Stereoselective pharmacological effects of lysergic acid amides possessing chirality in the amide substituent.

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.