compound with a cyclopentyl group in the same nitrogen position (compound 111 in Lands & Brown, 1964) had previously been reported as WIN 713 (Lands & Tainter, 1953). Both compounds were highly selective for the lung tissue and also potent bronchodilators.…”

“…The crucial question was why a compound such as WIN 5591 was not developed further for use as a bronchodilator? To validate the results reported by Lands and Tainter (1953) my chemist colleagues, Kjell Wetterlin and Leif-A. Svensson, synthetized the Selvi compound (S63) with a cyclopentyl group on the amino nitrogen instead of the iso-butyl group (KWD 2001).…”

“…One of the papers was of special interest. It was a study by Lands and Tainter (1953): "The effect of changes in molecular configuration on inhibitory sympathomimetic action". By variation of the substituent on the amino nitrogen in catecholamines they could separate effect on heart (positive chronotropic and inotropic effects) from effect on lung (tracheobronchial smooth muscle relaxation).…”

The Influence of Some β‐Adrenergic Stimulant Compounds on Intestinal Motility in Vitro and in Vivo in Mice

“…The present study deals with a comparative evaluation of the effect of four p-adrenergic stimulant compounds on the intestinal tract in mice. The drug terbutaline (bricanylm) (BERGMAN et al 1969;PERSON & OLSSQN 1970;PERSSON & JOHNSON 1970) has been compared with the structurally related orciprenaline, dl-isoprenaline, andKWD 2026 (LANDS &TAINTER 1953). Isoprenaline (IPR)…”