Several permanently charged analogs of -chlorpromazine were synthesized and evaluated for their binding to dopamine D-2 receptors. In order to determine the molecular species, charged or uncharged, of dopamine agonists and antagonists that interact with the dopamine receptor, we have previously synthesized and studied permanently charged analogs of dopamine and chlorpromazine (1) on D-2 dopamine receptors in the striatum. Our results show that the quaternary ammonium (2) and sulfonium (3) compounds bind and produce agonist and antagonist activity while the permanently uncharged methyl sulfide analog (4) was devoid of either agonist or antagonist activity. However, an interesting observation has been made that, although active, the permanently charged analogs of both agonists and antagonists are less active than the corresponding parent primary, secondary or tertiary amine. One explanation that we have put forth is that permanently charged agonist or antagonist analogs only bind through an ionic bond with the receptor while protonated amines may bind with the receptor through a reinforced ionic bond (a combination of both an ionic and hydrogen bond) and thus show a higher affinity for the D-2 receptor. We hypothesized that it should be possible to enhance the activity of permanently charged analogs of chlorpromazine by adding a hydrogen bonding functional group in the region of the permanent positive charge. In this paper we report the synthesis of two permanently charged chlorpromazine aza analogs, 5 and 6, which have the potential for hydrogen bonding, and the comparative binding of these analogs to that of parent chlorpromazine (1) and the quaternary salt (2) on dopamine D-2 receptors.