Conformationally restricted analogs of histamine H1 receptor antagonists: trans and cis 1 benzyl 3 dimethylamino 6 phenylpiperidine

Article abstract of DOI:10.1021/jm00223a020

The syntheses of trans and cis 1 benzyl 3 dimethylamino 6 phenylpiperidine (1 and 2) are described. Compounds 1 and 2 were found to be inhibitors of histamine, acetylcholine, and barium chloride induced contractions of the isolated guinea pig ileum. Compounds 1 and 2 do not exhibit appreciable stereoselectivity in their ability to inhibit smooth muscle contractions. The cis compound 2 is a more effective inhibitor of histamine N methyltransferase than the trans isomer 1.