Serotonin receptor affinity of cathinone and related analogues

A series of cathinone (alpha-aminopropiophenone) analogues was examined using the isolated rat fundus preparation. (S)-(-)-Cathinone possesses twice the serotonin receptor affinity of (+/-)-cathinone and four times the affinity of racemic amphetamine. Several derivatives of cathinone were found to either possess a lower affinity than the parent compound or did not interact with the receptors in a competitive manner. Several novel analogues, 1-(aminomethyl)-3,4-dihydronaphthalene hydrochloride (3), 4-(aminomethyl)-3-chromene hydrochloride (4b), as well as its 6-methoxy derivative, a, interact with serotonin receptors but in a fashion which is, most likely, dissimilar to the interaction of the substituted cathinone analogues.