title: Stereoselective pharmacological effects of lysergic acid amides possessing chirality in the amide substituent.
abstract: Studies of the affinities for serotonin 5-HT2A and 5-HT1A receptor subtypes of lysergic acid amides prepared from chiral 2-aminoalkanes showed a stereoselective preference at both receptor types for the amides with alkyl groups containing the R configuration. The 5-HT2A receptor was less tolerant of long alkyl groups than was the 5-HT1A subtype. In vivo assays in rats trained to discriminate LSD from saline also showed that amides with alkyl groups having the R configuration were most potent.
authors.affiliation: Department of Medical Chemistry and Pharmacognosy, Purdue University, West Lafayette, IN 47907, USA. drdave@sage.cc.purdue.edu
authors.forename: D E
authors.initials: DE
authors.lastname: Nichols
authors.forename: A
authors.initials: A
authors.lastname: Monte
authors.forename: X
authors.initials: X
authors.lastname: Huang
authors.forename: D
authors.initials: D
authors.lastname: Marona-Lewicka
mesh_terms: D000818:Animals; D006801:Humans; D008237:Lysergic Acid / Q000737:chemistry* / Q000494:pharmacology*; D008238:Lysergic Acid Diethylamide / Q000737:chemistry* / Q000494:pharmacology*; D051381:Rats; D011985:Receptors, Serotonin / Q000187:drug effects*; D012702:Serotonin Antagonists / Q000737:chemistry* / Q000494:pharmacology*; D017366:Serotonin Receptor Agonists / Q000737:chemistry* / Q000494:pharmacology*; D013237:Stereoisomerism; D013329:Structure-Activity Relationship
chemical_list: D011985:Receptors, Serotonin; D012702:Serotonin Antagonists; D017366:Serotonin Receptor Agonists; D008238:Lysergic Acid Diethylamide; D008237:Lysergic Acid